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City Cast Chicago

The end of summer can feel tragic in Chicago, but don’t worry — 

temperatures shouldn’t drop consistently till the end of the month

. That means there are about 30 warm days left. Take advantage!

Stave off the end-of-summer blues with jazz. You can kick things off Sept. 1 at the 

 for $25. Later in the month, free options include:

 | Willie Dixon’s Blues Heaven Foundation | South Loop

Meanwhile, other fests continue all over the city. Art lovers, consider 

And for the foodies: two Oktoberfests — one in 

, Riot Fest is back in Douglass Park this year Sept. 19-21. To strike a deal, Riot Fest pledged an additional $1 million to the park over the next five years.

This year’s headliners include Blink 182, Weezer, and Green Day. And — probably — John Stamos will perform. Fest founder “Riot Mike” just got a 

 on his leg, which was one of the actor’s demands to drum for the Beach Boys’ set. 

Riot Fest has a longstanding meme-y obsession with the actor.

 at Soldier Field against the Minnesota Vikings. Will you be tailgating? This year could be one of the last to darty outside the ol’ Spaceship stadium. As of now, building a new Bears stadium in Arlington Heights is 

54th Annual Mexican Independence Day Parade

 will take place Sept. 14 along 26th Street, while the accompanying fest, 

This year’s theme is “Pride and Power: Our Strength, Our Legacy.”

The last couple Emmy Awards were a source of hometown pride as “The Bear” swept. This year, TV’s biggest night takes place Sept. 14, and “The Bear” is nominated in 

 … but I still love seeing Chicago repped at awards shows.

 is a twice-yearly phenomenon when the sun lines up perfectly with Chicago’s grid. This fall, it’ll happen

Sept. 22-25. Head to the Loop to capture building-framed shots, but you should be able to see the burning orange golden hour from just about any east-west street.

Got other things you’re excited for in September? Hit us up at 

The end of the summer can feel tragic in Chicago. That's why we're not calling it the end of summer.

Your Guide to Chicago in September 2025

Find the best of everything that Chicago has to offer.

Chicago’s Best

Chicago's Best

, we're testing the knowledge of some of our City Cast Chicago members on the podcast. Play along with the quiz below!

The quiz is broken up into five different categories: Getting Around, Chicago Poetry, Chicago Jingles, Chicago Politics, and The Great Chicago Fire. The first question of each category is on the easier side and is worth one point. The second question of each category is more difficult and is worth five points.

On today’s podcast, we test the knowledge of some of our City Cast Chicago members to see how well they know Chicago. Play along with us!

The Ultimate Chicago Quiz

How Well Do YOU Know Chicago?

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

Chicago, Explained

Between Valentine’s Day and other holidays, there’s lots to love about Chicago in February. Here’s how we’re making the most of the month.

Making dinner reservations around Feb. 14 can be competitive. Plan a unique date instead to a board game cafe like 

 are fun and all, but take inspiration from these locals who 

Lunar New Year celebrations are underway between 

. But we’re perhaps most excited about parades on 

The monthlong commemoration has roots on the South Side. Now, Chicagoans can seek out the new 

If you love the 1993 Bill Murray movie filmed in Woodstock, Illinois, head to the northwestern town for 

 this weekend. Events include a musical adaptation of the film, walking tours, groundhog trivia, and a themed 5K. 

 is also hosting its second annual celebration Sunday.

A production of “A Raisin in the Sun?” A play about the 

 that inspired the lottery? Choose from more than 100 performances for as low as $15 during the 

Watch the Super Bowl with other bitter Bears fans at the 

 at Soldier Field on Feb. 9. Rooting for the Birds? Head to 

 in Roscoe Village. Part of Chiefs Kingdom? Watch the game from 

 in Wrigleyville. Now is the time to get your ticket for 

Kendrick Lamar and SZA’s Chicago concert

 before prices increase after the halftime show.

Craving spring? So is everyone else in Chicago. Book your reservations ASAP for the 

Lincoln Park conservatories’ flower shows

 opening Feb. 12. The team shared tips last spring for how 

Between Valentine’s Day, Lunar New Year, and Black History Month, there’s lots to love about Chicago in February.

Your Guide to Chicago in February 2025

Don’t let August slip away into a moment in time — enjoy the last of summer and prep for the new school year.

Hundreds of thousands of festivalgoers will be at Grant Park to see big acts like SZA, Chappell Roan, and the Killers this weekend. If you’re going, take care of yourself and others. That could mean 

learning to administer an overdose reversal drug

Prepare yourself for traffic and protests: The 

 is taking over the United Center, McCormick Place, and surrounding areas leading up to and during the event Aug. 19–22.

