
These are just some of the things we love about Chicago. (Jacoby Cochran / City Cast)
Whether we're breaking down the news of the week, bringing you a neighborhood guide, or talking to important people — everything we do at Hey Chicago and City Cast Chicago is out of love for this city.
So in honor of the podcast's 1,000th episode, we (our staff, guests, readers, and listeners) have compiled a list of 1,000 things we love about Chicago.
“How much Chicagoans love Chicago!” — Megan M.
- “I LOVE how my city has ALWAYS been the Mecca of standards WORLDWIDE! From food to fashion to slang to vibes, Chicago has ALWAYS ran the show, and the world KNOWS that! ‘I just want somebody to love me like people from Chicago love Chicago’ 🗣️” — Jae B.
- Being the biggest city in the midwest
- "The small-town feel even though it's a large city" — Jordan S.
- Being “demure”
- Midwest friendliness
- Waving to boats on the river and people waving back
- "We never show up empty-handed." — Bob Ziltz, City Cast Chicago senior account executive
- "Our flag is literally the best." — Sidney Madden, former Hey Chicago newsletter editor
- Fierce neighborhood pride
- Learning from social media influencers who actually go to the South and West sides
- Neighborhood parades
- The Bud
- Skating in the Bud
- Pride Parade
- “My first Puerto Rican People’s Day parade.” — Jacoby Cochran, City Cast Chicago host
- Paseo Boricua
- Devon Street
- The Asia on Argyle sign (“Hope it's back soon!” — Simone Alicea, City Cast Chicago executive producer)
- Walking down 18th Street
- Large stuffed animals in Chinatown market shop windows
- 26th Street Shopping
- Window shopping on Rush street
- "We appreciate fashion! Concert or birthday, doesn't matter — Chicagoans will look our best." — Mariah McBride, City Cast marketing coordinator
- Opening up some fresh Mikes or G-Fazos
- “The commitment to community across the city.” — Jake S.
- The excitement when house music starts playing at the function
- Garage juke parties
- Parties in the garage and playing bags in the alley
- Fireworks in the alley
- "Just hang'n out and having a beer with friends and family is THE BEST Chicago 'event' — backyards, a garage, your church/parish, local bar, etc." — Bob Z.
- Having a tamborazo, mariachi or banda at a family party
- Family parties on the South Side
- Dan Ryan Woods BBQs
- “The community vibe” — Sharon D.
- “The blend of big city perks and tight-knit community vibes.” — Allison L.
- “The fact that people are open, willing, and eager to build community with each other!” — Cassidy W.
- "Lowkey board games: So many indie developers here." — Simone A.
- “The community and how everywhere you go random people are nice and willing to strike up a conversation.” — Krima P.
- "We all kind of collectively ride for each other, and ride for the bigger picture. It really does kind of feel like a small town." — Patrick Filbin, Block Club Chicago reporter
- All of the different flags around the city.
- "It’s less elitist than New York and LA." — Michelle Navarro, City Cast Chicago producer
- "We throw great benefit events for those in need." — Bob Z.
- DFSS Senior Fest
- "The mix of cynicism, perseverance, and intensity that drives politics and organizing." — Simone A.
- "Chicago is such a hardcore city when it comes to organizing." — Adriana Cardona-Maguidad, WBEZ reporter
- Reading “We Are The Culture” for the first time
- "The fact everyone knows our pension obligations are f*cked" — Jacoby C.
- "Our politics feeling like a real life TV show." — Michelle N.
- "It's pretty easy to vote in Chicago compared to a lot of other places in the country." — Sidney M.
- Working hard and playing equally hard
- Rollerskating at The Rink, Markham, Glenwood, MLK
- Day parties at Promontory
- "Going to Kingston Mines, regretting it, then eventually enjoying it again" — Wil Fulton, City Cast content director
- Running into friends at your local dive bar
- Dancing at Sidetrack
- The party raffle at My Buddy’s
- “Watching Jeopardy in a downtown gay bar on a Tuesday with my Tuesday club. It shows early in Chicago so you HAVE to leave work early on Tuesday to keep up with your chosen family. One drink, three rounds, lots of shouting answers in the form of a question. Every week another chance to redeem yourself or mock your friends. It's magic.” — Dan N.
- Karaoke at Sidekick’s
- Karaoke at Hidden Cove
- 4 a.m. bars
- Closing down the Owl (yikes)
- Photo booths in bars
- “Putting $20 into the jukebox at Old Town Ale House (best jukebox in the US, in my humble opinion) and checking out the latest NSFW paintings from Bruce Elliott." — Wil F.
- "Loud music coming out car windows (because it's usually good)" — Michelle N.
- “Old school bars at the crib.” — Jacoby C.
- House Parties
- "PARTY TROLLEYS specifically day time party trolleys" — Caroline Patton, City Cast marketing director
- Spotting a bunch of drunk people on a trolley
- Bike carts with crazy lights, music, tourists having a blast
- Navy Pier
- Fireworks at Navy Pier
- Ferris wheel at Navy Pier
- Centennial Wheel
- “The lake, summer, food scene, and House music. The Chosen Few!” — Xandrea R.
- Block Parties
- “In the summer when you can just stumble upon a street festival and your whole day takes a turn.” — Olivia T.
- African/Caribbean International Festival of Life
- Jeff Fest
- Chicago Humanities Festival
- Printers Row Lit Fest
- Chinatown Summer Fair
- Our lax livestock laws
- “My neighborhood rooster!” — Giselle V.
- How the city is never quiet
- The radio birthday song
- “Being on set for a Chicago show or commercial shoot.” — Jacoby C.
- Seeing random shows being filmed
- "Watching couples take wedding photos at Board of Trade, cancer garden, Garfield Park Conservatory." — Sidney M.
- "The Archdiocese of Chicago because of my parish and high school." — Bob Z.
- “The random churches in neighborhoods and if you’re lucky, when the churches ring on the hour. A free community timekeeper!” — Giselle V.
- When new baby animals at the zoo or aquarium get a naming competition
- The possibility of seeing all four seasons in one month
- “Watching the seasons change around the city.” — Kirsten & Absa B.
- Watching a winter storm from your cozy home
- Dibs
- “No matter where you are in the city, you seem to never be more than 100 feet from an old mattress leaning against an outside wall. Fanciest street, grittiest street, just look and find that mattress. It's very cool.” — Dan N.
- Finding cool furniture in the alley and taking it home
- Saying hi to dogs when walking around the city
- There is a book club for everyone
- “The Chicago Public Library! It’s part of every neighborhood and open to everyone. Its importance cannot be overstated!” — Liz L.
