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Chicago summer festivals guide

Start making weekend plans filled with food, music and art with our guide to Chicago summer festivals and street parties

Photograph: Jaclyn Elizabeth Rivas

Once the weather in Chicago starts warming up, the streets fill with people and the city's summer festival season gets started. Looking for things to do this weekend? May through September, there’s more than likely a festival for that. Whether you want to dance the night away to live music, hunt down the most impeccable burger in Chicago or taste as many local brews as possible, these summer fests have something for you. Don't get too stuffed though, because these Chicago summer festivals offer some of the best, and most worldly food available all year long. So what’re you waiting for?

RECOMMENDED: Things to do in the summer in Chicago



Chicago summer festivals in May 2018

Kids and Kites Festival

Recommended

Celebrate the arrival of spring at this free, outdoor family-friendly festival at Cricket Hill in Lincoln Park, where kids can fly a kite or watch professional demonstrations. Free paper kites will be provided, but families will also be able to purchase more intricate flying creations from a variety of vendors.

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Montrose Harbor , Uptown Saturday May 5 2018

Lincoln Park Wine Fest

Sample more than 100 wines from all over the world while listening to classical music at the second annual Lincoln Park Wine Fest. Yes, it doesn't get much more sophisticated than this. Our advice? Cozy up to the most nicely dressed person in attendance and ask them to take you for a post-fest ride on their yacht.

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Jonquil Park , Sheffield & DePaul Saturday May 19 2018 - Sunday May 20 2018
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Skokie Festival of Cultures

Take a tour of the world at this popular festival in Skokie, which features ethnic music, dance, food and arts. Attendees won't have trouble finding ways to celebrate cultural diversity at this free event, with activities like an international beer tasting competition and plenty of games for kids and families.

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Oakton Park , Skokie Saturday May 19 2018 - Sunday May 20 2018

International Mr. Leather Weekend

Rooted in a 1979 bar contest, this four-day event features parties, a fetish and leather market, a physique competition, a sexy shoe-polishing competition and, of course, the annual crowning of International Mr. Leather. In additional to the daily Leather Market, there are the big evening events: the Opening Ceremonies, Physique Competition, International Mr. Leather Contest, IML Victory Celebration Party, and the Black and Blue Ball. 

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Various venues , Loop Thursday May 24 2018 - Monday May 28 2018
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Bike the Drive

Recommended

Have you ever dreamed of cruising down Lake Shore Drive on your bicycle? Bike the Drive makes that dream a reality for one day this year, closing down the popular lakefront thoroughfare to cars early on a Sunday morning. Participants can bike from Bryn Mawr Avenue to the Museum of Science industry (and back) during the five hours of car-free riding.

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Bike the Drive Route , Edgewater Sunday May 27 2018

Randolph Street Market Festival

Recommended

More than 200 vendors hawk their antique housewares, furniture, ephemera, clothing and more at this indoor-outdoor festival. Stop in for vintage clothes and jewelry, a vinyl swap meet, a fancy food market and global goods bazaar or bring your own items for appraisal. This event typically occurs on the last weekend of each month. During the warm-weather months of May–September, the market adds an outdoor area, offering even more vintage shopping and a beer garden.

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Plumbers Hall Until Sunday April 29 2018
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Chicago summer festivals in June 2018

57th Street Art Fair

Recommended

The oldest juried craft fair in Hyde Park features paintings, sculptures, jewelry and ceramics from more than 200 artists. The event features pop-up artist talks as well as an artist-at-work area, where attendees can observe the process of creation. Attendees can shop for artwork created in a variety of mediums, including glass, jewelry, leather, photography, printmaking, painting, sculpture, wood, ceramics or fiber.

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57th St between Kenwood and Kimbark Aves Saturday June 2 2018 - Sunday June 3 2018
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Ribfest Chicago

Recommended

Head to North Center to dig into more than 50,000 pounds of ribs and BBQ and don't forget to grab some napkins. The annual celebration of saucy pork plays host to RibMania, the Midwest's only sanctioned rib-eating contest, which invites amateur and professional competitive eaters to chow down for a cash prize. 

