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City Cast Chicago

Sidney Madden

While the Chicago flag is seen everywhere from buildings to tattoos, <a href="https://commons.wikimedia.org/wiki/File:Flag_of_Illinois.svg">Illinois’ state flag</a> is less well-known. That’s probably because it’s just not very good, says “<a href="https://nava.org/good-flag-bad-flag">Good Flag, Bad Flag</a>” author Ted Kaye. <a href="https://www.ilga.gov/legislation/BillStatus.asp?DocNum=1818&amp;GAID=17&amp;DocTypeID=SB&amp;LegId=146496&amp;SessionID=112&amp;GA=103">State lawmakers are exploring a flag redesign</a> in hopes more people will fly it. While those recommendations wouldn’t come until next year, Kaye tells host Jacoby Cochran why we should care what our flag looks like and what makes a good one. Want some more City Cast Chicago news? Then make sure to sign up for our <a href="https://chicago.citycast.fm/newsletter/">Hey Chicago newsletter</a>.  Follow us <a href="https://twitter.com/CityCastChicago">@citycastchicago</a> You can also text us or leave a voicemail at: 773 780-0246 Interested in advertising with City Cast? Find more info <a href="https://citycast.fm/advertise/">HERE</a>

Why Chicago's Flag Rules, and Illinois' Flag Doesn't

Statewide voting starts soon with 10 finalists, the current flag, and two vintage flags in the running. Read more about the 

Hey Chicago wants to know: Which one is your favorite?

Illinois' current state flag could be seeing its final days with a new statewide poll soon to be underway. (

Emily Mack

Fests, fireworks, food, and freshwater fun — there’s a lot to do in Chicago in July. Here’s a guide to keep it all straight.

Fourth of July is always lit in the city — from lakeside shenanigans to big fireworks shows to, er, less official neighborhood displays. In honor of America’s 250th, Navy Pier is showing its 

. Meanwhile, our City Cast Chicago team talked with those 

Fitzgerald’s 43rd American Music Festival

African/Caribbean International Festival of Life

July is full of fests well beyond the Fourth, too:

 | Blue Island Avenue between Cermak and Wolcott | Pilsen 

 | Wells Street between Ontario and Chicago

 | Cermak between Ashland and Morgan | Pilsen | Free

 | Lincoln Avenue between Altgeld and Fullerton | Lincoln Park

 hot enough to enjoy time out on (or in) the water — that’s no longer the case. Of course, Chicago has no shortage of splashy activities:

I just took a lovely ride on the lake with 

 — shout out to wife-co-captains Gina and Steph ❤️

 as a descendant of Friday Morning Swim Club!

And if you’re not a planner, there are always 

As I write this, I am sitting directly in front of my window unit. And I suggest you do the same. As high temps continue, storms ahead this weekend may help Chicago cool down, but those 

there were gaps in the city’s cooling network

There’s a lot to do in Chicago in July. Here’s a guide to keep it all straight.

Your Guide to July 2026 in Chicago

Everything to know about Chicago neighborhoods: Where to go, eat, shop, drink, and more.

Chicago Neighborhood Guides

Neighborhood Guides

 in Woodlawn. And while you’re there, take a walk around the neighborhood to see some of our favorite sights. Including, but not limited to, a certain hometown president’s new library.

, we want to highlight other spots to visit while you’re in the area.

If you managed to snag tickets, begin your walk at the Obama Presidential Center. If not, don’t worry — 

Build is the perfect way to start a morning in Woodlawn. In addition to coffee on us, they’ve got a banging breakfast sandwich and 

 about social justice and local politics.

, a community center that’s also home to 

Experimental Station also hosts the 61st Street Farmers Market every Saturday: “

The best place to experience diversity in a segregated city

,” as our friends at South Side Weekly say.

Continue down Blackstone Avenue, and you’ll hit 

. The perfect spot to sit and read a zine you picked up at Build!

From there, head down Dorchester Avenue till you hit the 

. Here, non-OPC-ticket-holders can enjoy a mosaic of Barack and Michelle.

out of the way. But it's absolutely worth a stop for lunch. They’ve got homemade ice cream sandwiches, smoothies, mini cheesecakes, paninis … When you’ve hit the shipping container on Woodlawn Avenue, you’ve made it.

