Grab a blanket and head to Millennium Park, where the Chicago Jazz Festival presents an incredible and totally free lineup of live concerts spanning a variety of jazz genres, including fusion, bop and cosmic shizz. Roscoe Mitchell and Wadada Leo Smith headline and hip-hop fusionist José James pays tribute to Billie Holiday on Friday. (Millennium Park, 55 N Michigan Ave, Fri–Sun noon–9:30pm. Free)
See the odd, the extraordinary and everything in between at the theater festival loved for (and possibly avoided because of) its lineup chosen through a lottery-based selection process. Buying a ticket for one of Chicago Fringe Festival’s performances is a gamble itself, but that’s the point. Things may get pretty weird, but that’s what makes Fringe freaky-fun. (Various venues across Jefferson Park, 4822 N Long Ave, Fri–Sept 13, $5 one-time button purchase, $10 per show, multi-show passes available)
As if this weekend wasn’t going to be hot enough, Chicago’s Best Summer WingFest cranks the temperature up with an all-you-can-handle fiery food festival. Admission gets you unlimited wings from local vendors, so prepare to come hungry and leave sweaty. (Chicago Journeymen Plumbers Union Hall, Bailey Auditorium Parking Lot, 1340 W Washington Blvd, Sat 1–7pm. $40, VIP $100)
4. Rally for one more summer music fest
We know you’re losing steam, and we know it won’t be painless. But we also know North Coast Music Festival’s top-tier lineup is worth the sweat and tears for any EDM, jam or rap lover. This year’s performers include the Chemical Brothers, D'Angelo, the Roots, Porter Robinson, Chromeo, Portugal. The Man, Tycho and Steve Aoki, so put on your freaky rave costume, paint your face like a neon animal and rally for one more sweltering, sticky music fest. (Union Park, 1501 W Randolph St, Fri–Sun noon. One-day pass $69, three-day pass $159, VIP $259)
Get a taste (or 15) of the emerging South Loop craft beer scene at the Motor Row Craft Beer & Wine Festival, where more than 20 Midwest breweries and wineries represent their suds and sauvignons, including Chicago’s own Vice District, Motor Row and Rude Hippo Brewery. Whether you’re a craft connoisseur seeking the next hip brew or just need an excuse to day-drink, get ready to raise a glass. Tastings run from 2 to 6pm. (Wabash Ave between 16th & 18th Sts, Sat & Sun 1–10pm. Free, tasting tickets $35)