31 of the Best Things to Do in Chicago and the Suburbs in August 2022

Break up your everyday routine with a dose of summer merriment this August. With a number of inaugural events and others that support local organizations, it’s never too late to start new traditions that benefit you and the community. Whether it takes you to the suburbs or the heart of the city, you are sure to find summertime delight on our comprehensive list of what to do in the Chicagoland area this August!

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All Month

Art on the Mart

“explore” by Jonas Denzel | Photo courtesy of Carol Fox and Associates

This series has given a new life to one of Chicago’s most historic buildings. Three different displays — “explore” by Jonas Denzel, audio by Sören Schaudel; “Billiken” by Shkunna Stewart and Wills Glasspiegel; “Ba Boom Boom Pa Pop Pop” by Nick Cave — will be featured through September, all starting each night at 9pm. Each contemporary display is projected across the 2.5 acre facade of The Mart — making it both hard to miss and a can’t-miss.

222 Merchandise Mart Plaza 

The Northman Summer Music Series

In search of a solid venue for live music and great drinks in the city? Then your next stop needs to be The Northman, a beer and cider garden where fun drinks meet sweet tunes. Throughout the whole summer you can find a lineup of musicians from a range of genres — stay tuned to their event calendar to see what’s in store for this month.

233 E. Riverwalk

Rooftop Cinema Club

With locations in major cities like Los Angeles, New York and London, Rooftop Cinema Club promises “the ultimate open-air viewing experience” in Chicago’s Fulton Market area. If you’ve been holding back on going to movie theaters, this outdoor viewing room is an excellent opportunity to get back into the swing of catching flicks somewhere other than your living room. On the terrace of the Emily Hotel, there are deck chairs to relax in while watching iconic cult and classic movies — plus food and a full bar make this deal even better! For more information and a movie lineup, visit the RCC website.

311 N. Morgan St.

Shedd Aquarium Community Action Days

Photo courtesy of Shedd Aquarium

Want to do your part to help clean up the environment? The Shedd has you covered with a number of action days throughout the month of August. Specific clean up activities vary per day, as does the location. But no matter where you are in the city, you’re making a positive impact for your community. A comprehensive schedule and registration are available on the Shedd Aquarium website.

Evanston Starlight Movie Series

Enjoy your favorite Hollywood stars while sitting under the stars at Evanstons’s Starlight Movie Series, which runs all through August and into early October. Screenings include movies like Oscar-winning film King Richard and fan-favorites like The Blind Side. All showings begin at 7pm; in the event of bad weather check the Evanston Parks and Recreation Facebook page for updates or the Series’ website. Bring the family, bring some lawn chairs and enjoy this summer opportunity!

Grant Park Music Festival

Enjoy the hum of the city as you recline on an expansive lawn to witness all the wonder of live music and performance this series has to offer. From classical music to Cirque performances, this summer’s lineup will have a little something for everyone. And even if there isn’t a show to your liking, the atmosphere will more than make up for it. Tickets, stage locations and additional information can be found on the Festival website.

Alebrijes: Creatures of a Dream World

At Wheaton’s Cantigny Park they know what it means to make a dream into reality with their five-month exhibit dedicated to the truly fantastic world of folklore beasts. Alebrijes refers to “imaginary creatures that possess elements from different animals.” These creatures stand at around 15-feet tall, are vibrantly decorated and are sure to wow all visitors of any age. Information about the project and details on how to view them can be found on the Cantigny Park website.

1S151 Winfield Rd., Wheaton

Throwback Thursday Live Music at Tiny Tapp & Cafe

Hugh Too, a cover band, plays at Tiny Tapps | Photo courtesy of Tiny Tapps and Cafe

The Riverwalk downtown offers itself as a great venue for food, drinks and just enjoying the heartbeat of the city with spectacular views. To add to the atmosphere, Tiny Tapp & Cafe has added live music to their outdoor setting. Every Thursday through September 15, they will have various cover bands come and play from 6-8pm with the river as the backdrop to the show. Additional information can be found on the Tiny Tapp website.

55 W. Riverwalk South

The Devil Wears Prada 

The cut-throat side of the fashion industry is on display once again in The Devil Wears Prada — this time as a musical. Broadway in Chicago is revamping this fan-favorite storyline, with a creative team flush with big names such as Elton John and Anna D. Shapiro. Fans of the movie or anyone looking for an enthralling night of theatre needn’t look further than this performance — running through August 21.

24 W. Randolph St.

Winnetka Live Music Fridays

Winnetka is always finding new ways to bring the community together, and this summer is no exception. With weekly Friday concerts in the heart of town, everyone’s invited to join in the merriment. The event is first come, first serve so get down there early to grab a spot and some food and drink from Good Grapes. Dates this month include August 12, 19 and 26, entry fees vary.