From there, it’s a 15-minute walk east to Stony Island Arts Bank.

 is not in Woodlawn — it’s just over the border in Greater Grand Crossing. But we’ll take any excuse to plug this one-of-a-kind space.

Artist Theaster Gates turned the century-old abandoned bank into an exhibition space and archive in 2015. Now, after recent renovations, it’s reopened with 

a conceptual tea salon and cocktail lounge

More great spots near OPC

A Guide to Woodlawn — Plus Coffee! 

Have you been following the news in Chicago this week? Prove it! Take the City Cast Chicago news quiz.

Looking for a previous Hey Chicago news quiz? Find it here.

How closely were you paying attention to this week's current events? Test yourself in our weekly trivia quiz.

Your Weekly News Trivia Quiz

Take This Week's Chicago News Trivia Quiz

What Chicagoans have been wondering. We break down why things in Chicago are the way they are and how they work.

Chicago, Explained

Chicago’s mayoral election is Feb. 23, 2027 — if no candidate gets a majority of the vote, a runoff will take place April 6.

far-off, but the race has already begun! Candidates are announcing, and money is pouring in — here’s where the race stands so far. 

 has been the state’s chief fiscal manager since 2016. Though she ran unsuccessfully for mayor in 2019, this campaign feels more focused. She’s not seeking another term as comptroller and she's using social media to amplify (

A centrist Democrat, Mendoza is pro-police and has said that Chicago is facing 

 while serving his ninth term in Congress. Unlike Mendoza, Quigley is up for reelection in the general this fall.

 seems focused on addressing the city’s $1 billion-plus deficit.

Cook County Board of Review Commissioner George Cardenas 

officially launched his campaign last week. And so far, his platform seems relatively moderate — 

. Previously, Cardenas spent nearly 20 years as 12th Ward alder, serving as an ally to former Mayors Lori Lightfoot, Rahm Emanuel, and Richard M. Daley.

Chicago Housing Authority board member Matthew Brewer

 slammed Johnson while announcing his candidacy. The two have a contentious history 

 for his November reelection race … but Giannoulias doesn’t need big contributions to trounce a little-known Republican challenger. Seemingly, Giannoulias is shaping up to run for mayor.

Giannoulias is generally considered to have improved office (and line) conditions … but in 2010, 

the collapse of his family's bank cost him the U.S. Senate election

. Giannoulias lost to Republican Mark Kirk.

 is seeking reelection for her current role in November, though she’s previously said 

Pappas has served as treasurer since 1998 and recently published a damning report detailing 

 … but she’s perhaps best known for her 

has not formally announced his reelection campaign, though it seems likely. Then again, Johnson’s 

. Unlike past mayors, Johnson does not maintain a rubber-stamp majority in City Council.

 run again — but for now, he’s still dealing with 

debt and ethics fines from his previous campaign

So, Who’s Running For Mayor?

Kayleigh Padar

Seeing Chicago’s vibrant queer community come out in full force as the whole city launches into summertime always reminds me why I love living here.

I’m especially looking forward to the Pride Parade on Sunday. This year is particularly special because it falls on my birthday! I can’t think of a better way to celebrate than putting some glitter on my face and soaking up thousands of people’s sheer joy.

I’ve rounded up some of my favorite LGBTQ+ owned businesses that keep Chicago bright and colorful all year long. For even more recommendations, check out City Cast Chicago contributor Anna DeShawn’s 

Iced coffee, bagels, and tarot, oh my! This community-centered coffee shop has quickly become a staple in the neighborhood. I swear, every time I walk by, there’s a line out the door. It offers a wide range of pastries, including vegan and gluten-free options, and they create a new zodiac-themed drink every month. The cafe hosts a slew of community events, from crafting meetups to comedy shows to tarot readings.

Open since 1980, it’s one of the city’s oldest LGBTQ+ bookstores and a place that’s easy to get lost in. Its multiple rooms of winding shelves are home to an unparalleled collection of LGBTQ+ literature, plenty of fiction and poetry, and an extensive section on sale. This 

 shows how the bookstore has evolved in the last 45 years.

