The best things to do in Chicago this weekend

Find the best things to do in Chicago this weekend with our guide to concerts, exhibitions, festivals and more.
Photograph: Neal O'Bryan
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Those planes zooming by overhead can only mean one thing: It's Chicago Air and Water Show weekend, and you'll want to head to a beach or a rooftop for the best views of the stunts. If aerial maneuvers aren't your cup of tea, you can catch Drake at the United Center or Pearl Jam at Wrigley Field. Douglas Park hosts not one, but two, music festival this weekend, beginning with R&B lineup at the free Westside Music Festival on Saturday and concluding with the hip-hop-centric Lyrical Lemonade Summer Smash on Sunday. You can also drink interesting brews at Half Acre's Big North party, attend the Windy City West Indian Carnival in Hyde Park or pig out at BrunchCon. Check out all the best things to do in Chicago this weekend.

Things to do this weekend in Chicago

1
Drake
Photograph: Courtesy REX/Shutterstock
Music, Rap, hip-hop and R&B

Drake + Migos

icon-location-pin United Center
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After collaborating on "Walk It Talk It," Canadian R&B superstar Drake joins forces with hip-hop trio Migos on the Aubrey and the Three Migos Tour. While you shouldn't expect Drake to address the “The Story Of Adidon” diss track that Pusha-T released, you'll probably hear plenty of ubiquitous new tracks from his latest album Scorpion. Here's hoping that Drake and Migos play at least part of the show in their Soul Train-themed attire.

2
Half Acre Balmoral
Photograph: Nick Murway
Things to do, Festivals

The Big North

icon-location-pin Lincoln Square
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Half Acre Beer Company throws its annual bash at its expansive Balmoral Brewery, welcoming guests into its taproom, production space and patio to enjoy drinks, music and more. This year's festivities will feature samples of newly developed beers and music from local psych outfit Post Animal, indie rockers Dehd and dream pop act Divino Niño. Tickets include food, a glass, a koozie and first-come, first-served access to a variety of barrel-aged and Wyld Beers.

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3
French Toast at Jam
Photograph: Ken Carl
Things to do, Conventions

BrunchCon

icon-location-pin Bucktown
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Your favorite meal finally gets the convention it so rightly deserves, as 30 vendors serve up brunch bites, accompanied by open mimosa and Bloody Mary bars. During two separate sessions, guests will be able to explore the "Museum of Brunch," shop for supplies to take home in the BrunchCon market and play mimosa pong with friends. Like a great brunch, you'll wish you could do this every day of the week.

4
iO Theater
Photograph: Anthony Soave
Comedy, Improv

Bentwood Comedy Festival

icon-location-pin River North
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Named after the style of chair that is found on improv comedy stages throughout the city, iO Theater's 10-day fest celebrates improv, sketch and experimental comedy, with headlining performances from Jet Eveleth and Scott Adsit, local podcast Hello From the Magic Tavern, the writers behind Clickhole and Comedy Central's Jordan Klepper.

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5
Illinois State Fair
Things to do, Festivals

Illinois State Fair

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Come for the fried festival fare, stay for the Butter Cow—the fair's unofficial icon and Paula Deen's life-long dream, a life-size cow sculpture made of 500 pounds of butter. The annual State Fair features carnival rides, auto races, livestock competitions and (separately ticketed) concerts from the likes of Ludacris, 311, Foreigner and more. Really, there's no better excuse to make the trip to our state's capital.

6
Yayoi Kusama Infinity Mirror Room “Let’s Survive Forever”
Photograph: Courtesy wndr museum
Art, Installation

wndr museum

icon-location-pin West Loop
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Step inside one of Japanese artist Yayoi Kusama's famous Infinity Mirror Rooms at this new pop-up exhibition, which features installations that blend art and science. Other attractions include a “zero-gravity ball pit” that uses helium balloons and fans to simulate a weightless version of the childhood attraction, a three-story-tall kinetic sculpture and “edible experiences” designed by Toronto's Future Food Studio that transfor flavors into vapor. According to a press release, the exhibit will remain on display for a “limited, but undetermined, amount of time,” so you might want to book tickets sooner rather than later.

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7
Angie Stone
Photograph: Courtesy Westside Music Festival
Music, Rap, hip-hop and R&B

Chicago Westside Music Festival

icon-location-pin North Lawndale
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The annual Westside Music Festival returns, taking over a section of Douglas Park for a day of throwback R&B. Soul singer Angie Stone, who sang with Lenny Kravitz and was a member of ‘70s hip-hop trio the Sequence, headlines this year's festivities, joined by vocal groups Silk and 702, as well as a surprise Chicago artist. The festival is free, so pack a picnic basket, kick back and add some soul to your summer.