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Lincoln Avenue / Irving Park Road / Damen Avenue Friday June 8 2018 - Sunday June 10 2018

CAKE: Chicago Alternative Comics Expo

For readers of independent comics and small press publications, there's no event more sweet than CAKE (short for the Chicago Alternative Comics Expo). Each year, the convention brings creators and fans to the Center on Halsted for two days of panels, workshops and, of course, shopping. 

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Center on Halsted , Lake View Saturday June 2 2018 - Sunday June 3 2018
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Spring Awakening Music Festival

Recommended

Chicago's largest EDM festival returns each June, armed with some of the biggest DJs and electronic acts in the world. The fest takes up residence in Addams/Medill Park—an upgrade (in terms of space and aesthetics) from the somewhat cramped confines of the event's former home in Soldier Field. The lineup typically includes an array of electronic heavyweights, and will be announced in the spring. 

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Addams/Medill Park , Little Italy, UIC Friday June 8 2018 - Sunday June 10 2018

Chicago Blues Festival

Recommended

Chicago honors its history as a destination for musicians by hosting the largest free blues festival in the world, bringing living legends and local 12-bar players to Millennium Park. Attendees can sit on the lawn to watch mainstage sets at Pritzker Pavilion or check out smaller acts slinging riffs on a handful of side stages. The 2018 lineup hasn't been announced yet, but the Chicago Blues Festival typically presents a thoughtful mix of contemporary and classic performers throughout the three-day event.    

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Millennium Park | Chicago, IL , Millennium Park Friday June 8 2018 - Sunday June 10 2018
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World Naked Bike Ride

Recommended

The annual clothing-optional bike ride takes over the streets of Chicago, attracting hundreds of scantily clad riders who help raise awareness about cyclists and positive body image. Check-in for the ride begins at 6pm in the West Loop and the ride usually runs from 8pm-11pm—for specific route details (typically announced the day of the event) check ChicagoNakedRide.org.

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Various venues , Loop Saturday June 9 2018

Taste of Randolph

Recommended

In the heart of restaurant row, on the same streets as some of Chicago's (and America's) best-known restaurants, this West Loop fest boasts six blocks of food, drink and music. Lineup to be announced. 

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Randolph St , West Loop Friday June 15 2018 - Sunday June 17 2018
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Chicago Pride Fest

Recommended

Prep for the following weekend's annual Pride Parade with Chicago's LGBT community at this celebration. The event offers musical entertainment and food and drinks from local vendors, right in the heart of Boystown. 

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Halsted and Roscoe Sts , Boystown Saturday June 16 2018 - Sunday June 17 2018

Country LakeShake Festival

Recommended

For country music fans in Chicago, there's no bigger event than the Country LakeShake Festival on Northerly Island. Headliners at this year's fest include The Voice judge (and Sexiest Man Alive, according to People magazine) Blake Shelton, singer-songwriter Dierks Bentley and bro-country duo Florida Georgia Line. In a city where most festivals tend to ignore country music, this is the hootenanny that Nashville devotees have been waiting for.

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Huntington Bank Pavilion , Downtown Friday June 22 2018 - Sunday June 24 2018
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Chicago summer festivals in July 2018

Windy City Ribfest

Recommended

Flex your jaw muscles and stretch that waistline at this 'cue fest in Uptown during Fourth of July weekend. Expect plenty of ribs and some live music, including national acts and regional cover bands. 

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Lawrence Ave at Broadway , Uptown Friday June 29 2018 - Sunday July 1 2018
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Fourth of July Fireworks

Recommended

The city of Chicago ditched its official fireworks show a few years back, but Navy Pier picks up the slack with its explosive Independence Day celebration. Revelers can head down to the pier or Millennium Park for an up-close view, but if you're not a fan of crowds you'll want to hit the lakefront or find a friend with a rooftop by the shore.