- Libraries (Harold Washington, Blackstone, Legler, Chinatown)
- The Bezazian Branch of CPL
- Chicago Bee Library
- Carter G Woodson Library
- Summer reading challenge at Chicago Public Library
- CPL’s children’s programming
- Cookbook clubs at the library
- “The Chicago Library's ebook collection. Keeps me company on the train!” —Liza M.
- "Always so much to explore — You could spend a lifetime here and never run out of things to discover." — Sidney M.
- “It’s easy to experience something new every day if you wish. Chicago has so many different places, activities, etc.” — Linda M.
- “EVERYTHING.” — Suzanne S.
Finding food from anywhere in the world
- “The diversity and abundance of cuisines in Chicago. Recent social media trends show an overabundance of “best of” lists and rankings of different foods/restaurants. I believe that this is a big enough city with room for everyone; each restaurant/establishment has something to offer. Not everything has to be ‘the best.’ There is something for everyone all across the city.” — Julio L.
- Eating around the city with 77 Flavors of Chicago
- Taipei Cafe
- Miss Saigon
- “Ramen-san's Express Lunch.”
- “Pueblito Viejo on Lincoln! (Super OG Colombian spot)” — Giselle V.
- The prices at Ghareeb Nawaz
- “Sinhá restaurant at 2018 W Adams St!” — Kate S.
- Nita’s Gumbo
- Mr. D’s Shish-Kabobs
- All of the amazing Caribbean food and Chicago’s love for Jerk food
- Demera
- “I love Bruna's in the Heart of Chicago off of Western. My family has been going for decades. The owner Luciano walks around to each table with a glass of wine in his hand.” — Lizzie
- Happy Lamb
- "All the kinds of fusion restaurants we have." — Michelle N.
- Asian Cuisine Express' Monday dollar tacos
- Hidden restaurants … like Oasis Cafe in Jewelers Row
- “I love the hole-in-the-wall restaurants, and how it can be a coin toss between food poisoning and the best restaurant you’ve ever eaten at.” —Eric R.
- We have a LOT of great Mexican food
- Peke’s Pozole
- Gorditas la Tia
- Carnitas Uruapan
- Birrieria Zaragoza
- Paco’s Tacos
- Late-night Atotonilco tacos
- Taqueria Los Comales
- Elotero carts in the summer
- La Michoacana
- Running into The Tamale Guy
- Taco trucks/carts
- “Tacos from the back of a grocery store.” — Lisa F.
- "Ethnic grocery stores where you can find A N Y T H I N G." — Simone A.
- Joong Boo Market
- Gangnam Market
- Gene’s Sausage Shop and Deli
- Patel Brothers
- Old World Market
- We have the best sandwiches
- Papa Cache’s steak jibarito
- La Sandwichera
- “Fresh Mozz sandwich from Medici on 57th.” — Kate S.
- “The Kali Mist sub from Cheba Hut in Lakeview!” — Carson M.
- Mr. Beef's Italian beef sandwich
- “The Mr. G sub (with giardiniera) from JP Graziano's — and the man himself, Jimmy Graziano.” — Lawrence B.
- Actually … giardiniera on everything
- The Chicago hot dog
- Dan’s Hot Dogs
- Getting roasted at the Weiner's Circle
- Home Depot Polish
- Maxwell Street Polish
- Late-night Maxwell’s trip
- Cheap, late-night hot dog or burger from Red Hot Ranch
- Getting a Big Baby
- Cheezborgers at the Billy Goat
- Giant
- Patty Please smash burger at Small Bar
- “Leavitt Street Tavern burger being arguably the best in the city (Michelle would back me up on this one).” — Sidney M.
- “The $20 burger, beer, and shot special at Leavitt Inn and Tavern.” — Michelle N.
- Having TWO iconic types of pizza
- Tavern-style pizza (“We just called it thin-crust in my day.” — Bob Z., City Cast Chicago senior account executive)
- True tavern-style pizza at Vito & Nick’s
- Middle Brow's Tavern-style Tuesdays
- Phil’s Pizza on 35th
- "Learning that D'Agostinos has pizza that is half-off on Wednesdays 🤓" — Sidney M.
- Fox’s Pub pizza
- “JB Alberto's slinging slices (and whole pies) at Northside bars!” — Mara J.
- Italian Fiesta
- "Waiting 2 hours for Pequod’s and only kind of regretting it." — Wil F.
- “The Whale in Logan Square.” — Maggie S.
- “Sunday Roast at Hawksmoor!” — Tricia G.
- "Old-school Chicago restaurants like Lou Mitchell's and Manny's Deli that have become institutions." — Sidney M.
- Portillo's chopped salad
- "Chicago's commitment to combining foods and bevs in ways that don't make sense (e.g., Italian beef pizza, beer-flavored pizza, caramel popcorn beer, cbd giardiniera)." — Sidney M.
- Chicago soul food
- All of chef Erick Williams’ spots (Virtue, Daisies, Mustard Seed, etc.)
- BBQ from I-57, Lem’s, Sanders
- “So many options for great ribs and chicken.” — Katie W.
- No Sauce Az Smokehouse
- Ribs at Twin Anchors
- Rib tips Jay’s Backyard BBQ
- “The Sportsman Summer BBQ Series.” —Emily C.
- Cane’s on Michigan Avenue
- Chicken sandwich from Big Boss Fried Chicken
- Large fried shrimp from Lawrence’s Fish and Shrimp
- Food Allegiances
- Uncle Remus
- Harold’s (But the right location)
- Extra mild sauce
- Best Intentions honey mustard
- Grabbing a fresh loaf of sourdough and a rotisserie chicken from Totto’s Market
- “Oakley Foods and all neighborhood corner stores who really know the community members.” — Jacoby C.
- “Walking to your neighborhood corner store for munchies!” — Giselle V.
- Pizza puffs
- Garrett Popcorn, the Chicago mix
- Cracker Jack
- Flamin’ hots and cheese with meat and peppers
- Richard’s Super Premium Ice Cream
- Italian ice
- First visit to Kilwins
- Rainbow Cone
- Margie’s root beer float
- Old Fashioned Donuts
- Paczki
- “Defloured gluten-free bakery in Andersonville is my favorite place for gluten, dairy free, and/or vegan treats! They have so many creative options, and there's something new to try every time I go, and it's all excellent!” — Liza M.
- Borinken Cakes
- Caramel Peach Pie from Justice of the Pies
- Brown Sugar Bakery
- Cadinho Bakery and Cafe
- Racine Bakery
- La Central Bakery
- Mindy's Bakery
- "The incredible selection of gummies at O'Hare Airport (fave: peach penguins)" — Andi M., City Cast chief creative officer
- Fannie May Candy
- Tootsie Roll
- King Sweets
- Peppermint pickles
- “Chicago summers as a kid going to candy houses or neighborhood homes that were candy stores! Cheaper than the grocery stores and those who ran them felt like family." — Mariah M.
