25 Actually Cool Things to Do in Chicago During Quarantine

Never get bored again.

As you know, the coronavirus pandemic has upended every aspect of our daily lives. But while you can’t go outside and enjoy the city’s fine wealth of bars, restaurants, museums, music venues, and theaters for the time being, you can still recreate the experience at home thanks to the magic of Zoom. Many of Chicago’s businesses have quickly adapted to our new reality with a standout slate of at-home experiences from virtual concerts and remote theatre viewings to virtual river cruises and boozy brunches. And don’t worry, there are still plenty of IRL experiences to help you break your cabin fever, such as outdoor mural tours and nature hikes (just make sure to practice social distancing).

Party hearty with a boozy cocktail kit from a local bar

Even though you can’t be kicking back at your favorite watering hole right now, you can still drink like you are. Thanks to our seemingly endless quarantine, you can now mix any kind of cocktail 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.

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

While we can’t be out at the ballgame munching on hot dogs or cozied up at our favorite pizza slinger, 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 -- the drive-in is still open.

Courtesy of Brass Heart

Recreate the experience of one of the world’s top restaurants at home

Chicago is overflowing with restaurants available for your takeout and delivery orders, numbering more than 1,400 at last count. (Check out our rundown of some of our favorite dishes here.) But if you really want to go all-out and recreate the experience of one of the world’s top restaurants, order from Alinea’s much buzzed-about new to-go menu. You can go casual with some comfort food osso buco and risotto, or go for the gold with their epic six-course tasting menu in honor of the iconic restaurant’s 15-year anniversary.

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 not in an actual office and your suit is now a pair of flannel pajamas? No one.

Catch some virtual improv for some IRL laughs

It’s no secret that we human beings need to laugh now more than ever. Luckily, Chicago’s legendary Second City is here to help. Join them for a variety of virtual shows including the three-times-a-week, freewheeling Improv House Party featuring Second City cast members with rotating special guests. ComedySportz Theater is also taking its infamous improv battles online, with two teams pitted against each other performing for your approval. A “referee” presides over the whole affair with a winner declared at show’s end.

Hit a virtual play

In the Chicago theatre community, Theatre Wit pioneered the concept of remote viewing with its smash hit Teenage Dick, now in its second extension. But it’s far from the only game in town when it comes to the ever-expanding world of virtual theatre. Check out additional offerings from a number of local theatres in the beehive of creative activity that is the Belmont Theater District, including Stupid Shakespeare’s PickleRickicles and Improvised Dungeons and Dragons.

Take a virtual museum and/or zoo tour

As any casual Ferris Bueller fan knows, Chicago has no shortage of world-class museums. And we now have a wealth of remote options for enjoying them. While the penguins at the Shedd Aquarium may have gotten all the attention in the early days of the pandemic, these days the city has rounded out its offering with a comprehensive listing of virtual museum tours including the Art Institute, Museum of Contemporary Art, Field Museum, Museum of Science & Industry, and many more. You can also hang out with animals virtually via a remote zoo tour of the Lincoln Park Zoo. Which you absolutely should do.

Tour the Chicago River and Chicago neighborhoods virtually

Chicago Detours isn’t going to let a global pandemic stop them from doing what they do. Now with a virtual format, the local tour operator is offering a number of options for virtual tours exploring the best of Chicago’s history and local architecture. And for those missing the sheer unadulterated joy of a classic spring/summer cruise down the Chicago River, you can also do that virtually as well. With beer in hand, of course.

Explore Chinatown (and order dim sum online)

There’s nothing against social distancing law that says you can’t still take a stroll around Chinatown, one of Chicago’s most vibrant ethic enclaves. While restaurants are closed, make an order online and do a little urban exploring before you pick up your chow. Local dim sum favorite Phoenix is available for your online ordering, but you might have to recreate their whole push cart experience at home.

