Actually Cool Things You Can (Still) Do in Chicago Right Now

Fun still exists. We promise.

As the pandemic wears on and restrictions continue to tighten across the city and the country, it can be hard to stay upbeat. That’s why you need fun now more than ever. And while most of Chicago’s iconic winter events from the Chicago Auto Show to the Cubs Convention have been either cancelled or postponed, that doesn’t mean there’s no fun to be had during this season of darkness. You just have to look a little harder. Here’s everything fun you can (still) do in Chicago this winter. Be safe and wear a mask, and be sure to monitor local sites for the latest closures and safety information.

Do some ice curling at a local beer and sausage bar

Not only is Kaiser Tiger one of Chicago’s best spots for beer and sausage. It also hosts ice curling on the outdoor patio every winter, even in 2020. Cost is $50 per lane for 30 minutes for up to four players, and reservations are required. 

Grab some winter reading material from a local bookstore

There’s nothing like settling in with a good book during a winter snowstorm. Support local independent bookstores by masking up and paying a visit to a cool local spot like Quimbys or Myopic Books, both of which offer curbside pickup. No, it’s not as easy as Amazon. Which is kind of the point.


Cebu Chicago chicken
Participating in Chicago Restaurant Week | Courtesy of Cebu Chicago

Gorge yourself during Chicago Restaurant Week

We’re not sure what exactly this iconic annual restaurant showcase will look like in 2021, but we’re assuming there will be some sort of a virtual/takeout component. All we know for sure is that, according to the city, Chicago Restaurant Week 2021 “will look a little different this year.” So check back for updates.

Unleash your inner Bill Murray at Woodstock’s Groundhog Days

A road trip to Woodstock is always in order for the town’s annual Groundhog Days festival, which tours several Woodstock filming sites from the 1993 Bill Murray classic Groundhog day. The festival is still on for 2021 in scaled back form from January 30 - February 2, with a handful of events on the calendar including a walking tour of filming sites, trivia, and, of course, the groundhog prognostication.

Discover a new meaning of “chill” at the Chicago Polar Plunge

One way or another, the annual plunge into the icy waters of Lake Michigan in your favorite Speedo or costume at this annual “winter swimming” event raising money for Special Olympics of Illinois is happening this year. It just might not be the same event you’re used to. Organizers state that it is “too early to determine the format” for the 2021 Chicago Polar Plunge—scheduled for March 7—but they say it’s currently game-on.


Get your fill of holiday classics at a local drive-in movie theater

One positive byproduct of this endless pandemic is the preponderance of drive-in movie locations across the city, several of which are open for the holidays for your drive-in holiday movie pleasure. Hit up Chi-Town Movies, the Drive-In at Lincoln Yards, and SeatGeek Stadium for a range of seasonal classics from Elf to Die Hard. There are also two new pop-up holiday drive-in movie experiences from the folks at Replay including the Miracle on West Madison downtown and the Holly Jolly Drive-In in Lincoln Park. Movies are screening through December 26, and may be extended after.

Get in the spirit by checking out a holiday light display

From Lincoln Park’s iconic ZooLights and the Brookfield Zoo’s Holiday Magic to the Morton Arboretum’s Illumination and Chicago Botanic Garden’s Lightscape, there’s no shortage of brilliant holiday light displays across the city and suburbs. You can also check out Let It Shine in Northbrook or the Aurora Festival of Lights. Closer to home, Art on theMART is the world’s largest permanent digital art projection—screening on the side of the Merchandise Mart nightly through the end of the year.

Party in your car at House Party at the Drive-In New Year’s Eve Bash

What better way to close out this weird year than a New Year’s Eve party from the comfort of your car? Stop by SeatGeek Stadium’s House Party at the Drive-In New Year’s Eve Bash for a full lineup of live house music performances with food/drink and a fireworks show to bid farewell to this shitshow of a year. Masks and social distancing required, obviously.

Sip seasonal cocktails in your very own gingerbread house at Whiskey Business

Wicker Park rooftop bar Whiskey Business is getting into the holiday spirit by converting its rooftop cabanas into heated gingerbread houses available for private rental. The holiday decorated gingerbread houses will include candy canes and fake fireplaces, with seasonal cocktails available to order and an online contest to win a gift card. Reserve yours here.

