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Actually Fun Things You Can Do in Chicago This Weekend

Thrillist logo Thrillist 6 days ago Jay Gentile

a large sandwich sitting on top of a table © Cobra Lounge If you’re a fan of over-the-top pop-ups, your Instagram feed is gonna be lit this weekend. Not only are there large-scale “immersive experiences” including a boozy Mad Hatter-themed tea party, a Shining-inspired cocktail bar, and a Halloween-styled Museum of Terror, there’s plenty for you to do this weekend besides cheekily mugging for the camera including a harvest feast with Stephanie Izard and a drive-in drag queen beauty pageant. Here’s everything fun you can do in Chicago this weekend.

Get booze and a tattoo at Cobra’s Lounge’s new Malort pop-up shop

Now open

Cobra Lounge

The new Chicago Craft: A Collective Grip Pop-Up Shop is making its home at Cobra Lounge Thursdays through Saturdays from 1 to 9pm. Stop by for build-your-own-six-packs from local brewers, craft cocktails from local guest bartenders, barrel-aged Malort shots, vintage Riot Fest and local band merch, and an on-site local tattoo artist.

Cost: No cover

Scarf some serious stoner food at Wiz Khalifa’s new Hotbox by Wiz

Now open


Wiz Khalifa’s highly anticipated delivery-only national restaurant chain has finally opened in 15 locations including downtown Chicago, where you can indulge in a 420-friendly menu of stoner food delights including hot Cheetos buffalo mac and cheese and blazed fried chicken sandwiches. Maybe hit up these spots before you order.

Cost: Depends what you order

Join Stephanie Izard and other top Chicago chefs at Harvest Fest: A Socially Distanced Celebration

Now through Sunday

Various locations

Top Chicago chefs including Stephanie Izard, Rick Bayless, Paul Kahan, and numerous others will be on hand at this fall-themed culinary extravaganza featuring a series of socially distanced outdoor events including themed dinners, a pumpkin BBQ, pisco lunches, boozy brunches and more. Get after it, kid.

Cost: $45 and up per event

Get twisted at 'The Shining'-themed Room 237 Pop-Up Experience and Bar

Now through November 15

Morgan Manufacturing

Become a guest at the Overlook Hotel at this massive Shining-themed pop-up experience in a cool 32,000-square-foot historic building featuring multiple rooms with a giant hedge maze, themed cocktails, a hospitality industry party, and more.

Cost: $35 and up

Freak yourself out at the new Museum of Terror

Now through November 22

6th Dimension Space + Gallery

This new two-story exhibit features real-world tales of terror, freaky urban legends, horror memes, photo ops, augmented reality projections, large-scale props, and plenty of disturbing interactive media. Not quite a haunted house, but not that far off either.

Cost: $15-$35

Get sauced at a boozy tea party during the Mad Hatter’s (Gin +) Tea Party

Now through December 31

2239 S. Michigan Avenue

This globally touring immersive experience pops up at an elaborately decorated “hidden garden” on Michigan Avenue where you can sip three original cocktails served in tea cups along with British afternoon tea treats, Mad Hatter-themed attire, and plenty of trippy photo ops.

Cost: $65

Join Pete Buttigieg and Mayor Lightfoot in conversation as part of Chicago Humanities Festival

Friday 2pm


Former South Bend mayor/Democratic presidential candidate Pete Buttigieg joins Mayor Lori Lightfoot in a virtual conversation about trust at this turbulent moment in American history as part of Chicago Humanities Festival.

Cost: Free (registration required)

Attend a drive-in drag queen beauty pageant parody at the Drop Dead Drag Pageant

Friday 6pm & 8:30pm

Lakeshore Drive-In

This Halloween-themed drive-in drag show/beauty pageant parody features performers from RuPaul’s Drag Race, Chicago Local Drag Superstars, and more, in addition to the crowning of the first-ever Drop Dead Pageant King or Queen. Clearly, not your typical Friday night.

Cost: $30-$250

Help support struggling independent music venues by streaming Save our Stages Fest



The National Independent Venues League is hosting this star-studded virtual music festival featuring performances by Foo Fighters, Dave Matthews, The Roots, Major Lazer, Rise Against, and more, with sets filmed at local venues across the country including Metro.

Cost: Free (donations encouraged)

See local neighborhoods in a whole new light during Open House Chicago

Friday through October 25

Various locations

Wholly reimagined for 2020, the annual Open House Chicago architecture fest features a bounty of online and outdoor activities including virtual and in-person neighborhood tours, an artists’ roundtable, virtual discussions, trivia, and more during 10 days across more than 20 neighborhoods.

Cost: Varies by event

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Jay Gentile is an award-winning freelance journalist specializing in travel, food & drink, culture, events and entertainment stories. In addition to Thrillist, you can find his work in The Washington Post, The Guardian, CNN Travel, Chicago Tribune, Lonely Planet, VICE, Outside Magazine and more. Follow @thejaygentile.


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