- Brunch at m.henry
- L&G
- Batter & Berries
- Cafe Moustache
- Goddess & the Baker
- Kusanya Cafe
- Sip & Savor
- 7323 Chicago Cafe
- Robust Coffee Lounge’s breakfast sammie
- Neighborhood bars on nearly every corner
- Big Chicks/Tweet
- “Turner Haus Brewery” —Talibah F.
- The Globe Pub
- Palomas at Osito’s Tap
- Maria’s Packaged Goods and Community Bar
- Free shot at midnight at Punch House
- West Loop bar crawl
- Cara Cara Club
- Grabbing a drink at the Zachary
- Drinks and pool at Chris’s Billiards
- "Sitting in Al Capone's booth at the Green Mill ... Sitting anywhere at the Green Mill" — Wil F.
- Real speakeasies
- Bartenders who make you off-menu drinks
- Heavy-pour spots (Ceres, Cookie’s, Go Tavern)
- “Drinking glogg at Simon's Tavern.” — Jan V.
- “The dive bars!” — Tricia G.
- Cheap drinks
- Uptown Lounge
- “A good Avondale happy hour.” — Kate R.
- All the local breweries
- Revolution Brewing
- Open Outcry Brewing
- Monochrome Brewing
- Green Line by Goose Island
- Restaurant Week
- “Your local restaurants knowing you and your order.” — Michelle N.
- "The TikTok guy eating his way through every country in the world at Chicagoland restaurants." — Sidney M.
- “Dennis Lee's substacks (The Party Cut, Food Is Stupid): One is a thoughtful, down-to-earth celebration of Chicago's small but mighty restaurants, and the other is ... a truly creative endeavor.” — Nathalie R.
- New restaurants opening all the time
- “No matter where you go, the food will be good.” — Michelle N.
- The fact that we didn’t mention Malort on this list …
- … except we kinda just did.
“If I’m out of town and I hear someone speak a certain way I think to myself ‘They might be from the crib.’” — Brandon P.
- People who say “West Side, best side” or “290, baby”
- "The way Chicagoans are cocky-humble. We don't talk that much about how we're the best at things because we just KNOW we are." — Simone A.
- Adding an s to the end of things (Jewels)
- Putting things 'on' other things (on my mama, on my dead granny, on my kids)
- “I love that when you run into another CPS kid as an adult, we all still have opinions on where each other went to high school. School pride runs very deep.” — Anna
- People who went to Jones and talk about Chance the Rapper.
- "People who went to Whitney Young and talk about Michelle Obama." — Sidney M. (Whitney Young grad)
- "People who identify where they live/grew up by their Parish (Q: Where are you from? A: St. Barnabas).” — Bob Z.
- "We’re from the state of Chicago!" — Mariah M.
- Saying you are going "down south," "up north," or "out west"
- Neighborhood names or area nicknames. (e.g. K town, La Villita, The Gardens)
- "The specific Chicago pronunciation of ‘viaduct.’" — Simone A.
- “Da Bears!” — Manuel M.
- Using the word “shorty”
- Calling people “goofy”
- Calling people “goofies”
- The term "jagoff"
- “Talking shit.” — Michelle N.
- "Telling people what ‘The Bear’ gets wrong about Chicago.” — Wil F., City Cast content director
- “The Wilson Ave Water Crib google maps reviews.” — Jessica H.
- "People are really proud to be from Chicago! And Chicagoans are good at telling people they're from Chicago." — Sidney M.
- The accents
- "Blend northern and southern accents." — Jacoby C.
- "Going ‘Just survive the winter g’ and ‘Summers are worth it’" — Jacoby C.
- The phrase “extra mild sauce please"
- "I do love Ope even though it’s more midwestern!!" — Caroline P.
- "Languages! Hearing all kinds of languages at any given time." — Simone A.
The art
- "All my reflections on the 'Bean'" — Michelle N.
- “The ‘Bean’ by night.” — Roberta F.
- “The Helping Hand Sculpture of Palmer Square” — Miguel
- “The Light of Truth” Ida B. Wells National Monument
- “Fountain of Time” in Washington Park
- Keith Haring statue at AIDS Garden Chicago
- Oz Park statues
- “Sh*t Fountain”
- “Creative ways to get people to pick up their dog poop (e.g., sh*t fountain, no poop fairy merch from park district).” — Sidney M.
- Good graffiti
- "Great Wall of Chicago" mural
- Back of the Yards Video Game mural
- Murals by Emmy Star Brown
- Branch Library mural
- Hebru Brantley murals
- Loyola Sea Wall
- Rogers Park Mile of Murals
- Stony Island murals
- Viaduct murals at 46th and Archer
- 18th Street murals
- National Museum of Mexican Art
- Ukrainian Institute of Modern Art
- National Museum of Puerto Rican Arts and Culture
- Small storefront or house museums
- Free museum days
- Free Thursday entry at the Art Institute
- Museum of Contemporary Art
- South Side Community Arts Center
- Pilsen Art and Community House
- SkyART
- Jackson Junge Gallery
- Cherry Mountain Arts Gallery
- Made Gallery
- Buena Vista Project
- Englewood Arts Collective
- Sinag
- Stony Island Arts Bank
- The Fleurotica fashion show at Garfield Park Conservatory
- The film and TV community!
- “Southeast: A City Within a City”
- “Music Box Theatre” — Liz L.
- Singalongs at Music Box
- Gene Siskel Film Center
- Destinos
- Chicago International Film Festival
- So many film fests (Doc10, Reeling, Black Harvest)
- “The super cool (short) film fests like Black Harvest, Doc10, Black Alphabet, Screen Time and Big Shoulders.” — Jermaine Thomas II, City Cast marketing manager
- Rooftop Cinema Club
- Chitown Movies Drive-In
- “Chicago theaters.” — Kevin S.
- How we’re the backdrop for so many iconic movies
- “The Fugitive”
- “Blues Brothers”
- “Candyman”
- “Ferris Bueller’s Day Off”
- And we’re especially good for rom-coms
- “Love Jones”
- “While You Were Sleeping”
- “All the amazing theatre we have!” — Emma T.
- Chicago Theatre Marquee
- Seeing all the dope Chicago actors at the Goodman
- “Broadway in Chicago 5-show package is a good deal!!” — Sidney M.
- Court Theatre
- TimeLine Theatre
- Belmont Theater District
- Aguijón Theater Company
- Experimental theater (Neo-Futurists, Puppet Lab, Hot Clowns)
- “The Chicago International Puppet Theater Festival.” — Liam G.
- “The many storefront theaters!” — Kate T.
- Storefront theater festivals
- Intimate shows in a basement, living room, or wherever.
