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Second City Simulation: Spend a Day in Chicago from Home | Frommer's FeyginFoto / Shutterstock

Second City Simulation: Spend a Day in Chicago from Home

Our one-day itinerary for doing Chicago from afar highlights its best art, architecture, culture, and food. (And some day you can go do these for real.)

There’s at least one benefit to experiencing Chicago virtually instead of IRL. You can travel from spot to spot as fast as your Wi-Fi connection can carry you—no Lake Shore Drive traffic or poky L trains required. 

And think of all the healthy social distancing you’ll be practicing. 

True, seeing Chicago in person is best. But when you can’t do that, here’s a one-day itinerary that will supply a reasonable Second City simulacrum. 

For Breakfast: Cinnamon Rolls and Soul

Start your day with ooey-gooey goodness by attempting the cinnamon roll recipe from Ann Sather, a Swedish-inflected breakfast restaurant dating to the 1940s that has three locations. The generously glazed, pillowy pastries are a North Side favorite.

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While you bake, get into a Chicago frame of mind by listening to the weekly Sunday Service playlist created by D.J. Duane Powell for Stony Island Arts Bank, a South Side favorite. 


Morning Museum Meanderings

Now take yourself on a whirlwind tour of Chicago’s substantial cultural holdings.

Zoom in on fine details of the essential works of the Art Institute's digitized collection. Gather with little ones for story time at the American Writers Museum (streaming Saturdays at 10:30am CDT). Explore African American history via the DuSable Museum’s online exhibit. And participate in kid-friendly interactive games and activities relating to weather, biology, and engineering from the Museum of Science and Industry’s Science at Home series.

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(Grant Wood's American Gothic at the Art Institute of Chicago; photo by Doran Erickson/Unsplash)

Outdoor Break

You’ll have to save your selfie in front of “The Bean” (aka Cloud Gate) at Millennium Park for your next in-person visit. But there are other rewarding outdoor activities you can sample virtually, such as an interactive digital “color safari” through the gardens at the Garfield Park Conservatory and, every day at 11am, a “Bringing the Zoo to You” livestream from the suburban Brookfield Zoo that shows off resident sloths, penguins, big cats, and other critters. 

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For Lunch: A Chicago-Style Hot Dog

Here’s the official preparation, according to Vienna Beef, the city’s hot dog manufacturer of choice: “Grab yourself a bun, preferably one with poppy seeds. Lay a Vienna Beef frank inside. Apply mustard in a zigzag pattern from end to end. Cover it in relish. Sprinkle on some diced onions. Add two tomato wedges on one side. Add a pickle spear to the other side. Add two sport peppers right on top of the dog. Add a dash of celery salt. Ta-da!”


(Image by Brent Hofacker/Shutterstock) 

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To learn more about Chicago’s favorite foods, sign up for one of the virtual food tours offered by Bobby’s Bike Hike on Friday evenings.

Afternoon Architecture

Chicago’s justly lauded architecture encompasses trendsetting skyscrapers downtown as well as trim bungalows and brick “two-flat” buildings in outlying neighborhoods. On weekends, Chicago Detours is offering live virtual excursions ($8) during which guides walk viewers through handsome historic areas and narrate boat rides along the Chicago River, an iconic route for skyline gawking

(Image by Chicago Architecture Foundation)

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Onscreen Sports

For a break from sightseeing, you can catch up with ESPN’s The Last Dance, an obsessive chronicle of Michael Jordan and the 1997–98 Chicago Bulls (streaming on Sling). Or for a classic Chicago-based basketball movie that’s brimming with still-relevant insights on race, class, and growing up, go with Hoop Dreams, Steve James’s wrenching, riveting 1994 documentary (HBO Now, Kanopy, and other streaming services). 

Dinner and a Show

Plan ahead and you can have deep-dish pizza, Italian beef, and other Chicago delicacies delivered at home from Tastes of Chicago, which ships nationally. (We realize that the meals we’ve been suggesting have been on the heavy side but hey, you can chew kale on your virtual tour of Berkeley.)

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While you dine, watch an archived performance on the Joffrey Ballet’s YouTube channel, or join a free Improv House Party from the legendary Second City comedy theater (Tuesday, Thursday, and Saturday nights at 7pm). 


(Image: Wikimedia Commons)

Toast the end of your very Chicago day by cracking open a locally brewed Goose Island beer and laughing at internet clips of strangers trying another Chicago-born alcohol product: Jeppson’s Malört, the worst-tasting stuff in the world. 

And when you can finally travel to Chicago in person, download or pick up a copy of Frommer's Chicago Day by Day to make the most of your time in that toddlin' town.   

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