With the Cubs playing the way they’re playing, there’s a lot to get excited about this fall. But let’s not get ahead of ourselves. Let’s focus on the things we can actually control and depend on, like this immaculately curated roundup of the 20 finest events taking place in the best season to live in Chicago. If only it could last a couple months longer.
September
Lobsters Navy Pier
American Lobster Fest at Navy Pier | Flickr/Dan Dickinson

September

Thursday - Sunday
Sep 1-11
Jefferson Park (various locations)
With 50 troupes showcasing 200 performances in everything from comedy and drama to musicals and puppet shows, see the best in emerging storefront theater in venues and nontraditional locations around Jefferson Park including churches, cafes, and parks. If it’s weird, it’s here.
Friday - Sunday
Sep 2-4
Union Park
Chicago’s most nonjudgmental fest returns this Labor Day weekend and whether you’re into the bombastic EDM of Bassnectar, the jam-heavy guitars of Umphrey’s McGee, the out-there hip-hop of Action Bronson, or the ballsy rock of Sleigh Bells, it’s all good bro. Bonus: afterparties in local clubs and on hotel rooftops.
Friday - Sunday
Sep 2-4
Navy Pier
Navy Pier gets a bad rap (mostly by us), but there are ways to make it better. Like this annual celebration of all things lobster, slinging the finest langosta in town alongside live music, lobster (and non-lobster) art, and costumed lobster mascots. And what better way to cap off Labor Day weekend than a lobster brunch cruise?
Thursday
Sep 8
Soldier Field
Soldier Field hosts a pop-up outdoor movie drive-in thanks to the fine folks at Adult Swim, who blow into town with unaired episodes and pilots, food trucks, trivia, and games. Oh, and did we mention it’s free?
Saturday
Sep 10
Lagunitas Brewery
One of the most anticipated events of the year offers 100+ performers in everything from burlesque and sideshow acts to aerialists and “human-powered carnival rides.” Plus live music, costumes, and, of course, beer. Lots and lots of beer.
Saturday
Sep 10
The Hideout
The Hideout is hosting the Hideout 20-Year Reunion bash block party-style this year, bringing together old friends and an all-day lineup of bands from Hideout vets Jon Langford and Robbie Fulks to local up-and-comers like White Mystery. Come pay your respects.
Saturday
Sep 10
Roscoe Village (Roscoe & Damen)
You know fall is here when you start to hear the sound of slurping at Chicago’s finest celebration of the oyster, with live bands and enough Shock Top beer to arm a small city.
Friday - Sunday
Sep 16-18
Douglas Park
If you’re looking to get riotous (or just calmly ride some carnival rides), it’s all yours for the taking at the unofficial end-of-summer party that is Riot Fest, this year featuring the indie weirdness of The Flaming Lips and Ween mixed with the hardcore punk of The Misfits, Social Distortion, and NOFX. Not to be missed.
Saturday - Monday
Sep 17-19
Lakeview (Southport & Addison)
The mighty taco (and its glorious interpretations from Taco Joint, The Pony, D.S. Tequila Co., etc) deserves a fest in its own right. Throw in lucha libre wrestling and live bands, and you’ve got a serious party on your hands.
Friday - Saturday
Sep 23-24
Various locations
You’re gonna see a lot of people wearing black at Cold Waves, Chicago’s ultracool tribute to industrial music featuring genre icons like Meat Beat Manifesto, The Cocks, and Stabbing Westward at local venues including Metro/Smart Bar and Double Door, sponsored by Kuma’s and Revolution and complete with a Wax Trax pop-up record store.
Friday - Sunday
Sep 23-25
Millennium Park
Celebrity chefs including Rick Bayless and Stephanie Izard join 150+ top local chefs and restos in a culinary orgasm of upscale tastings, chef demonstrations, and seminars, plus the Hamburger Hop burger showdown and Grand Cru wineapalooza.
Saturday
Sep 24
U.S. Cellular Field
Leave it to local hip-hop luminary Chance the Rapper to throw U.S. Cellular Field’s first-ever music festival, complete with a stacked lineup including Skrillex, Tyler, The Creator, Lil Wayne, Alicia Keys, Young Thug, 2 Chainz, and John Legend. This is, quite likely, the best thing to happen at The Cell all year.
Saturday - Sunday
Sep 24-25
Say “aahh” at Common’s Aahh! Fest
Say “aahh” at Common’s Aahh! Fest
One of Chicago’s most thoughtful hip-hop artists brings back this two-day celebration of hip-hop and local culture, as Common is joined by up-and-coming hip-hop/R&B artists Sir the Baptist and Jeremih, plus a local youth talent showcase.
Friday - Saturday
Sep 30-Oct 1
West Town (Chicago & Paulina)
At the West Town Food Truck Social & Art Walk, not only are there 19 food trucks -- there’s also art (visual and fashion) plus tunes spun by local record stores to soundtrack your snack and stroll down Chicago Ave.
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Courtesy of Timberland
October
Freaky Deaky Halloween throwdown
Logan Square Beer Festival | Jeff Lazar Productions

October

Saturday
Oct 1
Find out how much bacon one human can consume in a day
Find out how much bacon one human can consume in a day
Soldier Field
The idea behind the Bacon & Beer Classic is pretty simple: all-you-can-eat bacon-infused dishes from local chefs. 80+ craft beers. Games. A bacon-eating contest. You’ve been warned.
Saturday
Oct 1
Logan Square Auditorium
It’s not like you need an excuse to drink beer in Logan Square. But in case you do, there’s this: Logan Square Beer Fest, uncorking 50+ beers, live bands, and a raffle inside the inescapably high school prom-looking Logan Square Auditorium.
Thursday
Oct 20
Union League Club
Jackets are required and denim is forbidden at the upscale taste of the high life that is the Whisky Extravaganza, complete with unlimited samples of the world’s finest whiskeys, epicurean fare, and a premium imported cigar for later.
Friday - Sunday
Oct 28-30
Toyota Park
Things get freaky, like really freaky, at React Presents’ annual Freaky Deaky Halloween throwdown, this year headlined by Disclosure, Tiësto, and DJ Snake. Yes, there will be clowns. One way or the other.
November
BeerHoptacular | BeerHoptacular

November

Saturday
Nov 5
Cinespace Chicago Film Studios
One of the best events of fall moves into new warehouse digs near Douglas Park this year, complete with 150+ American craft brews ranging from local big boys Revolution and Half Acre to up-and-comers like Arcade and Middle Brow, yours to pair with food trucks and live bands. Like God intended.