- “I love the performing arts community here. I feel like if I were in NYC or L.A., I might get lost in the shuffle. Chicago has a thriving scene for every experience level.” — Anna V.
- Spoken word/poetry
- Luya Poetry
- Kumba Lynx
- Big Kids Show
- Chicago's storytelling and live lit scene (Grown folks stories, Karaoke storytellers, the moth, Storylab, Write Club)
- "Seeing Jacoby perform IRL! (He is so talented!)" — Sidney M.
- Local variety shows (Welcome to The Show, Not That Late Show, The Armando)
- Kherein Center for the Arts
- Mayfair Arts Center
- Logan Center for the Arts
- The comedy scene
- Unique comedy/improv shows
- "Lisa Beasley's comedy show at the Laugh Factory (shoutout Lory Litefoot, shoutout corporate Erin)" — Sidney M.
- The live music scene
- "Underground music scene — concerts under bridges, raves on trains, shows on top of the Weiner’s Circle hot dog restaurant." — Tim H.
- "All the great music from Kingston Mines to The Riviera to Green Mill to Soldier Field." — Bob Z.
- Le Piano
- “The Old Town School of Folk Music.” — Peter X.
- “Old Town School of Folk Music's Instrument Petting Zoo.” — R.A.
- “The Thursday concerts at the Taste of Chicago in Grant Park, specifically the feeling of everyone singing and dancing together enjoying themselves with the skyline in the background.” — Viviana O.
- Boiler Room at Grant Park
- “Concerts at Northerly Island.” — Bianca P.
- Catching the best concerts and picnics with friends at Millennium Park concerts
- Wandering into Dorian's any night and catching the best local musicians
- Concerts at Wrigley Field
- Live jazz on a train platform
- Englewood Jazz Festival
- Chicago Show Calendar
- The Riviera
- Aragon Ballroom
- House Music
- “Soul Liberation: A Frankie Knuckles House Music Celebration”
- Noche de Cumbia with Eva Maria
- Late night radio DJ mixes
- “Acid Rap” mixtape
- Jamila Woods' "Boomerang"
- "La Noche Que Chicago se Murió" by Banda Toro
- Wendell Phillips Academy alumni — Sam Cooke, Nat King Cole, Dinah Washington, Herbie Hancock, Marla Gibbs, Vivian Harsh
- Femdot’s mechanical pencil
- “J Bambii’s fifis.” — Jacoby C.
- “Food & Liquor” by Lupe Fiasco
- Mick Jenkins’ whole discography
- Seeing Asha Omega and Achillez at the Ramova
- “Just Relax” by King Louie
- Drill music
- Footwork
- Steppin’
- Casper Slide
- DLow Shuffle
- Wopping
- “Katie Got Bandz” dance
- “The pole dancing community! Especially Pole Icons, Brass Ring and Pole Night at Provocateur.” — Mollie W.
- Fly Honeys
- Deeply Rooted Dance
- Muntu Dance
- M.A.D.D. Rhythms
- “Can You Hear Us Now? The Queer Tap Dance Revolution”
- “I love the summer art fairs, festivals and especially the Chosen Few picnic.” — Connie F.
- Jewelry at farmers markets
- “Tonika Lewis Johnson's interesting and thoughtful art projects/installations that inspire other Chicagoans' to evaluate their relationships to other parts of the city.” — Sidney M.
- “Mortal Kombat”
"My fellow die-hard Chicago sports fans." — Bob Z.
- All the sports championships
- Candace Parker coming home to lead the Sky to a chip
- Kahleah Copper's finals MVP
- "Good at reliving the glory days — still talking about the Jordan days 20 years later and the '85 Bears." — Sidney M.
- 90s Bulls conversations.
- Madhouse on Madison
- Seeing MJ play at the Madhouse on Madison
- Fans clinging to 90s Bulls
- Beginning of Bulls game/ iconic theme song
- All of the banners at the UC
- D-Rose highlights
- Simeon's basketball legacy
- High School sports rivalries
- Kenwood Lady Broncos winning their first basketball state title
- Mount Carmel’s football legacy
- Gately Stadium
- All the cheer teams and marching bands around the city
- “H.S. Sports, especially football in the Catholic League.” — Bob Z.
- Devin Hester highlights
- Devin Hester’s Superbowl return
- Family days during Bears pre-season
- "Bringing cardboard to Bears games to put under your feet to help keep them warm when Soldier Field has snow." — Bob Z.
- Bears Fight Song, “Bear down, Chicago Bears"
- Bears fans' unyielding optimism
- Packers vs. Bears at Soldier Field
- “The walk to the Bears game and the ‘F the Packers’ cheers.” — Noell N.
- “The walk from The Roosevelt stop to Soldier Field for a Chicago Fire or Bears game.” — Kyle J.
- Big Ten fans and designated school/team bars
- The Sox Logo
- 35th & Shields
- Sox game pre-gaming
- “Downing a beer on the walk from parking lot G to Comiskey.” — Jacoby C.
- White Sox helmet ice cream and nacho helmet
- Fireworks at Sox stadium
- White Sox games in old Comiskey
- Na, Na, Na, Na … Na, Na, Na, Na … Hey, Hey, Hey … Goodbye!!!!
- Harry Caray pitching Falstaff beer when he was the Sox announcer
- Sox 2005 World Series win
- "How the city came together to root for the Sox to lose [in 2024] because there was just no hope, and it was more iconic anyway." — Sidney M.
- Crosstown Classic
- The Cubs
- “Loved getting to be my friend's plus-1 at a work event that entailed free food in a suite at Wrigley.” — Sidney M.
- Cubs 2016 World Series Win
- Statues outside of Wrigley Field
- The seats on top of the buildings next to Wrigley
- Home run fireworks
- When the Blackhawks kept winning
- The National Anthem at Hawks games
- Stars and Fire games
- When they play Chicago artists at Fire games
- Mascots: Benny, Staley, Tommy, Clark, Southpaw, etc.
- "Chicagoland weirdly being a mascot epicenter (e.g., created the pop-tart mascots, the former mascot hall of fame being in NW Indiana until recently)" — Sidney M.
- Chicago little league baseball
- "16-inch softball, no gloves, the Clincher" — Bob Z.
- Mt. Greenwood softball games
- "When Mexico's national soccer team plays at Soldier Field." — Michelle N.
- WWE events at Allstate Arena
- “My gym Chicago Strength 🫶” — Kate R.
- “The best and biggest cyclocross community in the nation.” — Michael Y.
- "Empowering generationally bad sports ownership." — Jacoby C.
“Its history.” — Laurie K.
- Reversing the river
- The defense of Mrs. O’Leary’s cow.