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Navy Pier, Gateway Park , Streeterville Wednesday July 4 2018

Taste of Chicago

Recommended

Since 1980, Grant Park has been hosting what has become the granddaddy of food festivals. You know the drill: Trade tickets for a taste of Chicago's street fare. Hopefully what you gain in weight, you'll lose from your wallet. As always, there will be music at Petrillo for you to listen to while you devour your turkey leg, Eli's Cheesecake or deep dish pizza. Vendor lineup to be announced.

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Grant Park | Chicago, IL , Millennium Park Wednesday July 11 2018 - Sunday July 15 2018
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Windy City Smokeout

Recommended

The annual celebration of grilled meats and country music returns to River North with ample amounts of pork, beer and tunes from some of country's biggest stars. Attendees will be able to sample smokey culinary creations from various local barbecue restaurants while licking sauce from their fingers.

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560 W Grand St , River West/West Town Friday July 13 2018 - Sunday July 15 2018

West Fest

Recommended

Befitting its location on the hip Chicago Avenue corridor, West Fest can be counted on for a great sleeper of a summer street fest bill. Occuring the weekend before Pitchfork Music Festival, it's a great way to ease into the summer festival mindset without having to purchase a pricey wristband. 

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Chicago Ave between Wood St and Damen Ave , Evanston Friday July 6 2018 - Sunday July 8 2018
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Roscoe Village Burger Fest

Recommended

It's no secret that we unabashedly love burgers, so you can imagine how much we're anticipating Roscoe Village's annual celebration of succulent, beef patty cuisine. Loosen your belt and prepare to taste grilled creations from local restaurants while enjoying live music and ample libations. 

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Belmont and Damen Aves , North Center Saturday July 14 2018 - Sunday July 15 2018

Bristol Renaissance Faire

Recommended

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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Bristol Renaissance Faire Saturday July 7 2018 - Monday September 3 2018
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Southport Art Festival

The Southport Corridor hosts its annual two-day art festival, bringing together a variety of artists and local vendors near neighborhood landmarks like the Music Box Theatre. Guests can peruse pieces, shop at Southport Avenue stores or get up early and enjoy the annual Gospel Brunch on Sunday morning.

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Southport Ave and Addison St , Lake View Saturday July 14 2018 - Sunday July 15 2018
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Chicago summer festivals in August 2018

Bristol Renaissance Faire

Recommended

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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Bristol Renaissance Faire Saturday July 7 2018 - Monday September 3 2018

Edge Fest

Not a celebration of U2's guitarist. The "edge" here is Edgewater. This year, the 'hood hosts a long weekend of wholesome family entertainment featuring tons of interactive, kid-friendly activities including karaoke night. Vendors willl serve up the anticipated array of festival foods (corn dogs, funnel cakes, blintzes, donuts), while local artists display handmade goods and crafts.

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Broadway from Thorndale to Ardmore Saturday August 4 2018 - Sunday August 5 2018
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Lollapalooza

Recommended

Taking over Grant Park for four days each summer, Lollapalooza is Chicago's largest music festival, attracting an estimated 100,000 attendees each day. If you're lucky enough to score a wristband, prepare yourself for headlining sets from some of the biggest names in pop, rock and electronic music. The 2018 lineup has yet to be announced, but there'll probably be at least one band you want to see among the 150+ acts that perform at the annual mega-fest. 

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Grant Park | Chicago, IL , Millennium Park Thursday August 2 2018 - Sunday August 5 2018
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Northalsted Market Days

Recommended

Northalsted Market Days is the largest two-day street festival in the Midwest and features lots of booze, phallic junk food (think corn dogs and chocolate-dipped bananas), music acts and terrific street fashion.

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Halsted and Roscoe Sts , Boystown Saturday August 11 2018 - Sunday August 12 2018

Illinois State Fair

Recommended

Come for the 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. Watch tractor pulls, horse races, parades and musical acts. Some events require additional tickets.