This vintage shop has been “making Bridgeport weirder since 2022,” with its wide selection of clothing, art, and everything in between. The owners remake, remix, and repair antiques to give new life to timeless treasures. New items drop in-store every week, and you can also buy 

On a quest to increase the dwindling number of lesbian bars throughout the country, one queer couple opened a neighborhood cocktail lounge “for every friend of Dorothy.” The subterranean, 70s-inspired speakeasy is known for its arts-focused events, including silent reading nights, open mics, movie nights, and more. It’s a little tricky to find the first time, but don’t let that deter you. Look for the unmarked red door on Chicago Avenue just west of the “2500” painted on the building.

LGBTQ+ Owned Businesses in Chicago

Keep It Local

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Keep It Local with City Cast Chicago

 became the local chain of thrift stores we know today, it took shape as a series of garage sales created in response to the HIV/AIDS crisis.

Howard Brown Health founded the organization because so many people were dying and leaving behind entire homes full of belongings. Many families refused to take their things due to the stigma surrounding the disease, so the LGBTQ+ clinic stepped in.

Brown Elephant moved into its first storefront in 1982, and is now located in Northalsted at 812 W. Belmont Ave. and Andersonville at 5404 N. Clark St.

“Our name comes from the Brown in Howard Brown Health, and at the time, AIDS was known as the elephant in the room, so that’s why we’re Brown Elephant,” said Northalsted store manager Matt Talaga-Roman.

Ever since then, Brown Elephant has sold donated furniture, clothing, and household decor to raise money for Howard Brown Health, which serves more than 40,000 people each year.

“There have been times throughout Howard Brown Health’s history when funding from the Brown Elephant was the reason the organization survived,” Talaga-Roman said.

In the past fiscal year, Brown Elephant has provided more than $100,000 in vouchers for clinic patients and young people experiencing homelessness who visit Broadway Youth Center. The vouchers are exchanged for items at the store.

“It’s our way of giving back directly to our local community,” Talaga-Roman said.

Plus, as a shopper, there’s a lot to love. Brown Elephant accepts and sorts more than one million pounds of donations, making it the perfect place to find an emergency dress or a housewarming gift.

New items are added to the stores every day. Both locations run a “Monday Mayhem” sale every week, when all clothing is 50% off.

All this to say, you can feel good when you pick up that new-to-you crystal dish you don’t really need.

Before Brown Elephant became the local chain of thrift stores we know today, it took shape as a series of garage sales created in response to the HIV/AIDS crisis.

Brown Elephant’s Legacy of Giving Back

Juneteenth weekend was extra bustling in Chicago this year, thanks to the Obama Presidential Center opening. The big party was Thursday night, followed by three more days of activities and performances.

It’s no surprise the city went so hard for Barack Obama — love him or hate him, he’s a Chicago legend. The same goes double for Michelle.

See how well you know their Chicago roots.

Test Your Knowledge of the Obamas in Chicago 

Back in April, I said every month feels like poetry month in Chicago. I feel the same way about Pride — this city stays bursting with queer energy. But, in honor of 

 Pride month, here are some local LGBTQ+ poets worth checking out.

 and all-around hometown hero. She’s also a decorated poet, often mining her Beverly upbringing for her work.

 you don’t fit in / everybody in your neighborhood color of white hen

Woods’ friendship with another local queer poet, Fatimah Asghar, inspired the series “Brown Girls.” 

Rachel Mennies is a Chicago-based writer whose poems get at queer longing. Her collection 

 is full of epistolary poems, written to the woman the speaker loves.

 / through my coat, enough to pool desire / where I most wanted you to touch me.

Britteney Black Rose Kapri is — I can attest — a great (though tough) poetry teacher. She’s published two books of poetry, including 

, as in dwelling, as in crib, as in where your inhibitions go to rest.

Born in Colorado, Katana Smith is now based in Chicago and previously served as Northwestern University’s artist-in-residence. Her poems 

 are an excellent package: petty and moving.

Maybe I was the only friend who would talk to you about him … I would have talked to you about literally anything.

Oli Rodriguez is an artist and writer born in Chicago whose intersectional work explores the AIDS pandemic.

 tells the story of a “sondaughter” raised in gay bars — and recalls the cruising hotspot that was Belmont Harbor.


📖 Read more Chicago poetry!

These local queer poets are worth checking out — during Pride month and beyond.

5 Queer Chicago Poets You Should Know

Find the best of everything that Chicago has to offer.

