International Mr. Leather

This Chicago institution is heavy on the parties, augmented by events like a “pecs and personality contest,” and capped by the crowning of a new International Mr. L. The popular vendor market, featuring all manner of leather and fetish gear, has a suggested $10 donation; to attend the rest you’ve got a choice between, er, packages: classic ($190) and premium ($225).

5/21-5/25: Thu 6 PM-1 AM, Fri-Sat 10-2 AM, Sun-Mon 10-4 AM, Congress Plaza Hotel and Convention Center, 520 S. Michigan, 800-494-8497,

57th Street Art Fair

Featuring more than 200 artists working in a variety of mediums, plus artist talks, live demos, and activities for kids. Sculptor Michael Imes receives this year’s 57th Street Art Fair Newcomer’s Award; see his work alongside pieces by Kathleen Eaton, Jim Bachor, and Mary Burke.

Sat 6/6, 11 AM-6 PM, and Sun 6/7, 10 AM-5 PM, 57th between Kenwood and Woodlawn, free.


Celebrating its 50th anniversary, this Andersonville street fair is possibly the only place in the world where you can get a glogg slushie—plus the usual riot of food, drinks, and live music.

6/12-6/14: Fri 5-10 PM, Sat-Sun 11 AM-10 PM, Clark between Catalpa and Balmoral, $10 suggested donation.

Fiestas Puertorriqueñas

Live music, art, carnival rides, and tons of Caribbean food. The Puerto Rican People’s Parade steps off at Division and Western Sat 6/20 at 2 PM, so get your flags ready.

6/18-6/21: Thu-Fri 3-10 PM, Sat-Sun noon-10 PM, Humboldt Park, 1440 N. Sacramento, 312-742-7549,

Tour de Fat

New Belgium Brewing’s whimsical traveling party returns again to Chicago, celebrating “bikes, beer, and bemusement.” Things kick off with a costumed bike parade. Notable brews on tap: Cocoa Mole chocolate porter, La Folie sour brown ale, and Carnie Blood, a blood orange saison.

Palmer Square Park, 3100 W. Palmer, 773-782-9471,, free.

Roscoe Village Burger Fest

Burgers from all your favorite spots, including Rockit Burger Bar, Trenchermen, Red Door, and Fork, plus music by I Fight Dragons, the Smithereens, the Polkaholics, and Catfight.

Sat 7/11-Sun 7/12, 11 AM-10 PM, Belmont between Damen and Oakley,, $10 suggested donation.

Chinatown Summer Fair

Traditional dance and music, martial arts demonstrations, food from neighborhood restaurants, a petting zoo, and a “hot legs” contest for men. One of the highlights every year is the lion dance procession.

Sun 7/19, 10 AM-8 PM, Cermak and Wentworth,, free.

Ginza Holiday Festival

This 60th annual Japanese fest features martial arts demonstrations and dances, calligraphy and exhibits by Waza artisans, and traditional Japanese food.

8/7-8/9: Fri 5:30-9 PM, Sat 11:30 AM-9 PM, Sun 11:30 AM-6 PM, Midwest Buddhist Temple, 435 W. Menomonee, 312-943-7801,, $7 suggested donation.

Northalsted Market Days

Touted as the largest two-day street fest in the midwest, NMD features Boystown vendors of arts, crafts, food, and drinks, plus live music. More than 150,000+ visitors attended last year.

Sat 8/8-Sun 8/9, 11 AM-10 PM, Halsted between Belmont and Addison,, $10 suggested donation.

Skokie’s Backlot Bash

Why not pay a visit to one of the only suburbs accessible via the CTA? This has a carnival, a car show, classic movies, and live music. The headliners are the Fabulous Thunderbirds, the Psychedelic Furs, and Tributosaurus performing music by the Cars.

8/28-8/30: Fri 6 PM, Sat 11 AM, Sun 8 AM, Oakton between Lincoln and Laramie, Skokie,, free.