- How everything is related to the 1893 World's Fair
- The story of raising the city from the mud
- Union Stockyards Gate
- Noble-Seymour-Crippen House
- History of Illinois’ 1st Congressional district
- The roots of improv
- Chicago Defender history
- The eclectic design of the Ebony Test Kitchen
- “I love how Chicago has been the capital of so many industries throughout history — from railroads to meatpacking, it makes the city that much more interesting” — Sidney M.
- History of mail order retail
- “Our history of radical activism.” — Viral M.
- “The history of the Pullman porters in establishing the labor and civil rights movement.” — Jason H.
- Dr. Daniel Hale Williams performing first successful open heart surgery on the south side
- Legacy Walk in Northalsted
- Humboldt Walk of Fame
- Basically casting SNL for the past 50 years
- “I love Downtown, the Willis Tower that used to be called Sears Tower.” — Melissa C.
- “Old St. Pat’s.” — Bob Z.
- “The storied history of Parkway Gardens.” — Jacoby C.
- "The happy-sads/growing pains of watching the city change in a lifetime." — Sidney M.
- Turtle Races at Deja Vu on Clark and Wrightwood
- Old Maggie Daley Park
- Chicago park district camp memories
- “Collecting lightning bugs in the summer with my cousins when we were little.” —Giselle V.
- Listening to the radio early in the morning to hear if we had a snow day.
- “The toboggan run at the Dan Ryan Woods. No longer there.” — Bob Z.
- “Watching my mom buy the Tribune and Sun-Times papers from the man in the middle of the street on the way to school.” — Jacoby C.
- Ford City Mall in 1999
- “Being a 90s baby from the South Side (60628!!!)” — Jae B.
- Back-to-school shopping at the old Old Navy on State Street
- "Commercials! wtf were they on with eagleman?" — Sidney M.
- Old school jingles (Empire, Moo & Oink, Andriana Furs)
- "Getting free samples at Ghirardelli, Hershey's, Yogurtland, and Forever Yogurt in Gold Coast/Mag Mile area in middle school." — Sidney M.
- That the “wear sunscreen” speech originated in Chicago
- “Seeing the universal soul circus for the first time." — Jacoby C.
- "Learning to use a DSLR camera and take photos around Chicago with After School Matters." — Sidney M.
- "The summer "Transformers 4" was filmed in Chicago — was really geeked about it" — Sidney M.
- "Going to the Chicago History Museum for the first time as a kid" — Michelle N.
- Field trips to museum campus
- Field trips to the Field
- Sue the T. Rex
- "Going to the museums with my Aunt." — Bob Z.
- "Hanging out at the Adler's Doane Observatory for a summer." — Sidney M.
- Field trips to the zoo
- The old McCuddy's across from Comiskey Park
- "Watching my cousin have a DIY wedding at Chicago Industrial Arts & Design Center." — Sidney M.
- “Watching my dad recreate his proposal to my mom on the steps outside of the Art Institute on their 10-year wedding anniversary." — Sidney M.
- Shopping at Water Tower
- Going downtown with friends after school just because and without adult supervision
- Going to Oak Street Beach with your friends on the last days of school
- Basement parties in high school
- Pilsen bar crawl when you turn 21
- "Watching the 'Fifth Element' while sitting at the bar at Simone's." — Simone A.
- Party buses stopping at the old rock and roll McDonald’s.
- The Pokemon Go crowds at Pratt Beach
- Frozen pants dibs
- “Winning last-minute rush tickets to the Hamilton lottery after applying for months.” — Sidney M.
- This one TikTok from 2022
- That one time Val Warner appeared in “South Side.” We really miss “South Side.”
- Taylor Swift Eras Tour at Soldier Field June 4, 2023
- "I moved here due to an internship in college and had never been here before. I was fresh off a traumatic break up and was walking to my dream job after getting off the L. ‘Green Light’ by Lorde came on my headphones and it was the first time I ever felt true independence!!!!!! Love this city for giving me that experience." — Caroline P.
- "I'll say it: Rat Hole and all its accompanying hype." — Simone A.
“Better public transportation than in most major cities” — Jordan S.
- CTA Express Buses
- The 50 Damen Bus
- Elevated Trains
- “Riding the L through all the neighborhoods and seeing everyone's backyards.” — Rebecca J.
- CTA heat lamps
- “Catching up with my local CTA station attendant.” — Michelle N.
- “The Chicagoans threw a farewell party to Jane Martin, customer service representative at the Armitage Brown Line station.” — Ava Wojnowski, City Cast on-call newsletter editor.
- “Getting the private seat in the back part of a CTA train car, especially when it’s the last car on the train. One of the coolest/most unique views on the CTA.” — Max K.
- The new Wilson Red Line stop
- Seeing the sunset from the Red Line
- Views from the Pink Line
- Views from the Green Line
- “Seeing the Orange Line train pass by from my living room windows.” — Michelle N.
- “Taking the Brown Line over the Chicago River in the Loop.” — Liv K.
- “Watching Red and Purple line trains go by at night while waiting at the Diversey Brown Line stop.” — Jamie T.
- Being left behind by the last Purple Line train
- When the CTA is on time
- Rock Island Metra ("aka the two-beer Metra" — Mac)
- "The commuter lines to get out of the city are perfect!! Just used the south shore line to go to Michigan City for the weekend." — Caroline P.
- “Taking the IC to downtown from the south suburbs and the groups who always sat in the same 4-seater every day.” — Bob Z.
- “Public transit's affordability.” — R.A.
- That our transit takes tap-to-pay
- The lack of hills
- “Walk-ability” — Bethany M.
- “Walkable restaurants, bars, libraries, and community hubs.” — Michelle N.
- Divvy on the lakeshore
- “The grid. It makes sense and it’s easy to navigate. Plus, you can learn the hundreds (e.g. Roosevelt is 1200 south, Halsted is 800 west) and suddenly addresses become legible and simple to find!” — Liz L.
- The same street will take you to the other side of the city
- “Ending up at an intersection I've never even seen before.” — Simone A.
- "Everyone agreeing the 79th Street (Stony Island) intersection is hell on earth" — Jacoby C.
- Pulling out into the intersection to wait for a left turn
- “People that know how to parallel park.” — Kyle J.
- Walking on the expressway during a caravan
- Hearing WBEZ, WGCI, or 92.3 in the Uber or Lyft
- Riding down DLSD through the Loop, skyline on one side, Lake Michigan on the other.
- “Summer night drives on LSD.” — R.A.
- Reminding out-of-towners that LSD doesn’t mean acid
- Lower Wacker as a quick way to get through downtown traffic
- The Pedway
- That feeling when a road or path has finally been repaved
- “Chicagoans are actually decent drivers in the snow.” — Simone A.
- Route 66 starts and ends in Chicago
- Water taxi to Chinatown
- Water taxi to Michigan Avenue
- “Electric boat rentals to easily explore the river — amazing on a warm summer day!” — Emily C.