821 Chestnut Ct., Winnetka

August 2: Jarrett Dapier: The Most Haunted House in America

The Book Stall will be hosting a spook-tacular evening with author Jarett Dapier as he unveils his latest book The Most Haunted House in America. Follow Dapier as he walks the audience through the macabre text and chill-inducing illustrations of America’s most haunted house — The White House. The evening will include a live drum line to accompany the reading, as well as food and drink for adults and children. More information can be found on The Book Stall’s website.

Good Grapes, 821 Chestnut Ct., Winnetka

August 3: Children’s Concert at Hubbard Woods in Winnetka

Looking to find a little summer fun for your kids? Then head over to Winnetka this month for the Children’s Concert at Hubbard Woods. There, kids and their families can enjoy an interactive concert, a splash pad zone and a picnic in the park with food for purchase from Hubbard Wood businesses. Admission is free but registration may be required for additional information, which can be found on the Winnetka Park District website.

939 Green Bay Rd., Winnetka

August 3: Highwood Margarita Night

The Highwood Margarita Night is about as close as you can get to a tropical vacation without having to go too far. Join Celebrate Highwood for a night of whimsical frozen beverages, tasty Mexican food and enough Jimmy Buffet-inspired ambience and music to really set the scene. Admission is free to this event that runs 4:30 – 9:30pm. More information can be found on the Highwood event page.

111 North Avenue, Highwood

August 4-7: Windy City Smokeout

BBQ, beer and bands — those three Bs are at the heart of the Windy City Smokeout. Enjoy the delicious food from various vendors, the endless selection of craft beverages and the entertainment from some of the world’s greatest country stars like Willie Nelson and Family and Tim McGraw. Check the Windy City Smokeout website for tickets and more information about this can’t miss festival at the United Center.

August 5-7: Festa Italiana Naperville

Festa Italiana Naperville attendees | Photo courtesy of StarEvents

All things Italian are happening in Naperville this August as they celebrate the Festa Italiana. Authentic food, beautiful music and Italian spirit will be alive at the fest that is welcome to all. Spend the day absorbing the culture and spend the night dancing away to tunes from the old country. Ticket prices vary, more information can be found on the Festa Italiana event page.

523 S. Webster St., Naperville

August 6-7: Northalsted Market Days


Celebrating its 40th consecutive year in what is formerly Boystown, the Northalsted Market Days is a weekend filled with live music, drag performances, 200+ vendors, food, drink and so much more. In Chicago’s most queer-friendly neighborhood, don’t miss the chance to publicly celebrate your Pride outside of June. All ages are welcome to this event. There is a suggested $15 donation fee for entry, more information can be found on the Northalsted Market Days website.

August 10: Taste of Andersonville

Andersonville continues its run as one of the city’s most vibrant and innovative neighborhoods, constantly introducing new and unique programming. This month, head to Taste of Andersonville as they rustle up some of the best food in the area for attendees to try — the selections are truly as endless as they are delicious. Ticket packages vary in price, visit the Andersonville Chamber of Commerce website for more information.

Downtown Andersonville, N. Clark St.

August 12: SUE the T.Rex Virtual Tour: SUE’s Unearth Day Party!

SUE in the new suite | Photo courtesy of the Field Museum | Photo by: Martin Baumgaertner

SUE the T. rex — a landmark of Chicago’s Field Museum — will be celebrating its 22nd “Unearth Day” with a fun, educational virtual event. Join the museum for an evening of fun facts, trivia and a Q&A with staff members where they will reveal little known facts about SUE’s discovery. The event is 5 – 6pm; admission is free but there is a suggested donation fee. Specific programming and registration can be found on the Field Museum’s website.

1400 S. Lake Shore Dr.

August 12 – 14: Retro on Roscoe

What has been dubbed a “Generation X haven” will include a weekend of classic tunes from various bands; some great food and drink; a classic car show; art vendors; and so much more. Get groovy with your community at this fest that takes up six blocks of Roscoe Village with three concert stages. The hits are sure to keep coming, don’t miss out on this thrill of the summer. There is a $10 suggested donation fee, additional information can be found on the Retro on Roscoe event page.

2000 W. Roscoe St.

August 13: 2022 Avondale Bar Crawl

Avondale is introducing its first-ever neighborhood bar crawl and inviting all locals to come and check it out. Enjoy four different bars over the course of four hours, where mingling and drinking are the name of the game. Join the other 80 individuals on the crawl, and make this a night to remember. Tickets are available on the MPCEvents website — bar crawl specifics will be emailed to attendees prior to the event.

August 14: Summer Float Party

Photo courtesy of Friends of the Chicago River

In an effort to spread the word about just how great the Chicago River can be, Friends of the Chicago River will be hosting a Summer Float Party. Float down the river and enjoy the sun and all the wonder Chicago’s natural resources have to offer. More information and specifics can be found on the FOTCR website.

