photo credit: Sandy Noto

The Ultimate Chicago Summer Festival Guide feature image


The Ultimate Chicago Summer Festival Guide

The best festivals where you can eat, drink, and party.

During the summer we have about 6,934 street festivals to choose from each weekend. And because nothing makes you feel like you took full advantage of Chicago's three months of decent weather like leaping over beer puddles while balancing a paper plate stacked with food in one hand, you'll want to use this guide. It's a running list of the festivals you need to prioritize for Summer 2022. These ones have the best food, vibe, and overall “feel-good factor.” 

Print this out, laminate it, and consult it every weekend.

All festivals are free or have suggested donations only unless otherwise noted. This is a running list so check back in for the latest details.

June 2022

The Ultimate Chicago Summer Festival Guide feature image

photo credit: Brant Cox

Do Division

Wicker Park, June 3-5

This isn’t a food festival, but the Wicker Park street fest has plenty of great vendors along with great bands, a fashion show, art, and kid’s activities. Check here for the full line-up of events.

Lincoln Park Greek Fest

Lincoln Park, June 3-5

Lincoln Park Greek Fest takes place on the grounds of St. George Greek Orthodox Church, and includes tons of food, music, dancing, and art. More info here.

Windy City Hot Dog Fest

Portage Park, June 4-5

As the name suggests, hot dogs are the focus of this brand new festival in Portage Park. Different hot dog spots will compete for who has the best dog, and you’ll get to judge. Plus there will be a mainstage for musical acts. Check here for the full lineup.

Fiestas Patronales Puertorriqueñas

Humboldt Park, June 9-12

If you’re in the mood for Puerto Rican food (trust us, you are) head to Humboldt Park for Fiestas Patronales Puertorriqueñas. Along with live music and art, there will be vendors selling things like pasteles, jibaritos, tostones, arroz gandules, and more. Check here for more info.


The Loop, June 11

You can find this traveling vegan food festival all over North America—in NYC, Toronto, LA, Miami just to name a few. Vegandale Chicago takes place in the Loop, and has local vendors like I Can’t Believe It’s Not Meat, Mi Pi Pizza, Homegirl’s Hummus, and more. You can also expect cruelty-free shops, and plenty of pleather. Check here for more info.

Andersonville Midsommarfest

Andersonville, June 10-12

After two years, Midsommarfest in Andersonville is back and, as far as we know, is 100% pagan-cult free. But what it lacks in Florence Pugh it makes up in local bands, Swedish art, and local food. More details here.

Taste Of Chicago Austin

Austin, June 11

We normally avoid the Taste of Chicago in Grant Park. It's expensive, crowded, and has boring food. But this year we're intrigued—they're doing spinoffs in different neighborhoods across the city, highlighting food from that community. The first one is in Austin, and you can click here for the vendor lineup.

Taste Of Randolph Street

West Loop, June 17-19

Randolph Street, ever heard of it? Yes “Restaurant Row” has its own little “Taste of” and naturally it’s stacked with great food from neighborhood restaurants. Check here for the full lineup.

Chicago Pride Fest

Lakeview, June 18-19

This LGBTQ festival in Lakeview is full of drinks, drag queens, dancing, rainbows, and plenty of food. This year’s Pride will have over 100 vendors and three stages for live music. Details here.

Taste Of Chicago Pullman

Pullman, June 18

This is the second festival spinoff from the Taste Of Chicago series, highlighting food from Pullman. Along with food, they'll have live music and dance performances, and you can click here for the lineup.

Taste Of Chicago Little Village

Little Village, June 25

The third and final spinoff from the Taste Of Chicago series takes place in Little Village. Look for lots of incredible Mexican food, including vegan specialties from Healthy Substance and plenty of paletas. Check here for the full lineup.

July 2022

The Ultimate Chicago Summer Festival Guide feature image

West Fest

West Town, July 8-10

West Fest has been around since 2004, and after going virtual in 2020, is back in full force. Located in West Town, you can see music acts organized by The Empty Bottle, and food trucks from neighborhood restaurants. They also have Pet Fest: a cute area dedicated to dogs and dog-friendly activities. More details here.

Taste Of Chicago

Grant Park, July 8-10

We normally avoid the Taste of Chicago in Grant Park. It's expensive, crowded, and has boring food. But this year we're intrigued—in June they did spinoffs in different neighborhoods across the city, highlighting food from that community. This has renewed our hope. So if you find yourself with a hankering to visit Buckingham Fountain this weekend, here's the lineup.

Roscoe Village Burger Fest

Roscoe Village, July 15-17

Another straightforward food festival. The Roscoe Village Burger Fest has around 10-15 burger vendors to choose from, including Fatso’s Last Stand, Tandoori Char House, and Byron’s, which we know is a hot dog spot, but also has tasty burgers. Stay tuned for the full lineup here.

Tacos Y Tamales Fest

Pilsen, July 15th-17th

This Mexican festival takes place in Pilsen on the stretch of 16th street with all the colorful murals. And the food here isn’t just from restaurants—you’ll find coolers and carts helmed by locals. There are tacos and tamales filled with chicken and green mole, steak and red mole, pork ground beef, kale, cheese, and just about anything else. There are also other dishes like enchiladas, tortas, elotes, churros, and piña coladas along with art and music. Check here for info.