- Getting boats together in the Playpen
- Two airports
- It's easy to book a flight to anywhere or from anywhere in the world
- “It's easy to get to the east or west coast!” — Amy M.
- “Harry Caray's in Midway! Best airport bar ever." — Caroline P.
- “O'Hare -— great airport for finding things to do on long layovers.” — Lizzie G., City Cast roving producer
- O’Hare’s neon light tunnel
- Neon light tunnel from Terminal 1 to Terminal 2 at O’Hare
- "Recreating the airport scene from ‘Home Alone’ every time I’m in O'Hare" — Wil F.
- “Knowing someone loves you when they offer to pick you up or drop you off at O'Hare.” — Michelle N.
- "Manipulating folks into taking their friends to Midway because ‘at least it’s not O’Hare’ and vice versa." — Jacoby C.
The way we’re built.
- “The skyline!” — Tricia G.
- Seeing the skyline from different POVs (from Edgewater, the Adler, Promontory Point, Indiana Dunes, 87th st Red Line stop)
- “Awesome skyline.” — Susan M.
- “Alleys … Chilling out there, playing basketball — I just think that alleys are really important to the Chicago lifestyle.” — Corli Jay, The Triibe reporter
- Keeping trash in the alleys
- “Alleys and the underground streets. It keeps our city clean vs. the garbage at the curb you see in NYC.” — Bob Z.
- Gangways
- Back patios
- Back porch furniture
- Walkups and back steps
- Sub-basements with wood paneling
- Chicago bungalow
- Greystones
- Terra cotta buildings
- Courtyard buildings
- “Walking my dogs around Ukrainian Village enjoying all the different style homes. From bungalows, worker cottages, three flats and apartments. Heading east on Augusta, beautiful view of downtown.” — Gina M.
- The perpetual orange glow from our streetlights
- Being in a skyscraper city and still seeing the sky
- “Returning from a road trip heading north on the Dan Ryan, or flying over the lake into O'Hare, and seeing the skyline of America's most beautiful city.” — Ann A.
- “The spark of joy that hits when you catch a glimpse of the Sears Tower beckoning to you in the distance, even when you're somewhere out in the burbs.” — Lawrence B.
- Your first time at the Ledge at Sears Tower
- "Sitting on the grass next to the Shedd Aquarium to look at the skyline on summer nights." — Michelle N.
- “The view from Museum Campus.” — Cristina B.
- Old architecture
- "Being able to recognize buildings in old photos" — Simone A.
- “Seeing buildings from every era, old and new.” — Kyle B.
- The Wrigley Building
- “Magnificent Mile” — Cherita W.
- The Standard Club building
- St. Regis Hotel
- Harold Washington Cultural Center
- The Chicago Cultural Center
- Chicago Cultural Center Tiffany Dome
- Carbon and Carbide building
- “The face-less statue on top of the Board of Trade.” — Sidney M.
- Movable bridges (“37 = most in North America & second most in world” — Jacoby C.)
- Michigan Ave Bridge
- Raised bridges
- Neighborhood name signs/arches
- Neighborhood commercial districts
- “There's an Old National Bank billboard on Ashland near the Clybourn Metra platform, that always has ads with silly puns and jokes of varying relevance to the business. They're not very good jokes, but they make me smile. I wonder who writes them?” — Liza M.
- South Shore Cultural Center and Nature Sanctuary
- Art Deco outside of downtown
- The castle in Beverly
- Ceiling inside the Aragon Theater
- "Various church architecture." — Jacoby C.
- Chicago Architecture Center
- Architecture boat tour
- “Open House Chicago giving everyone a chance to explore so many new spots.” — Sidney M.
Getting recognized by your local businesses
- Beverly Records
- Pullman Farmers Market
- Gotham Greens
- Bookie’s
- 95th Street Farmer’s Market
- Bronzeville Children’s Museum
- House of Music
- St. Leo’s Residence for Veterans
- Peaches’ Boutique
- The Quarry
- Pen and Paper: A Joint Creative
- R.A.G.E. Englewood
- P.E.A.C.E Campus
- Englewood Branded
- Johnny Twist Blues Museum
- “The Grow Greater Englewood farm on 58th and Halsted” — Elizabeth A.
- 57th Street Books
- DuSable Black History Museum and Education Center
- Miyagi Records
- Boxville
- Powell’s Books
- First Aid Comics
- Hyde Park Records
- Silverroom
- South Side pitch competition
- Call & Response Books
- Super Mall
- Maribis Cannabis Dispensary
- "Going to Zap Props and the Economy Shop to thrift weird props for high school plays." — Sidney M.
- Bridgeport Records
- Freestyle Ceramics and Tufting
- Artesanias Elena
- Principle Barbers
- Sound baths at El Paseo Garden
- Pilsen butterfly sanctuary
- Mestiza
- 606 Records
- Venados Running Club
- Pilsen Community Books
- Mercado de Colores
- The Resurrection Project
- Pinwheel Records
- North Lawndale Employment Network
- Out of the Past Records
- “Sew Anastasia’s Sewing Studio” — Anna J.
- Sprout Home classes
- Austin Town Hall Farmers Market
- “Chicago Modern Quilt Guild” — Anna J.
- Madison Street Books
- South Asia Institute
- Sandmeyer’s Bookstore
- Exile in Bookvilee
- Daley Plaza Food Truck Fridays
- American Writers Museum
- After-Words Bookstore
- Shuga Records
- Volumes Bookcafe
- Myopic Books
- Quimby’s
- Lily’s Record Shop
- Los Amigos Books
- Green City Market
- Judy Istock Butterfly Haven at Peggy Notebaert Nature Museum
- One Tail at a Time
- “Friends of the River clean-up day!” — Anne P.
- “Logan Square Mutual Aid” — Miguel
- “Whaddayaknow Free Pub Trivia! I love how easy they make it to find events anywhere in the city any day of the week. Specific shout out to Music Trivia on Mondays and Music Bingo on Tuesdays, both at AliveOne with host Bryson.” — Kate S.
- Gramaphone Records
- Bucket O’ Blood Books and Records
- Roscoe Books
- Waveland Bowl
- The Last Chapter
- Three Avenues Bookshop
- Reckless Records
- Dark Tower Comics
- Bric-a-Brac Records
- Record Breakers
- Rolling Stones
- “Harebrained (their Chicago design collection)” — Bethany M.
- Bob’s Blues and Jazz Mart
- Haymarket House and Haymarket Books
- Respair Media
- Tone Deaf Records
- First Nations Garden
- Muslim Community Center
- “Forteza Fitness in Ravenswood, where you can learn real swordfighting and medieval combat! The nerdiest type of gym.” — Liza M.
