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Everything You Absolutely Must Do in Chicago This Summer

Updated On 06/09/2017 at 04:23PM EST Updated On 06/09/2017 at 04:23PM EST
Everything You Must Do In Chicago This Summer
Lollapalooza | Paulino Afonso
June
Chicago Ale Fest
Chicago Ale Fest

June

Thursday
Jun 15
Various locations
From breakdancing battles and body-painted ping-pong to pop-up barber shops and blacklight murals, you never know what to expect when the Chicago Loop Alliance takes over select Downtown alleys at various dates this summer. The series starts with an urban rec room/playground at the Sullivan Center Alley and runs through September. RSVP beforehand for a free drink ticket.
Wednesday - Saturday
Jun 21-24
Various locations
Check out stand-up, storytelling, and sketches from a variety of comedians -- all of whom were told they weren’t good enough for other comedy festivals -- at this multi-day showcase at Zanies and Under the Gun Theater. Fans can vote on who will be back for the final night’s “Best of The Fest!” performance.
Friday - Saturday
Jun 23-24
Grant Park
This semi-annual beer fest is held at the same spot as Lolla, offering 200-plus brews served alongside live music and a mouthwatering lineup of food trucks like Sausage Fest and The Slide Ride.
Saturday - Sunday
Jun 24-25
Oakwood Beach
Is there a better way to spend a weekend than at a music festival on a beach? This year’s South Side indie dance party features MGMT, Local Natives, Cut Copy, Walk the Moon, and Flying Lotus.
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Courtesy of the Park at Wrigley
July
Pitchfork Music Festival
Pitchfork Music Festival

July

Thursday
Jul 6
Ravinia
It’s always a treat to see the local blues legend on a stage outside of his usual South Loop digs. But really, it doesn’t matter who you see at Ravinia this summer, just as long as you see someone at Ravinia this summer. The outdoor festival runs through September and features shows by Tony Bennett, Blondie, Andrew Bird, and dozens of others.
Friday - Sunday
Jul 14-16
Union Park
This year’s Pitchfork Fest lineup is one of the more impressive and eclectic in recent memory, with acts ranging from LCD Soundsystem and PJ Harvey to A Tribe Called Quest and Ride.
Friday - Sunday
Jul 14-16
560 W. Grand Avenue
Featuring a baker’s dozen of the finest pitmasters in America -- including local boys Smoque and Lillie’s Q -- plus live bands and an abundance of craft beer, it’s hard to find any faults with this annual BBQ throwdown.
Monday - Thursday
Jul 24-27
Wrigley Field and Guaranteed Rate Field
This year’s four-day Cubs-White Sox matchup features two day games in the Friendly Confines followed by two night games on the South Side, just as the baseball gods intended.
Thursday - Saturday
Jul 27-29
Lake Michigan Playpen
If you’re planning to be out on the Playpen boating like Diddy this year, this is the weekend to do it. In addition to bikinis and beats, hit the clubs for afterparties if you can’t didn’t enough of the daytime debauchery.
Friday
Jul 28
Lacuna Artist Loft
At the Bites & Booze Fest, themed “alcohol houses” take over three floors of a Pilsen arts loft with beer, whiskey, and tequila paired with meals from local restaurants. There’s also a rooftop party, cigar lounge, and “mixology stage,” whatever that means.
Saturday
Jul 29
Huntington Bank Pavilion
This year’s Tour de Fat has gone a bit mainstream with The Roots performing in a much larger venue than usual, but hopefully that won’t put a damper on the unclassifiable weirdness that is this annual booze-fueled bike-riding circus.
August
Lollapalooza
Lollapalooza

August

Thursday - Sunday
Aug 3-6
Grant Park
Lollapalooza is a four-day gig now, so plan to wade through a sea of humanity at North America’s largest festival and run into at least three randoms from high school. Chance the Rapper, Arcade Fire, The Killers, and Lorde are among the top-billed acts.
Sunday
Aug 6
Pilsen
Yes, it’s a lowrider festival. Watch tricked-out cruisers parade through Pilsen with a pop-up market, mariachis, and thousands of other car and motorcycle enthusiasts from around the country.
Friday - Sunday
Aug 11-13
Chicago History Museum
The illustrious Chicago hot dog gets its own three-day festival, jam packed with crazy encased-meat creations and, believe it or not, presentations from hot dog historians. No ketchup allowed.
Friday - Sunday
Aug 11-13
North Avenue Beach
It’s time to cram into North Avenue Beach and watch the Blue Angels pilots and Golden Knights parachute teams perform their stunts. If you’re smart, you’ll find your way onto a boat and watch the action on the water.
Wednesday - Sunday
Aug 30-Sep 10
Various locations
Jefferson Park becomes a hotbed of weirdness for this annual smorgasbord of delightfully off-kilter theater and comedy acts performing in venues around the neighborhood.
September
Riot Fest
Flickr.com/Covert Nine

September

Friday - Sunday
Sep 1-3
Union Park
There’s always a good time to be had at this eclectic Labor Day music party in the park, with this year’s acts ranging from Deadmau5 and Eric Prydz to Ween and Damian Marley.
Friday - Sunday
Sep 15-17
Douglas Park
Chicago’s annual punk-rock carnival is one of the best weekends of the year, with this edition featuring an all-star cast including Nine Inch Nails, Queens of the Stone Age, Wu-Tang Clan, and M.I.A.