Silver Room Sound System Block Party

Oakwood Beach, July 16-17

After a two-year hiatus, this Hyde Park music festival is finally back and has been moved to the beach. This means a ton of different musical performers and of course, food. Check here for the lineup and ticket prices.

Taste of Lincoln Avenue

Lincoln Square, July 22-24

The Taste Of Lincoln Avenue festival has been around for 40 years and is a consistently well-organized, fun time. Along with lots of neighborhood restaurants, there are arts and crafts, and one main music stage—which we’ve learned to appreciate after hearing battle-of-the-bands competing from different stages for our attention. More info here.

Bantu Fest

Hyde Park, July 23-24

There are over 30 African countries represented in this year’s Bantu Fest, a multicultural family-friendly festival in Hyde Park. This means a ton of different music, performances, art, and of course, food. Check here for details.

Fiesta Del Sol

Pilsen, July 28-31

Fiesta Del Sol is a free four-day family-friendly Mexican festival in Pilsen. This event spans an eight-block space down Cermak Road, has carnival rides, and over 100 booths with tacos, tamales, and tostadas. More info here.

Lincoln Square Greekfest

Lincoln Square, July 29-30

This festival is hosted by St. Demetrios Greek Orthodox church, and will have Greek food (with pastries and treats like loukoumades) live performances Friday, a Greek dance troupe, and a Hellenic marketplace. Check here for details.

Chinatown Summer Fair

Chinatown, July 30-31

Chinatown Summer Fair, how we love you, let us count the ways. This iconic event has tons of food, art, and music. This year’s Chinatown Summer Fair will open with a lion dance procession, followed by performances, including kung fu demonstrations, a breakdance competition, K-pop entertainment, and a dumpling eating contest. Check here for more information.


Grant Park, July 28-31

You know the deal, it’s Lollapalooza. Lineup and tickets here

August 2022

The Ultimate Chicago Summer Festival Guide feature image

Windy City Smokeout

United Center, August 4-7

Windy City Smokeout is pricey (single-day tickets start at $45), but it’s always a lot of fun. There’s great BBQ from all over the United States, and musical performances from country singers like Tim McGraw—who we only just remembered because of Yellowstone. Tickets and the full lineup, here.

Northalsted Market Days

Northalsted, August 5-7

Northalsted Market Days is a weekend-long live music street festival celebrating the LGBTQ community in Northalsted (a.k.a. the neighborhood formerly known as Boystown). The festival is huge, with six stages dedicated to live music, over 250 vendors, art, food, booze, plus DJs and dancing. Check here for more info.

Ribfest Chicago

North Center, August 19-21

The moment has arrived: Ribfest. This is one of the best festivals in the city, with tents full of smoky meat as far as the eye can see. Check here for the full lineup.

Chicago Caribbean Carnivale

Hyde Park, August 20

It’s a one-day-only Carnivale in Hyde Park. Expect dancing, music, and Caribbean food like roti, festival, jerk, and more. More info here.

Pilsen Fest

Pilsen, August 20-21

Pilsen Fest is a Mexican festival with bands, art, and food stands like tacos with handmade tortillas. Check here for info and updates.

Taste Of Greektown

West Loop, August 26-28

This festival has been in the West Loop for over 30 years, taking place on the strip of Halsted that’s been the center of Chicago’s Greek restaurant scene for decades. There will also be plenty of music and entertainment (including Greek bands) games for kids, and food from restaurants like Artopolis and Athena. More info and updates here.

September 2022

The Ultimate Chicago Summer Festival Guide feature image

photo credit: Christina Slaton

Taste of Polonia

Jefferson Park, Sept 2-5

This is the 40th Anniversary of the Taste of Polonia Festival. This Polish festival in Jefferson Park has live music, dance performances, Polish food and beer, exhibitions, a casino, beer garden, and a kid's area with activities like face painting. Local restaurants include Tata’s Pierogis, Alex bakery, and Babushka Polish Foods. Check here for more info.

German American Oktoberfest

Lincoln Square, Sept 9-11

Yep, we’re heading into Oktoberfest territory, which means the end of summer is almost here. Celebrate at this festival in Lincoln Square, which has German food, drinks, beer, and German bands. More info here.

Lakeview Taco Fest

Lakeview, Sep 17-18

This is the ninth year of Lakeview’s Taco Fest. Eight restaurants are participating in the annual taco contest, including Juanita’s Mexican Food, Taqueria La Ciudad, Tacos Nietos, and El Campeón. There will also be drinks and music. Check here for more details.

Suggested Reading

The Best New Patios In Chicago guide image
The Best New Patios In Chicago

The best new places to eat and drink outside this summer.

The Best Patios In Chicago guide image

Our guide to Chicago’s all-time best summertime spots.

Where To Go To Pretend It’s Not Winter guide image

The guide for when you’d really just rather be on vacation.

Infatuation Logo
2023 © The Infatuation Inc. All Rights Reserved.


Get it on Google PlayDownload on the App Store