- Rev Billy’s Chop Shop
- Interstellar Space
- Lincoln Square Farmers Market
- Laurie’s Planet of Sound
- Merz Apothecary
- Round Trip Records
- “Esquire Barber Shop” — Alex T.
- Uncharted Books
- “I love all the speakeasies. My fav, Chicago Magic Lounge.” — Lindsay S.
- “Unabridged and Women and Children First bookstores. Both have extensive queer (and queer romance) sections, the feminist sci-fi and fantasy, and great staff recommendations in every genre. I never fail to find several wonderful books every time I visit!” — Liza M.
- “The Andersonville Galleria” — Liza M.
- AlleyCat Comics
- Rattleback Records
- Third Coast Comics
- Electric Jungle
- Sunflower City
- Ladies Who Lit book club
- Noname’s book club
- Silent book clubs
- Read & Run Chicago
- Chingonas Run Chicago
- Latina Sweat Project
- “Chicago Sews” — Anna J.
- Our diverse, active, and strong local media scene!
- The Triibe
- Chicago Reader’s Best of Chicago
- South Side Weekly’s Best of the South Side
- Injustice Watch's Judicial Guide
- … and City Cast Chicago and Hey Chicago (obviously)
When Wrigleyville bars go all out for the holidays
- The seasonal lawn ornament displays at the Hermann Weinhardt House (“I’m not just talking Halloween and Christmas — think graduation season! Think Oktoberfest! And that’s not even mentioning the incredible, colorful, ornate, gingerbread-esque architecture of the mansion itself.” — Kate S.)
- Patio season lasting into the fall
- Chief O’Neill’s for St. Paddy’s Day
- Green river around St. Paddy’s Day
- “Going to see the Chicago River dyed green.” — Kevin S.
- “Indie Bookstore Day in Chi is underrated and more people should go and do the crawl!” — Sidney M.
- Juneteenth Family Festival
- Air & Water Show
- Mexican Independence Day caravans
- Mexican Independence parade
- Apple Fest
- “Halloween in Gold Coast.” — Cristina B.
- "How seriously everyone takes Halloween — come October, people are outnumbered by skeletons." — Andi M.
- Christmas tree shopping at Ivy's
- “How for the Christmas Holidays everything lights up from neighborhoods, to houses, to the smiles, and the shopping!” — Melissa C.
- Holiday lights downtown
- Walking down Michigan Ave during the holiday season
- “Going to see Santa at Macy's and lunch at the Walnut Room with family.” — Noelle N.
- “93.9 LITE FM Christmas music 24/7 for months leading up to the holiday” — Sidney M.
- Christmas decorations at O'Hare
- Neighborhood Christmas trees, toy drives, and holiday food giveaways
- New Year’s at the Riverwalk
Enjoying the outdoors, even in a big city.
- Grant Park
- Buckingham Fountain at 10 p.m. when they turn on the classical music
- Sir Georg Solti Garden
- Millennium Park
- Free music at the parks
- Movies in the Park
- Douglass Park mini golf
- Putt putt golf at Maggie Daley
- Maggie Daley Park play garden
- The wooden pirate ship at Maggie Daley Park
- “Ice skating on the ribbon.” — Ava W.
- Ice rinks in parks ("I got engaged on one. Yep, took a knee in rented figure skates." — Bob Z.)
- Garden of the Phoenix in Jackson Park
- Cherry Blossoms at Jackson Park
- Palmer Square Park
- Ping Tom Park
- Rogers Park
- Mary Bartleme Playground & Dog Park.
- Walking dogs at Lorraine Dixon Park
- “Watching the planes fly at sunset at Horner Park hill.” — Kate R.
- Burnham Nature Sanctuary
- Soccer games at Marquette Park
- Bike jumps at Big Marsh Park
- Columbus Park refectory and council ring
- Ashburn Prairie
- Hegewish Marsh Park
- Dan Ryan Woods
- Forest Glen Woods
- Budlong Woods
- All of the reclaimed green space
- Steelworkers Park
- Flower shows
- Garfield Park & Lincoln Park conservatory flower shows in the dead of winter
- “Spending time in the Alfred Caldwell Lily Pool, the historic garden located in Lincoln Park.” — Larry L.
- “Picnic in Lincoln Park.” — Sofia M.
- “Lincoln Park! Fountain Girl in Spring.” — Linda M.
- “The free zoo” — Jordan S.
- The conservatories (Lincoln Park and Garfield Park)
- Fairy houses at the Garfield Park Conservatory
- Lagoons (Auburn, Marquette, Humboldt, Columbus)
- “When the ponds freeze over at Humboldt Park.” — Kate R.
- The geese at the McKinley Park Lagoon
- “Montrose Point Bird Sanctuary, one of the best spots in the country for birdwatching yearround.” — Chris B.
- Riverwalk
- Kayaking the river
- Sunsets
- “Lake Michigan.” — Roberta F.
- Jumping into the lake on a hot summer day.
- Cold Plunging in Lake Michigan
- “Watching the sunrise while swimming in Lake Michigan.” —Kelly J.
- “Winter morning view of Lake Michigan as you drive south on DLSD. Gold morning light washing the buildings, the bare trees in silhouette dark against the water and sky blue with a band of snow running along the horizon.” — Dan N.
- Running along the lake
- “The Lakefront Trail!” — Tricia G.
- “Views from the South Side lakefront trail.” — Katie W.
- “Lakefront trail, specifically biking north around the curve at the Shedd and BOOM skyline 😍” — Courtney W.
- Riding bikes into the lake/river
- Our freshwater coast.
- Freshwater beaches
- Early morning lakefront workouts
- Concrete beaches
- “That beautiful day every Summer where the temperature is hot but not unbearable, you're sitting on the concrete steps at Montrose Beach with your friends, and there's a gentle breeze. The perfect Chicago Summer day to swim, nap, or just hang out.” —Brad K.
- All the great harbors along the lake.
- Oak Street Beach skyline and lake view
- "The gorgeous melting pot of people and dogs and scents and sounds that is Foster Beach." — Andi M.
- Loyola Beach
- Fire pits at the Point
- Rainbow Beach
- “Bongo Beach” — Imani K.
- “The sound of the seagulls in the summer.” — Giselle V.
- “I really do love the view of the lake and downtown from Lakeshore Drive in all seasons and times of day: sunrise, sunset, nighttime, summer, winter, cloudy, sunny — the way the water can be so many colors, gold and orange under the sunrise, a depth chart in shades of blue in the sunlight, silver when cloudy, green when a tornado's coming — waters gently rippling or crashing in a storm or slowly heaving ice onto the shore — fog wreathing the skyscrapers, like they pulled clouds out of the sky — the lights from the buildings at night, reflecting on the river, the ferris wheel at Navy Pier — every time we come back from a trip, that's how I know I'm home.” — Liza M.