That’s also when your favorite restaurants near the venues are 

 — consider supporting them more this month.

Lisa Beasley’s “Unpolitical Women” show

Cue the sad music: Some Summertime Chi programming is coming to an end 🎻 

 in Millennium Park are wrapping up this month. The 

Museum of Contemporary Art’s Tuesdays on the Terrace

Amid teacher contract negotiations and a controversial budget

What can families do to prepare? Get school supplies — check out 

 for your vegan student. Ride the CTA on the first day of school — it’s free!

We didn’t forget about educators: The Creative Chicago Reuse Exchange in Auburn Gresham has a 

? The DNC? Just before the school year starts? Stay tuned for an upcoming City Cast Chicago episode with with 

 who recommends spots to eat in places like Milwaukee and Cleveland.

Your Guide to August in Chicago

Chicago’s summer festival season is here! But with multiple events every weekend, planning your lineup can be overwhelming.

That’s why we’ve got this curated list of the fests we can’t miss, the best fest bites, and some music fest lineups we’re watching.

The City Cast Chicago podcast team picked their No. 1 must-visit fest of the season and laid out the rest of their summer itinerary.

 June 14-16 at SeatGeek Stadium in Bridgeview

: The performers. Mick Jenkins is performing a 10th anniversary set for his mixtape “The Waters,” and Chief Keef is performing in the Chicagoland area for the first time in over a decade.

African/Caribbean International Festival of Life

 July 4-7 in Hyde Park. For something new, 

: The joy. Plus, the lineup offers big names throughout the day from JoJo Siwa and Bob the Drag Queen in the afternoon to Natasha Bedingfield and Amber Riley in the late evening.

 July 12-14 in Jefferson Park. For a fest with a twist, 

 Sep. 6-8 in Norwood Park. For the food, 

: The history. The first fest celebrated the community’s successful efforts to pressure the Chicago Board of Education into building what is now Benito Juarez High School.

: Pack your fests into one weekend. In addition to Fiesta del Sol, 

If you wanted, you could plan your entire summer just around Chicago’s food festivals. Here are some of the food-focused fests that we’re saving room for.

Make sure you leave room for the weekend of July 19-21 when you can catch both 

 will once again run pop-ups in Rogers Park in June, Marquette Park in July, and Pullman Park in August before the September fest in Grant Park. You can also catch the 

Ravenswood will hold two different beer-focused fests: Catch the 

 July 20-21. Lincoln Park will also hold 

In addition to the plethora of neighborhood festivals in the city, Chicago is home to two of the biggest music festivals in the country: 

Here are some other fests we talked about during festival week on City Cast Chicago.

With multiple events every weekend, planning your summer lineup can be overwhelming. That’s why we’ve got this curated list.

The Ultimate Summertime Chi Festival Guide

Tips and tricks for living your best Chicago life, by locals, for locals.

Chicago Life Hacks

You have one more week to donate to Love & Nappyness, the hair care drive dreamt up by Chicago rapper Matt Muse five years ago after he put out a 

. He sat down with Hey Chicago to share more about the fundraiser and how to get involved.

This interview has been edited for length and clarity.

What sort of products are you looking for?

“We're collecting paraben-free all-natural hair care, skin care, and personal hygiene products. … We'll take whatever, but [prefer] something that is useful more on the day-to-day. Hair dye, for example, is a great thing that we've gotten before, but is something that a person uses for fun. … Products that are more about the bare necessities (razors, toothbrushes, etc.) of self-care are what we're really looking for.”

“The benefit concert in tandem with the donation drive has been the biggest evolution.

“This year, we’ve been planning the show all year. The headliner is Ravyn Lenae. Joseph Chilliams has been releasing a lot of new music this year. 

, so this will be my first time performing.”

Have you heard from people who have benefitted from the fundraiser?

“I'm not big on fishing for people's opinion on what we do or getting those stories because I don't want to dehumanize the people who we’re helping. … It’s about, ‘Hey, if this will work for you, we hope it does. Thank you and you do what you got to do with it.’”

You have one more week to donate to Love & Nappyness, the hair care drive dreamt up by Chicago rapper Matt Muse five years ago.

Why This Chicago Rapper Is Collecting Hair Care Products

What Chicago celebrities, public figures and key citizens have to say about living here.

3 Questions With Chicago Public Figures

3 Questions With

 is where Old World meets modern Chicago. Farmers from Switzerland, England, and Germany settled in the area in the mid-19th century, bringing their culture to the area. Longtime resident 

Gretchen Eng joined us on the City Cast Chicago podcast

 to show us around the neighborhood and shared some of her favorite recs.

 is authentic. The first pandemic Thanksgiving when all of my friends were not going to visit family, everyone ordered takeout from 

. I think the best pizza place in the entire city is 

. It is New York style, but it's really good, especially if you like to fold your pizza.”

 is really important in the history of Chicago music, and there are all kinds of concerts that you can check out there. Because so many musicians live in the neighborhood, there are lots of pop-up jams.”