Chicago’s Best

Chicago's Best

Pick from 10 finalists, the current flag, and two vintage flags in our poll. 

Vote on Illinois' New State Flag!

What Should Illinois' New Flag Be?

What's being decided in Chicago City Hall and why it matters. We monitor local elections, political news, and Chicago City Council. 

Chicago Election and City Hall News

Local Civics

. But during Chicago’s 2022 midterm primary, just 22% of the city voted. We can do better than that!

It’s Election Day Today … and Tomorrow? Plus, Our Summer Plans at Ravinia

 and the city’s downtown supersite will continue operating through 7 p.m. today. Same-day registration is available at all those sites, plus additional 

Here’s what you’ll need for same-day registration.

Already registered? Today, you can hit your local polling site — 

, make sure your ballot is postmarked today! Vote-by-mail procrastinators should consider dropping ballots off at an early-voting spot.

The retirement of longtime Sen. Dick Durbin has opened up a competitive Democratic race, currently dominated by three front-runners: 

Other competitive congressional races are happening in the 2nd, 7th, 8th, and 9th Districts:

 are running to replace Krishnamoorthi, including 

 Thirteen candidates want to succeed retiring U.S. Rep. Danny Davis, including 

Fifteen candidates hope to succeed retiring U.S. Rep. Jan Schakowsky. Among them: 

Cook County Board President Toni Preckwinkle faces 

 from (the relatively conservative) Ald. Brendan Reilly (42nd).

 are vying to become comptroller, aka the person who pays the bills in Illinois.

As property taxes rise, the Democratic party has 

 Cook County Assessor Fritz Kaegi, supporting suburban challenger Pat Hynes.

The Cook County Board of Review also faces a potential shakeup, following 

Actually, I can’t tell you who to vote for … but I can help you get informed! Consider consulting these heavily researched guides:

 both allow for easy comparison between candidates.

 offers helpful details for evaluating judicial candidates. (This year, though, 

 is a progressive independent option with a casual tone

 aims to appeal to young voters and includes many visuals

More on the biggest races we’re watching 👀

In Chicago, primaries often decide winners. So go vote!

Your Last-Minute Illinois Primary Election Guide

Your Last-Minute Election Guide

Don’t forget — the Illinois primary is coming up in March. And as any Chicagoan can tell you, that’s where the action is.

Here are the big races we’re keeping an eye on

Across both parties, 17 (!) candidates are running to replace longtime U.S. Sen.

Dick Durbin, who is retiring after nearly 29 years in the Senate. 

 are perhaps the most well-known names in the crowded race.

Krishnamoorthi was first elected to the 8th district in 2016. 

He’s also the biggest fundraiser in the race

 in 2013 to replace Rep. Jesse Jackson Jr. after his sudden resignation amid an investigation into campaign finance fraud. Stratton became Gov. JB Pritzker’s running mate in 2018 and has served as his lieutenant ever since.

Those three Democrats recently released their economic proposals

On the GOP side, the former state party chair Don Tracy is (somewhat) well-known. He resigned abruptly in 2024, just before the RNC, 

. Tracy is more of a pre-MAGA Republican.

Kelly and Krishnamoorthi are stepping down from their current positions as they vie for the Senate.

The Illinois primary is coming up in March — and that’s where the action is. Here are the races we’re keeping an eye on.

Local Civics

What Should Illinois' New Flag Be?

Sidney Madden

City Cast

Why Chicago's Flag Rules, and Illinois' Flag Doesn't

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Local Civics

Your Last-Minute Election Guide

The Primary Races to Watch

Donald Trump and the Terrible, Horrible, No Good, Very Bad Week in Court

Why You Can Thank Chicago for Labor Day

How Alders Maintain Control of Their Ward

City Council Nepo Babies: The Quiz

What Reduced Parking Mandates Mean For Chicago

Weigh in on Your Ward’s Budget

The latest in Chicago

Your Guide to July 2026 in Chicago

A Guide to Woodlawn — Plus Coffee!

Take This Week's Chicago News Trivia Quiz

So, Who’s Running For Mayor?

LGBTQ+ Owned Businesses in Chicago

Brown Elephant’s Legacy of Giving Back

Test Your Knowledge of the Obamas in Chicago

5 Queer Chicago Poets You Should Know