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Illinois State Fairgrounds Thursday August 9 2018 - Sunday August 19 2018
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Festival Cubano

Back in Riis Park for a seventh year, the three-day Festival Cubano brings together musician, dancers and food for a weekend of cultural celebration. See sets from Cuban musicians, enjoy carnvial and animal rides, enter the domino tournament or enjoy a hand-rolled cigar.

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Riis Park , Belmont Cragin Friday August 10 2018 - Sunday August 12 2018

Glenwood Avenue Arts Fest

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. The festival kicks off on August 14 with the Friday Night Cobblestone Jam.

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Glenwood Ave Friday August 17 2018 - Sunday August 19 2018
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Edison Park Fest

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.

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Edison Park , Edison Park Friday August 17 2018 - Sunday August 19 2018

Chicago Air and Water Show

Recommended

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, typically, the U.S. Navy Blue Angels and the U.S. Army Parachute Team Golden Knights.

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North Avenue Beach , Lincoln Park Saturday August 18 2018 - Sunday August 19 2018
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Chicago summer festivals in September 2018

Chicago Jazz Festival

Recommended

Chicago may be best known for its blues musicians, but these days it's more of a jazz city. The annual Chicago Jazz Festival celebrates contemporary improvisers and legendary players with four days of free concerts at the Chicago Cultural Center and Millennium Park. The festivities typically include tributes to notable jazz figureheads, an influx of international acts and visits from musicians who got their start in Chicago's jazz scene.

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Millennium Park | Chicago, IL , Millennium Park Thursday August 30 2018 - Sunday September 2 2018

Taste of Polonia

Feast on potato pancakes, kielbasa, pierogi and more at this Polish celebration during Labor Day weekend. After you've stuffed yourself, dance to some polka music, watch a cover band or play a few rounds of bingo.

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Copernicus Center , Jefferson Park Friday August 31 2018 - Monday September 3 2018
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North Coast Music Festival

Recommended

The other big festival in Union Park (the one that doesn't rhyme with Itchpork) leans heavy on EDM, jam and rap. Booked by some of the same folks behind Spring Awakening and Mamby on the Beach, North Coast offers up a mix of hip-hop and EDM acts.

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Union Park , West Loop Friday August 31 2018 - Sunday September 2 2018

Riot Fest

Recommended

It's the social event of the season for anyone with a denim jacket covered in patches hanging in their closet. Riot Fest brings punk, metal, indie acts to Douglas Park, setting up stages amid circus attractions, games and a sideshow. The 2018 lineup has not yet been announced.

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Douglas Park , North Lawndale Friday September 14 2018 - Sunday September 16 2018
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German-American Fest

Recommended

Grab a plastic stein and munch on a pretzel at this annual Lincoln Square celebration of Deutschland heritage. The street party features plenty of German food, music and dancing as well as the Von Steuben Parade on Saturday at 2pm.

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Lincoln Square , Lincoln Square Friday September 7 2018 - Sunday September 9 2018

Edgewater Fall Art Fair

Children's art and creativity come with a hyperlocal focus at the 3rd Annual Edgewater Fall Art Fair. Local schools showcase student artwork programs through gallery exhibitions, while smaller-size budding Rembrandts can face- and finger-paint at the Children’s Activity Corner. This family friendly fest includes a children's music talent showcase, costume contest, pet parade. Adults can enjoy the beer garden as well.  

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Granville El , Edgewater Saturday September 22 2018 - Sunday September 23 2018
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Chicago Gourmet

Recommended

The annual three-day fest kicks off Friday with its Hamburger Hop throwdown. Walk in to Millennium Park and waddle out once you've stuffed your face at cooking demos, tasting pavilions and a wine sampling. The 2018 vendor lineup has not yet been announced.

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Millennium Park | Chicago, IL , Millennium Park Friday September 28 2018 - Sunday September 30 2018

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