“Shopping is a big thing that brings people to Lincoln Square, especially when you have nothing you're looking for in particular. 

 has any toy you could possibly want to play with.”

 is a place where you can go to learn German, to learn how to cook German foods, and to experience German art exhibits."

Headed north for some folk and alt-country music at the 

? This festival features a lineup of live music, delicious food from local restaurants and vendors, and some of the best craft beer in town. The fest runs Friday through Sunday.

Want more Lincoln Square? We’ve got the 

guide to get you into the Bavarian spirit.

All About Lincoln Square

Longtime resident Gretchen Eng show City Cast Chicago podcast around the Lincoln Square neighborhood and shared some of her favorite recommendations.

Get to Know Lincoln Square in Chicago

Get to Know Lincoln Square

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

Chicago Neighborhood Guides

Neighborhood Guides

From Beyonce to Metallica to Blink-182, big artists are flocking to Chicago’s biggest venues. But don’t forget to support artists at smaller spots, too. We tapped City Cast’s growth manager Caroline Patton, who pens 

“What other venue can get you a slice of pizza, a beer–shot combo, and a show for $20ish? Plus, there are free concerts on Mondays!”


🕺 “The Promontory has great DJs and dance parties. Be sure to reserve a table ahead of time. Carol’s has the best honky-tonk space, weekly karaoke, and Nashville’s up-and-coming artists.”


👂 “This venue was designed for the opera, so the acoustics don’t compare to any other in the city.”


🚽  “Many of their bathrooms are gender-neutral. Pro-tip: Head downstairs during the show to the Punch House where there is never a bathroom line, and come up to enjoy the show with a fresh drink.”


🍻 “Bottom Lounge is huge, and right off the Green Line and Ashland bus. Sleeping Village opens its dog-friendly patio in the summer, and has occasional food trucks and one of the city’s most eclectic beer lists.”



Want to add to our list? Tell us your fav venue in the city and why.

The Best Concert Venues

From Beyonce to Metallica to Blink-182, big artists are flocking to Chicago’s biggest venues this year. But don’t forget to support artists at smaller spots, too. City Cast’s growth director Caroline Patton, who pens 

 in Ukrainian Village. 

“What other venue can get you a slice of pizza, a beer–shot combo, and a show for $20ish? Plus, there are free concerts on Mondays!”


 in Uptown

“The Promontory has great DJs and dance parties. Be sure to reserve a table ahead of time. Carol’s has the best honky-tonk space, weekly karaoke, and Nashville’s up-and-coming artists.”


 in the Loop

“This venue was designed for the opera, so the acoustics don’t compare to any other in the city.”


 in Pilsen

"Many of their bathrooms are gender-neutral. Pro-tip: Head downstairs during the show to the Punch House where there is never a bathroom line, and come up to enjoy the show with a fresh drink.”


 in Avondale

“Bottom Lounge is huge, and right off the Green Line and Ashland bus. Sleeping Village opens its dog-friendly patio in the summer, and has occasional food trucks and one of the city’s most eclectic beer lists.”

Starting tomorrow, Karaoke Storytellers will be hosting weekly 

 at Brando’s through March. You can spice up your mid-week with your fav singing-storytelling event co-created by City Cast Chicago’s Jacoby Cochran. Want a different karaoke experience? There’s a Chi bar for you 



WBEZ’s Susie An: “They have a system which pretty much opens the possibility of any song you could want to sing. It's like a YouTube search.”



Karaoke regular Davo Sounds: “It’s fun and easy to interact with the bar and room when the song is just right. Lots of regulars mixed with larger groups there for the night.”



Karaoke Storytellers creator Connor Gorman: “It’s open until 2 a.m., seven days a week — it’s always rocking.”


music

Your Guide to Chicago in September 2025

How Well Do YOU Know Chicago?

Your Guide to Chicago in February 2025

Latest articles

Your Guide to Chicago in September 2025

How Well Do YOU Know Chicago?

Your Guide to Chicago in February 2025

Your Guide to August in Chicago

The Ultimate Summertime Chi Festival Guide

Why This Chicago Rapper Is Collecting Hair Care Products

Get to Know Lincoln Square

Latest articles

Your Guide to August in Chicago

The Ultimate Summertime Chi Festival Guide

Why This Chicago Rapper Is Collecting Hair Care Products

Get to Know Lincoln Square

The Best Concert Venues

The Best Concert Venues

The Best Karaoke Bars