Get lost in some local nature

The Chicago Lakefront Trail remains open, but it’s not the only place to get some fresh air in the city. Did you know the entire Chicago metro area is surrounded by a 210-mile nature trail complete with Cook County Forest Preserve campsites and lakes? How about a 2.7-mile urban hiking trail along a former railway corridor? How about one of America’s newest national parks just across the Indiana border? If all else fails, your local park will do just fine.

Support Chicago’s Black Community

Whatever else you do this winter, be sure to do your part and make the community we live in a better place for all its residents. Aid in the fight for racial justice and social equity taking place across the city, while also supporting Chicago’s Black community from nonprofits and community organizations to restaurants and bookstores. Here's our guide to doing just that.

Take a quick road trip to discover some Illinois hidden gems

With air travel down and car travel up, it’s no secret that the Great American road trip has made a spectacular return in 2020. Luckily, you don’t have to travel too far to check out some amazing spots right here in Illinois -- from the quaint small town vibes of Galena to the sprawling Shawnee National Forest near Carbondale. Check out some more options here and, if you’re looking to cross state lines, we’ve got you covered here.

Go see some live music (virtually)

While we aren’t yet ready for packed sweaty shows in crowded clubs, there are plenty of excellent virtual options from The Hideout, Empty Bottle, Lincoln Hall/Schubas, Experimental Sound Studio, and more. The City of Chicago is also hosting its own streaming channel as well in honor of “The Year of Chicago Music.” And whatever else you do, be sure to help support the National Independent Venue Association if you don’t want 90% of the country’s independent music venues to close for good.

Try to laugh during a pandemic

If Netflix reruns of The Office aren’t quite as funny as you remember them, you might need to turn to the experts for your comedy fix. Comedy clubs across the city are doing their best to keep you laughing through America’s ongoing nightmare, so be sure to tune into the virtual editions of Second City, ComedySportz Theater, Cornservatory, Annoyance Theater, and others.

Lace up the skates at Maggie Daley Park

While there will be no ice skating at Millennium Park this year, you can still lace up the skates at the Maggie Daley Park Ice Skating Ribbon. Reservations are required, and can be made here. Over in the burbs, you can also get your skate on at Parkway Bank Park in Rosemont.

Book your own private escape room

We’re not sure why anyone would want to voluntarily trap themselves inside an escape room after a year of living a real-life escape room experience. But hey, to each their own. We don’t judge. Popular local escape room Fox in a Box may be currently closed, but they are offering virtual escape room experiences in what they are calling the Live Remote Bunker room. How very 2020.

Party hearty with a boozy cocktail kit from a local bar

It’s no secret that it’s been a rough year for Chicago bars. And while they are currently being forced to close at 10 pm due to covid, you can still mix a cocktail at any hour of the night from the comfort of your home—from upscale offerings by folks like The Aviary and Violet Hour to more down-to-Earth booze creations such as Big Star margaritas and Twisted Spoke Bloody Marys. You can also go tiki with tropical creations from 3 Dots and a Dash, which you obviously should do.

Order in Chicago’s holy trinity of hot dogs, pizza, and Italian beef

While we can’t be out at the stadium munching on hot dogs and pizza, we can still recreate the holy trinity of signature Chicago foods thanks to the miracle of takeout. Order delivery from old-school Al’s Beef for your Italian beef fix, dial up Pequod’s for some amazing caramelized-crusted deep dish delights, or make your way over to Superdawg for the classic Chicago-style hot dog experience—and yes, the drive-in is still open.

Prepare for your at-home power meeting Zoom session with a Manny’s Deli order

It's been a last meal request. It's been a hangover cure. President Obama dined there. As did President Clinton. As did just about every politician who ever set foot in Chicago. And so should you. Power lunch on a Reuben or beef pastrami with a takeout order from this legendary cafeteria-style diner where business (and the occasional shady deal, of course) gets done in Chicago. Who cares if you’re still not in an actual office and your suit is now a pair of flannel pajamas? No one. Order pickup or delivery here.

Go on the ultimate Chicago outdoor mural crawl

One thing Covid can’t stop is the city’s thriving street art scene, which can best be enjoyed IRL via an urban mural crawl. Start your excursion in Pilsen, where dozens of vibrant murals turn the neighborhood’s streets and alleys into an outdoor feast for the senses. Check out standout options like the Hector Duarte Studio at 1900 W. Cullerton before making your way to Logan Square to marvel at the famous Robin Williams mural outside Concord Music Hall and the nearby “Greetings From Chicago” mural at 2226 N. Milwaukee. Finish the mural crawl with a trip to Rogers Park, where you can see a mile-long stretch of wall art along the Red Line path as well as the brightly colored seawall of murals off the lake at Tobey Prinz Beach Park.