- Calumet Park and Beach
- “The Bloomingdale Trail ("606"), particularly how it brings together four neighborhoods and people from all walks of life as well as the much-needed plant/nature along the trail.” — Quentin M.
- Major Taylor bike trail
- Black Joy Ride
- The Children's Garden at Morton Arboretum
- The smell of native plants
- "The smell of crushed mulberries on a Rogers Park sidewalk in summer" — Simone A.
- Fairy houses in yards and sidewalk planters
- The excitement as summer turns to fall
- Tree-lined streets in fall
- Fall foliage at parks
- “Hot take, but I love Chicago winters and think they're underrated. I love bundling up to walk along the frozen, snowy lakefront, and feeling like I'm in another world among the ice formations — then warming up at a cozy neighborhood spot.” — Mara J.
- Sledding down small snowy hills in local parks
- “Skitching. Grabbing the rear bumper of a car and getting pulled down the street on ice/snow.” —Bob Z.
- "The way the snow looks like glitter when it’s lightly snowing and it runs under a street lamp!!! Magical!!" — Caroline P.
- The Hawk
- Wearing multiple layers in the winter
- "Collections of outerwear. Need multiple jackets for every season." — Simone A.
- The excitement as winter turns to spring
- 5 p.m. sunsets as we come out of winter
- That first nice day after winter when everyone is out and about
- “That first warm day in the spring is lit! Everybody’s out and about!” — Vero
- “That first nice day of spring where everybody and their mother are outside eating, in a park, walking, and just savoring it.” — Ike W.
- That first warmish (aka 50 degrees and sunny) day in Chicago after weeks/months of cold winter weather.” — Carrie E.
- Tulips on Michigan Avenue in the spring
- “All of the tulips in the spring!” — Brianna W.
- The excitement as spring turns to summer
- Rosehill Cemetery
- Oak Woods Cemetery
- Graceland Cemetery
- “The Graceland Cemetery coyotes … to love them is to keep your distance!” — Kate S.
- Our obsession with animals (Aldi coyote, Quiznos coyote, downtown foxes, etc.)
- Creative names for wildlife (e.g., Monty & Rose, Chance the Snapper, Chonkosaurus)
- Feral cats who get rid of city's rats
- “Pigeons!! They stick it out through the winter. True Chicagoans!” — Lauren M.B.
Proud Chicagoans
- “I love how tribal TRUE (born and raised) Chicagoans are. We love our city, flaws and all, and don’t take kindly to outsiders knocking our home.” — Brandon P.
- “My neighbors! I love that I live in a big city, but my neighborhood still feels like a neighborhood. I love how people are willing to get to know each other and help their neighbors out.” —Andrea
- All the people trying to make Chicago better
- Mama Gloria
- Timuel Black
- Jane Addams
- Trash People of McKinley Park
- "King of Chicago Weather," Mr. Tom Skilling
- "Great tour guides like Shermann Dilla Thomas and Mike McMains" — Sidney M.
- Mama Fresh
- “All of the hardworking, amazing gardeners and farmers across the city who are ready to throw down for our neighborhoods and grow way better food than what's at our disappearing grocery stores.” — Viviana O.
- “People are friendly.” — Sam B.
- “Meeting and chatting with other dog walkers in my neighborhood during my regular walks with my dog!” — Amelia H.
- “The kindness of total strangers — it's why we moved here!” — Morgan D.
- "That one guy that screamed in my face on the Blue Line my first day in Chicago" — Caroline P.
- "People who sell loud on the train." — Jacoby C.
- "My big Chicago family including my 27 nieces and nephews!" — Bob Z.
- "The old man with the flawless jumper at Marshfield park" — Jacoby C.
- “Tara at Esquire Barbershop.” —Alex T.
- "My hair girl Maria!" — Caroline P.
- “My pozole lady, Lupita!” — Giselle V.
- Watermelon Man on Stony Island and Baylor's Melon Market
- “Being in a bar when Claudio, the best damn tamale guy in our city, walks in with his red cooler” — Lawrence B.
- Mr. B at Old Fashioned Donuts
- The humor and bluntness of Poochie from the Wiener's Circle
- “Chicagoans got good jokes!” — Andrea
- Robin Williams
- Hannibal Burress
- Jane Lynch
- Bernie Mac
- John C. Reilly
- The Belushis
- Keke Palmer
- D-Wade
- Street performers
- State Street Preacher
- "Street singers like Andrew David" — Sidney M.
- "Street saxophonists, especially the person I always hear in Lincoln Square." — Simone A.
- Bucket Boys
- DJ Iggy and East Room Fatty at Easy Does It
- Buddy Guy
- Pivot Gang
- Do or Die
- Noname
- Jamila Woods
- Chaka Khan
- Earth Wind & Fire
- Mavis Staples
- Lucy Smith Collier
- Mahalia Jackson
- Lillian “Lil” Hardin Armstrong
- Lorraine Hansberry
- Andre Braugher
- Michael Clarke Duncan
- John Malkovich
- Nichelle Nichols
- Harrison Ford
- “Chicago's Jennifer Hudson is an EGOT winner!” — Sidney M.
- The poets
- Gwendolyn Brooks
- Margaret Burroughs
- “I love that Chicago can claim Shel Silverstein and all the stories he wrote (wish I got his stamp a few years ago).” — Sidney M.
- The authors
- Nate Marshall
- Eve Ewing
- Natalie Moore
- Jonathan Eig
- Sandra Cisneros
- Muralists
- Richard Hunt
- Korporate
- Jesse White Tumblers
- Local clothing designers
- “We can claim fashion icons like Law Roach and Virgil Abloh” — Sidney M.
- Our unions
- Hazel Johnson
- Fred Hampton and the Black Panther Party
- Jean Baptiste Point du Sable and Kitihawa
- Bessie Coleman
- How excited people are about prominent Chicagoans wherever you go domestically or internationally (e.g., Michael Jordan, Oprah, Joe Freshgoods.)
- “The City Cast Chicago team! (Jacoby, Simone, Michelle) And City Cast past (Carrie, Sidney).” — Alex T.
- Larry and Robin on WGN
- “Taylor Bell. He was a legendary H.S. sports journalist at the Sun-Times. He's a member of the Chicago Journalism Hall of Fame and recently received the IHSA's Distinguished Media Service Award.” — Bob Z.
- “Tom Lemming. One of the first, if not THE first, high school recruiting analysts. A Chicago native, he hosted The Lemming Report on the CBS Sports network and was featured in the book The Blind Side along with a cameo appearance in the Academy Award nominated movie.” — Bob Z.
- Siskel & Ebert
- “As a transplant from another northern Midwest city, I think the people of Chicago are TOPS.” — Jessica C.
- And finally … everyone who contributed to this list 🩵


