Credit: The NBDY Design Co.


Third Annual 26th Annual Comedy Festival

The A.V. Club welcomes headliners Tracy Morgan and Sarah Silverman to town for its third annual comedy festival. Other performers include Reggie Watts, Jenny Slate, and Chris Gethard. Wed 6/1-Sun 6/5, various locations,, $10-$72.50.

Pilsen Food Truck Social
Pilsen Food Truck Social

Pilsen Food Truck Social

This festival features more than 20 local food trucks in one place—Da Lobsta, Pierogi Wagon, and Tamale Spaceship among them—with live music from Sonorama and CumbiaSazo, displays from local artist Kinga McCraven, and even more to eat from local brick-and-mortar restaurants, for those who prefer their food not on wheels. Sat 6/11-Sun 6/12: 10 AM-11-PM, 18th and Allport,, $5 suggested donation, $20 sampler tickets available.

Printers Row Lit Fest

The midwest’s largest book fair hosts panels, discussions, performances (musical and literary), and signings with guests like Marcia Clark, Seymour Hersh, Lindy West, and Ethan Hawke—plus some 200 others. Among this year’s highlights is the presentation of the Chicago Tribune Young Adult Literary Award to R.L. Stine. Some events require tickets. Sat 6/11-Sun 6/12: 10 AM-6 PM, Dearborn between Congress and Polk, 312-222-3986,, free.

Chicago Ale Fest

More than 200 beers from American craft breweries—plus live music and food from local eateries, including Burger Bar and Taco in a Bag. 6/17-6/18: Fri 6-10 PM, Sat 2-6 PM, Buckingham Fountain, 301 S. Columbus, 312-888-2104,, $50, $25 for designated driver ticket.

Pride Fest
Pride FestCredit: John J. Kim/Sun-Times

Pride Fest

A warm-up for the Pride Parade on Sunday, June 26, this Boystown takeover kicks off with a Pet Pride Parade, local street vendors, and three stages of music with performances by Dumblonde, Daya, and Jordin Sparks. Sat 6/18-Sun 6/19: 10 AM-10 PM, Halsted between Grace and Addison,, $10 suggested donation

Vegan Food and Drink Festival

A fest where all the food is 100 percent vegan—even the Big Mac, a new addition to this year’s edition. Other bites include vegan hot dogs, doughnuts, waffles, and more, with performances by a lineup of all-vegan artists. Sat 6/25, 11 AM-7 PM, Grant Park, 100 S. Lake Shore,, $10, $20 for VIP, free for children under 12.


Millennium Art Festival
Millennium Art FestivalCredit: Richard A. Chapman/Sun-Times Media

Millennium Art Festival

The free outdoor festival in the Loop showcases artwork by more than 100 artists. There’s also live music, plenty of food and drink, and an interactive graffiti wall for guests to work their own creative muscles. 7/8-7/10: Fri 11 AM-6 PM, Sat-Sun 10 AM-5 PM, Lake and Michigan,, free.

Roscoe Village Burger Fest

Enjoy some of Chicago’s best burger spots—including Butcher & the Burger, Fatso’s Last Stand, and Square Bar & Grill—all in one place, plus two live-music stages and a “Kid’s Zone” full of crafts and activities for the little ones. Sat 7/9-Sun 7/10: 11 AM-10 PM, Clybourn between Diversey and Barry, $10 suggested donation.

Bristol Renaissance Faire
Bristol Renaissance FaireCredit: Brian Schultz

Bristol Renaissance Faire

Transport back to Elizabethan England with more than 30 acres of 16th-century-themed games, rides, arts, crafts, food, and music. 7/9-9/5: Sat-Sun 10 AM-7 PM, Bristol Renaissance Faire, 12550 120th, Kenosha, Wisconsin,, $25, $11.50 for children 5-12, $125 season pass.

Chicago Hot Sauce Fest

For those who like things hot, this festival fires up pepper-eating and sauce contests, and vendors serve their spiciest sauces to only the most daring participants. Sat 7/23-Sun 7/24: noon, Belmont and Elston,, $5 suggested donation.

Fiesta del Sol

A Pilsen Neighbors Community Council fund-raiser known as the midwest’s largest Latino festival. There’s food from local vendors such as Juanita’s Mexican Food, Restaurant El Asador, and Taqueria La Ciudad; live music from Orgullo Guerrerense and Grupo Ideal de Tlapehuala Guerrero; educational resources like the Civil Rights of Immigrants Booth; and plenty of carnival rides (tickets required). 7/28-7/31: Thu 5 PM-10 PM, Fri-Sat 11 AM-11 PM, Sun 11 AM-10 PM, 1400 W. Cermak,, free.

Newberry Book Fair

Peruse more than 120,000 donated books, many priced at $3 or less. All proceeds benefit the Newberry Library. 7/28-7/31: Thu-Fri noon-8 PM, Sat-Sun 10 AM-6 PM, Newberry Library, 60 W. Walton, 312-255-3501,, free.


Retro on Roscoe
Retro on RoscoeCredit: Erin Nekervis

Retro on Roscoe

A street fest with three stages of live oldies music, a classic car and motorcycle show, and plenty of food and drink. 8/12-8/14: Fri 5-10 PM, Sat-Sun noon-10 PM, Roscoe and Damen,, $10 suggested donation.

Clark After Dark

The USO of Illinois hosts this one-night festival, which features local cover bands, military-themed activities and games, and a raffle. Thu 8/18, 5-10 PM, Hubbard between Clark and LaSalle,, $10, $100 VIP.

Festa Italiana

The four-day festival focuses on Italian fare, and takes place in the heart of Little Italy. There’s live music, a meatball-eating contest, and a dance ensemble performing and teaching the tarantella. 8/18-8/21: Thu-Fri 5-10 PM, Sat noon-11 PM, Sun noon-10 PM, Taylor between Ashland and Racine,, $5 suggested donation.

South Shore Summer Festival
South Shore Summer FestivalCredit: Eric Allix Rogers

South Shore Summer Festival

The one-day fest includes local food and drink along with dance performances and music from the storied house collective Chosen Few DJs. Sun 8/21, 11 AM-8 PM, South Shore Cultural Center, 7059 S. South Shore, 773-256-0149,, free.

Bucktown Arts Fest

This annual street fest, which supports arts education, boasts beer, food trucks, three stages of live music, more than 200 artists, and activities for kids. Sat 8/27-Sun 8/28: 11 AM-7 PM, Holstein Park, 2200 N. Oakley, 312-742-7554,, free.

Chicago Fashion Fest

New styles from the chicest boutiques come to Wicker Park. The weekend includes live music, an “after dark” fashion show, and deals at local stores. Sat 8/27-Sun 8/28: noon-10 PM, Damen and Division,, $5 suggested donation.

Taste of Greektown
Taste of GreektownCredit: Adrian Novak/FlickR

Taste of Greektown

A celebration of Greek culture in—where else?—Greektown. There’s lots of food, drinks, and dancing—all Greek, of course. Sat 8/27-Sun 8/28: noon-11 PM, 400 S. Halsted,

West Town Hoedown

A new street festival featuring an oyster-shucking contest, a shrimp boil, pie-eating contests, and live music. Sat 8/27-Sun 8/28: 11 AM-10 PM, Milwaukee between Division and Noble, $5 suggested donation.  v