Chicago summer festivals guide

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
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.
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.
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.
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.
Bike the Drive
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.
Chicago summer festivals in June 2018
Chicago Gospel Music Festival
The city's annual celebration of gospel music welcomes national touring acts and up-and-coming local talent to Millennium Park for two days of uplifting songs and hymns. Lineup to be announced.
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.
57th Street Art Fair
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.
World Naked Bike Ride
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.
Taste of Randolph
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.
Chicago Pride Fest
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.
Country LakeShake Festival
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.
Ravenswood on Tap
The stretch of Ravenswood Avenue that calls itself "Malt Row" hosts this annual festival, which prominently features the neighborhood's diverse craft brewing scene. You'll find beer from Band of Bohemia, Begyle Brewing, Dovetail, Empirical, Half Acre and more, in addition to food from local restaurants and live music.
Randolph Street Market Festival
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.
Mamby on the Beach
If you can't afford a vacation to the ocean this summer, you can at least enjoy some music with sand beneath your toes at Mamby on the Beach. The lakefront festival takes place on Oakwood Beach, and typically features a mix of indie, electronic and hip-hop acts.
Chicago summer festivals in August 2018
Bristol Renaissance Faire
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.
Lollapalooza
Taking over Grant Park for four days each summer, Lollapalooza is Chicago's largest music festival, attracting an estimated 100,000 attendees each day. This year, the Weeknd, Bruno Mars, Jack White and Arctic Monkeys headline the fest, topping a bill that includes acts like St. Vincent, Franz Ferdinand, Tyler, the Creator and more. With more than 180 artists, grub from local eateries and plenty of beer, this is the kind of weekend that Chicago summers were made for. RECOMMENDED: Check out photos and reviews from Lollapalooza
Flashback Weekend Chicago Horror Convention
Let out a few blood-curdling screams during Flashback Weekend, an annual convention that celebrates gory slasher flicks, cinematic monsters and horror films. Confirmed guests at this year's event include Brad Dourif—better known as the voice of Chucky in the Child's Play film series. Of course, you'll also be able to dig through a terrifying amount of classic movie memorabilia or show off your creepiest outfit at a horror-themed costume contest.
Jeff Fest Arts and Music Festival
Grab your djembe and head to Jefferson Park, where a drum circle is just one of the many highlights of this annual community festival. This year's live music lineup is filled with homages to classic rock, including Pink Floyd tribute act Echoes of Pompeii, ZZ Top cover band Eliminator and Led Zeppelin devotees Kashmir.
Edge Fest
This is not a celebration of U2's guitarist, instead 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.
Illinois State Fair
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.
Chicago Hot Dog Fest
The Chicago History Museum organizes this celebration of one of the city's most famous dishes, serving creative franks from the likes of Byron's, Chicago's Dog House, Edzo's and more. While you're chowing down on neon green relish and sport pepper, you can listen to live music or attend a lecture that will teach you about the history of the Chicago-style hot dog.
Festival Cubano
Back in Riis Park, the three-day Festival Cubano brings together musician, dancers and food for a weekend of cultural celebration. Begin by checking out the festival's 30 Cuban vendors, who will be serving dishes such as jibarito sandwhiches, ropa vieja, lechón and tostones. Once you're full, play a game of dominos, shop for a hand-rolled cigar, watch boxing matches or catch a performance from Cuban stars like Willy Chirino and Jerry Rivera.
Retro on Roscoe
Antique vendors and classic cars fill six blocks of Roscoe Village at this throwback street market, where everything old is new again. The music lineup is equally nostalgic, featuring tribute acts like Too White Crew, Trippin Billies, American English and 16 Candles.
Ginza Holiday Festival
Celebrate Japanese culture, food and entertainment at the 63rd annual Ginza Holiday. Meet and buy crafts from master craftsmen (called Waza), who will be flown in from Tokyo to share their skills. Live martial arts, cultural songs, classical dances and Japanese food (teriyaki, sushi, Spam musubi, Hawaiian shave ice and more) give Chicago a taste of Japan.
Chicago summer festivals in September 2018
Chicago Jazz Festival
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 free concerts at the Chicago Cultural Center and Millennium Park. This year, the festivities expand to local music venues, where performers will play free shows from August 24 through 29. Headliners include composer, pianist and radio personality Ramsey Lewis; noted jazz vocalists Kurt Elling and Dianne Reeves; and funk legend Maceo Parker.
North Coast Music Festival
Celebrate Labor Day weekend in Union Park at North Coast Music Festival, where EDM once again dominates the lineup. Headlining acts include Swedish DJ duo Axwell Λ Ingrosso, French producer DJ Snake, electro-funk act Jamiroquai and sultry R&B singer-songwriter Miguel. You'll also be treated to DJ sets from local musicians (such as the Cool Kids and Sen Morimoto) and get to take in all of the attendees wearing rave-ready costumes.
Cider and Sliders Festival
Taste more than 30 ciders and enjoy some miniature burgers at the latest edition of this Lakeview Festival. The ciders and sliders are just two of the many attractions at the Labor Day weekend event, which also features two stages of music (provided by local cover bands) and a kids area. You'll need purchase a $35 ticket to attend the cider tastings, which take place during three sessions throughout the weekend.
Slow and Low Chicago Lowrider Festival
Hundreds of tricked-out cars and motorcycles line Loomis Street in Pilsen during this annual community festival, where you can take a look under the hood and watch classic rides bouncing around (with some hydraulic assistance). If you can tear yourself away from the automotive display, you can chow down on tasty tacos, shop for goods made by local vendors and listen to live DJs.
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.
German-American Oktoberfest
Grab a plastic stein and munch on a pretzel at this annual Lincoln Square celebration of Deutschland heritage. The street party takes place under two gigantic tents and features plenty of German food, music and dancing. Make sure to stop by to see the annual Von Steuben Parade march up Lincoln Avenue on Saturday at 2pm.
Festival de la Villita
Celebrate Mexico's independence from Spain with Mexican food, music and dancing in Chicago's Little Village neighborhood. Vendors and carnival rides fill the streets on all three days and on Sunday, the 26th Street Mexican Independence Day Parade ends here.
Windy City Wine Festival
Quaff a glass of vino near Buckingham Fountain and admire the Chicago skyline at this yearly shindig, which features more than 300 wines from around the world and discussions with sommeliers and chefs. Attendees can choose from one of two evening sessions, with food from Taco in a Bag, Wally’s Waffles and others.
The Birdhouse Festival
Independent electronic music label Dirtybird brings a carnival to the parking lot of the Journeymen Plumbers Hall, soundtracked by a stacked lineup of the label's DJs. Dirtybird head honcho Claude VonStroke headlines the miniature festival, joined by labelmates J. Phlip, Will Clarke, Ardalan, Christian Martin and more.
Renegade Craft Fair
That slight chill means it’s time to head to Wicker Park’s gigantic craft fair, where serious crafters from around the country to sell their handmade arts and wares,. Browse and buy prints, pottery, jewelry and other handmade goods from makers near and far, while enjoying food and drinks being peddled by local businesses and vendors.
Find even more things to do in Chicago
Find even more things to do in Chicago
Find the best things to do with our complete guide to the city, including the latest festivals, restaurant openings, holiday coverage and more