Chicago summer festivals in May 2018
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.
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.
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.
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.
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
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.
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.
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.
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.
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.
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.
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.
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.
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.
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 July 2018
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.
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.
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.
This riverfront bash offers samples of dishes from trendy area restaurants like Farmhouse, Taco Joint and El Hefe in addition to great view of the skyline. The shindig also includes a family fun area and live music.
Foamy, flat macrobrewed suds in a plastic cup not exactly your idea of a good time? Unleash your inner sophisticate at this Lincoln Park fest, which serves up more than 70 local, regional and national craft beers from 35 brewers. Purchase tickets before making your way to the tasting session each day from 11:30am–4pm—each ticket is good for one 3 ounce sample of beer. Once you've got a buzz going, admire some lawns or catch a band at the nearby Sheffield Music Festival and Garden Walk.
Chicago summer festivals in August 2018
The world's largest and oldest African-American parade enters its 89th year celebrating Chicago's youth. The parade's two-mile route begins in the Bronzeville neighborhood and continues north on Dr. Martin Luther King Drive, concluding in Washington Park with a picnic that features vendors and performers.
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.
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 with the Friday Night Cobblestone Jam.
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.
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.
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.
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.
It might sound like a Harry Potter convention, but Wizard World is an event that celebrates every facet of pop culture, including comic books, film and television. A convention center in Rosemont hosts the annual gathering, where attendees can line up for autographs or shop for merchandise amid a sea of vendors. Special guests at Wizard World Chicago Comic Con include Sebastian Stan (Bucky Barnes in the Captain America films), Dave Bautista (Drax in Guardians of the Galaxy) and Nichelle Nichols (Uhura in Star Trek).
Enjoy the feta, tzatziki, roasted chicken and more signature Mediterranean flavors at this two-day festival in Greektown, which offers tasty dishes cooked by some of the neighborhood's most beloved restaurants. The weekend also included live music and activities for kids.
The Food Truck Social brand has expanded to Logan Square, so brace your stomachs. With a lineup of more than 25 mobile eateries, music programmed by the Empty Bottle and the ability to purchase a $20 sampler ticket (which will get you dishes from any six trucks), you'll have no problem finding your new favorite spot to grab lunch. Sample grub from 5411 Empanadas, Churro Factory, Pierogi Wagon and more, then stick around for sets from electronic artist Prefuse 73, punk rockers the Men and experimental act Palm.
Chicago summer festivals in September 2018
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.