August 16: Spotlight Garden Tours at Chicago Botanic Garden

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This series walks guests through the enormous grounds of CBG — including 28 gardens and four natural areas across 385 acres. Each event will be centered on a specific garden and encourages attendees to explore the depths of what is in the garden, how it is made and the benefits of maintaining them. Additionally, there is an event on August 30 if you cannot attend on the 16th. Those curious about the series can find information on pricing and select dates at the Chicago Botanic Garden website.

1000 Lake Cook Rd., Glencoe

August 17: Highwood Garlic Festival

The aroma of garlic in the air, can you think of anything more appealing? At the Garlic Fest in Highwood you are guaranteed an evening full of mouth-watering food, activities for the whole family, live music and a competition for best garlic dish. If you consider yourself a fan of the famous herb, do not hesitate to join the delicious fun from 4:30 – 9:30pm.

111 North Avenue, Highwood

August 19: Disco in the Park

Hosted by the Levy Senior Center in Evanston, this night of throwbacks will feature all the hits from the ‘70s. All ages are welcome to bring a blanket, a picnic and their groovy moves to this event that is sure to get people moving and shaking. Masks and social distancing are required  — more information can be found on the Evanston Parks and Recreation website.

300 Dodge Ave., Evanston

August 20: Oak Park Microbrew Review

Who doesn’t love having a cold one on a hot summer day? The 15th annual Oak Park Microbrew Review does too, so they are bringing it to the public this month with dozens of beer vendors from around Illinois. And as if that wasn’t reason enough to attend, this fest is the largest zero-waste craft beer festival in the Midwest — which means you’re actually doing your part for the environment by attending, right? Specifics can be located on the Fest’s event page.

100 N. Marion St., Downtown Oak Park

August 20: Carpe Librum Pop-Up Used Book Sale

If you still want to get in some summer reading, this pop-up event in Lakeview is a must-hit. From 11am – 12pm, peruse thousands of used books all of which cost $6 or less. All proceeds go to Turning the Page, which engages local North Lawndale families for the betterment of their child’s education.

3140 N. Southport Ave.

August 20: Run For Beer 

Photo courtesy of Illinois Brewery Running Series

Sure, you might enjoy running, but you have to admit it sounds a whole lot more fun when there is beer waiting for you at the finish line. Run For Beer — hosted by the Illinois Brewery Running Series — will take place at Cruz Blanca Brewery in the West Loop and offers each runner a free pint and some cool take-home swag at the end of the race, not to mention other family-fun activities. More information can be located on the Run For Beer event page.

904 W. Randolph St.

August 21: Roscoe Village ProchFest

Calling all music lovers, the Roscoe Village/Lakeview neighborhood has been hosting a PorchFest concert series — where local musicians from different genres set up on the porches of some of the neighborhood’s favorite houses and play their tunes. While the Lakeview event has already taken place, still on the horizon is the Roscoe Village concert — be sure not to miss this unique, musical event. Program specifics can be found on the Roscoe Village website; tickets are yet to be released.

Between Addison to Wellington and Ravenswood to Western

August 21: Andersonville Vintage Market

If you fancy a vintage find, head to the Andersonville Vintage Market, which includes more than 20 stores over the course of the weekend. There are only a few dates left this summer, so don’t miss your chance. See the lineup of participating stores on the Andersonville Chamber of Commerce website.

1500 W Catalpa, between Clark and Ashland

August 27: 2022 Chicago Summer Whisky Tasting

Whiskey lovers would be sour to miss this event, a three-plus hour tasting where sampling over 20 different whiskeys is the name of the game. What’s more, there will be a variety of food and live entertainment to seal the deal. Ticket prices vary depending on which package you choose, but either way, you’re guaranteed an evening of delicious sips and mingling amongst other spirit enthusiasts — and as a bonus, all designated drivers can get into the event for free. Specific programming and registration can be found on the 2022 Whisky Tasting event page.

2251 N. Lincoln Ave.

August 27: Thalia Hall Block Party

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Thalia Hall is well known around the city for its top-tier concert lineup every year, and now, they are bringing it to the community for their inaugural Thalia Hall Block Party. Enjoy outdoor sessions from six musical acts, with Thee Sacred Souls headlining the show. Additionally, enjoy some tasty bites and sips while perusing offerings from local vendors. There is a suggested $5 donation, with all proceeds going to the Pilsen Food Pantry — more details can be found on the Thalia Hall event page.

1807 S. Allport St.

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Margaret Smith is a Chicago-based writer and editor with a passion for socio-political storytelling about their community. They are a graduate of Columbia College Chicago.

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