8
Pearl Jam
Photograph: Danny Clinch
Music, Rock and indie

Pearl Jam

icon-location-pin Wrigleyville
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The last time that Pearl Jam played Wrigley Field was during the season that ended with the Cubs winning the World Series for the first time in 108 years. We don't want to jinx anything, but we're going to interpret the Seattle rockers' return to the Friendly Confines as a good omen. No matter what happens, you're probably going to be subjected to a rendition of Eddie Vedder's schmaltzy Cubs anthem, "All the Way."

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9
Sangria Festival Chicago
Photograph: Courtesy Sangria Festival Chicago
Things to do, Festivals

Sangria Festival Chicago

icon-location-pin Humboldt Park
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Humboldt Park transforms into an outdoor tapas bar during this boozy bash, which pairs bites from local restaurants with pitchers of red wine and chopped fruit. Lay our a blanket to sip sangria on the lawn, put color on a canvas at the festival's painting station or watch flamenco dancers sway to Spanish music.

10
Music, Punk and metal

Bric-a-Brac Scummer Slam

icon-location-pin Logan Square
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The nostalgic record-slingers at Bric-a-Brac Records host another end of the summer party in the East Room's parking lot, outfitted with a lineup of punk acts from Chicago and beyond. This year's bill includes Detroit punk rocker Nikki Corvette, long-running local DIY outfit the Lemons, Florida punks Gino and the Goons, and Minneapolis noise-makers Royal Brat. Ethers, Color TV, Datenight, Bruised, Nude Model, Skull Cult and Dedpet are also on the lineup, with all donations benefiting the Goethe Elementary School music program.

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11
Edison Park Fest
Photograph courtesy of Edison Park Fest
Things to do, Festivals

Edison Park Fest

icon-location-pin Edison Park
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This street festival turns Edison Park into a giant carnival, complete with rides for the kids, magic shows, jugglers and an entire lineup of tribute bands.

12
Glenwood Avenue Arts Fest
Photograph: Al Goldberg
Things to do, Festivals

Glenwood Avenue Arts Fest

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The weekend artists' market in Rogers Park combines three stages of music and performance acts with locally made arts and crafts from more than 100 vendors. 

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13
Soul Summit
Photograph: Mo Manley
Clubs

Soul Summit

icon-location-pin Logan Square
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While it's been ousted from its longtime home at the Double Door, this killer monthly party lives on at East Room with dusty grooves and rare soul that will keep the dance floor packed until 5am. Resident DJs Scott "Sloppy White" Williams, Dave Mata, Duke Grip and Mo Manley invite crate-digging experts to show off their collections of vintage vinyl. In August, DJ Nu-Mark of Jurassic 5 is the special guest, spinning the funk and soul tunes that inspired his alt-hip-hop beats.

14
The U.S. Navy Blue Angels, Firebirds Delta Team and more perform aerial stunts at the Chicago Air and Water Show, August 16, 2014.
Photograph: Anthony Soave
Things to do, Festivals

Chicago Air and Water Show

icon-location-pin Lincoln Park
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Don't be surprised if you get a neck ache from looking up during this two-day event. Join throngs of people at North Beach and surrounding areas to catch air and watercraft demonstrations, including the U.S. Navy Blue Angels and the U.S. Army Parachute Team Golden Knights.

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15
lollapalooza 2017, joey bada$$
Photograph: Jaclyn Rivas
Music, Music festivals

Lyrical Lemonade Summer Smash

icon-location-pin North Lawndale
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Chicago hip-hop blog Lyricial Lemonade takes its annual summer concert outdoors this year, setting up in Douglas Park (the same park where Riot Fest is held). Joey Bada$$, Vic Mensa and Trippie Redd headline the Summer Smash, but the rest of the lineup will probably only look familiar to hardcore fans of Soundcloud rappers, including acts like Ski Mask the Slump God, Queen Key, Yung Bans and Lil Skies.

16
Windy City West Indian Carnival
Photograph: Courtesy Windy City West Indian Carnival
Things to do, Festivals

Windy City West Indian Carnival

icon-location-pin Hyde Park
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Follow the smell of sizzling Carribean food and the parade of brightly colored outfits to this Hyde Park event, which features steel pan music and a spirited masquerade band competition.

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17
Photograph: Courtesy the Field Museum
Things to do, Exhibitions

“Antarctic Dinosaurs”

icon-location-pin Museum Campus
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Our planet’s changing climate and geology is explored in this new exhibition, which displays newly-discovered fossils of dinosaurs who roamed Antarctica 200 million years ago—when the region was covered by a lush forest. Visitors will be able to follow the journey that Field Museum scientists took to make these discoveries while battling extreme weather on the South Pole.

18
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Photograph: Zach Weiss
Things to do, Festivals

Bristol Renaissance Faire

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Have a jolly olde time and butcher your favorite European accent as you engage in live-action fantasy play, enjoy interactive riddles, cheer on your favorite jousting knight or revel in period performances from 1574. The festival takes place Saturdays, Sundays and Labor Day in July, August and early September.

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