Check out the public art downtown (while social distancing, of course)

Looking to get out of the house and stretch your legs a bit? Yes, you can go see The Bean, but don’t stop there. Swing by the “Chicago Picasso,” or the Calder “Flamingo.” Head down to the southern end of Grant Park to walk among the giant, headless sculptures that make up “Agora.” Take a selfie with the Art Institute lions. And be sure to check out the new “People in Your Neighborhood” installation along the Chicago Riverwalk between Lake and Franklin. The concentration of world-class public art in downtown Chicago is astounding and not to be missed. And, most crucially of all, still open during a pandemic. Just keep your six feet, okay?

Recreate your own date night at home

When it comes to dating at home, there are options besides pizza delivery and Hulu. (But if you are getting takeout, hit up the fondue from Chicago’s romance mainstay Geja’s Café.) Otherwise, you can nerd out with some digital cosplay with GeekHaus, get creative at a virtual paint and sip party with VIP Paints, or get a little naughty with Michelle L’amour’s perennially sexy Quarantine Cabaret.

Cruise Chicago’s Emerald Necklace

A scenic drive around the city is never a bad idea, especially before winter kicks in.Yes, you could certainly cruise Lake Shore Drive. And by all means, you should. But for a lesser-known option that allows you to see the actual beating heart of the city instead of just highway, seek out Chicago’s Emerald Necklace, a 26-mile network of interior city streets and wide boulevards. Linking together some of the city's most grandiose parks like Humboldt, Garfield, Washington, and Jackson parks, this is the way Chicago was meant to be seen -- with the added bonus of being excellent quarantine therapy.

Make a mental health pilgrimage to the Shit Fountain

If you’re in the Ukrainian Village area and looking to do the whole public art crawl thing, you may not have as dense of a concentration of murals as Pilsen or as many fine art sculptures as downtown. But you have one thing those other places can’t touch: the one and only Shit Fountain. The human feces-shaped sculpture is located on a residential front lawn just off Augusta and Wolcott, created by a Chicagoan fed up with dog poop. Cheers.

Smoke some of Illinois’ “essential” legal green

Who knew that just a few months after Illinois became the 11th state to legalize recreational marijuana that a full-blown public health emergency would bring our society to its knees? Can you imagine dealing with the current situation without a little green? We don’t even want to imagine it -- and you don’t have to either. Deemed essential businesses, Illinois marijuana dispensaries are still open for business, with certain restrictions depending on the business. Check out our full dispensary rundown for details.

Listen to a local podcast

Finally, you have plenty of time to catch up on that podcast you’ve always been meaning to listen to. Luckily, Chicago is rife with an array of interesting options. Get your politics fix with David Alexrod’s The Axe Files, nerd out on music with Greg Kot & Jim DeRogatis’ Sound Opinions, learn about unique aspects of local city life with WBEZ’s Curious City, drink virtual beer while exploring the brewing industry with Good Beer Hunting, or give Hollywood a lesson or two via Chicago-based Please Make This. And that’s just scratching the surface.

Take a virtual tour of Chicago filming locations

Chicago has long been a popular TV and movie filming location, and the City of Chicago has assembled some of the finest spots to appear on both the big and small screen that you can visit during the age of coronavirus. On the tour of movie filming sites, hit up outdoor screening locales from Blues Brothers, High Fidelity, The Untouchables, and more. On the tour of TV filing sites, check out Google Street View images of sites such as the Gallagher House from Shameless, Molly’s Pub from Chicago Fire, District 21 Police Station from Chicago PD, and more.

Discover a new cool neighborhood

While you’re cooped up during Covid, it can be tempting to never leave your six-block radius. But if you look at things another way, there’s never been a better time to discover a new favorite 'hood. As any Chicagoan knows, the real heart of the city lies within Chicago’s spectacularly diverse 77 neighborhoods. From the laid-back residential enclave of Norwood Park to the cool historic sights of Bronzeville, there’s always a new neighborhood to explore in a city that’s meant to be explored on foot. Yes, even during a pandemic.

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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