Order from a local craft brewery to kickstart your virtual happy hour

There’s nothing worse than showing up to a virtual happy with a can of Miller Lite. Show your civic pride (while drinking, you know, actual good beer) with the help of the Illinois Craft Brewers Guild, who have assembled this handy list of local brewers available for your pickup and delivery pleasure. Yeah, Goose Island is on there, but why not get weird with a new favorite from Marz or Off Color? Now’s the time to experiment.

Go on the ultimate Chicago outdoor mural crawl

One thing Covid can’t stop is the city’s thriving arts scene, which, when museums and galleries are closed, 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.

Catch a movie at a cool old theater… remotely

If you are missing the cool retro feel of Chicago’s legendary Music Box Theatre, you can “bring the art house to your house” with its streaming service Music Box Direct. The collaboration between Music Box Films and Doppelganger Releasing curates a diverse slate of global independent films and TV series, from comedy and documentaries to music and drama. The equally iconic Gene Siskel Film Center is also screening a variety of independent films via their “Film Center From Your Sofa” program.

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. 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?

Rock out at a virtual concert

Pandemic or no pandemic, there’s no stopping Chicago’s live music community. Beloved local dive The Hideout presents Hideout Online via Twitch featuring live streaming music performances, dancing, talk shows, comedy, and yes, bingo. Local blues club Rosa’s is keeping the tunes rocking via Facebook Live, while the crazy cats of FitzGerald’s are driving around the city with a musician in the back of a flatbed truck and livestreaming the whole thing during their “Stay at Home Concert Series.” You can also join a collection of local independent musicians showcasing their talents on Twitch via Experimental Sound Studio’s “Quarantine the Concerts”, or even check out performances live from residential front laws thanks to the virtual edition of the Front Porch Concert Series.

Hit a Chicago virtual festival

While it’s unlikely that any music festivals will be happening in Chicago this summer, you can still get a taste of that glorious Riot Fest vibe thanks to their “Riot Fest At Home” concert series on Instagram Live. You can also pretend you’re in the park taking in an outdoor concert at Pritzker Pavilion thanks to Millennium Park’s Summer Music Series, which showcases past performances on YouTube. Jonesing for a local Chicago street festival? Head over to Star Events’ One City Summer-Long Virtual Festival for contests, videos, deals from local vendors and more as they seek to replicate the Chicago street festival experience virtually.

Recreate your own date night at home

When it comes to dating at home, there are options besides pizza delivery and Netflix. (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, dominate virtual game night with Brooklyn Boulders, or get a little naughty with Michelle L’amour’s sexy Quarantine Cabaret. You can also virtually party with drag queens at the weekly Drag Mati-Net if that’s your thing.

Cruise Chicago’s Emerald Necklace

If your cabin fever is getting the best of you and you simply have to escape the house for the good of you and everyone around you, a scenic drive around the city might be in order. 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 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 less than three 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.

Go out for a walk in nature and clear your head

The restorative power of nature has rarely been as important than after spending a few weeks cooped up indoors. You’d be amazed at how much good a simple stroll around the neighborhood or to your local park can do to your mindset. Turn off the news for an hour two and go for a walk in the fresh air. It’s probably the single best thing you can do for your mental state. Here are a few suggestions, but the park nearest you will do just fine. Oh, and did we mention there is a massive 210-mile nature trail surrounding the entire metro area? 

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.

Hang with the cool kids during a virtual boozy brunch

Chicago’s James Beard Award-winning sommelier Belinda Chang hosts the weekly “Boozy Brunch with Belinda” virtual hangout featuring conversations and demonstrations from some of the leading lights in the local and national culinary scene. There’s also a virtual tip jar to raise funds for laid-off or furloughed restaurant industry workers while you imbibe.

Upgrade your cooking game via a virtual cooking demo

Join Furious Spoon’s Michelin-starred chef Shin Thompson for this hands-on chef’s demonstration on how to cook pork and mushroom ramen like a pro. The livestreamed cooking demo includes a custom two-person ingredient kit for pickup, with add-on optional (but not really optional) DIY cocktail and sake bomb kits.

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 a Thrillist contributor, and he always hits the Times Square Sbarro with Michael Scott whenever he’s in NYC. Follow @thejaygentile.