Photo by Clayton Hauc, courtesy of Cherry Circle Room


Where to Eat and Drink When You Play Hooky in Chicago


Chicago is the home of arguably the most famous fake sick day ever taken. In 1986, Ferris Bueller taught us all that life moves pretty fast, and if you don’t stop to look around every once in a while, you might miss it.  

Take a page out of Bueller’s book and play hooky, with all the activities — and the eats and drinks that go along with them — you need for your own iconic day. Worried about running into your coworkers? The key is to get outside of your normal routines. Instead of your usual lunch spot or happy hour hang, use our guide to plan the best — and most delicious — day off ever. 

Photo courtesy of Cubaneo
Photo courtesy of Cubaneo

Ride along the lakefront to a killer breakfast 

Chicago is a city with many modes of transportation, and when you live here it can be easy to forget all of our options. On a hooky day, skip your usual commute and hop on a Divvy Bike or scooter to take a ride along the lakefront. 

Depending on whether you take your morning ride north or south, you may end up in a neighborhood you don’t normally dine in. If the northside is where your scooter docks, hit up Cubaneo in Lakeview for its excellent Cuban breakfast. Enjoy a café con leche with guava pancakes or take the brunch route and dive into a namesake Cubano sandwich filled with 24-hour slow-roasted pork. 

If  your morning ride takes you a different direction, The Cherry Circle Room  at the Chicago Athletic Association is a perfect hideaway. Tucked into the Chicago Athletic Association, the Cherry Circle Room has a James Beard award-winning design and a cozy old-school vibe, with breakfast daily and brunch on weekends, where they turn out fluffy milk bread French toast, Japanese-style breakfast sets, and rich scrambled eggs with brie. 

Wentworth Ave., in the heart of Chinatown. Photo by Kevin Pang
Wentworth Ave., in the heart of Chinatown. Photo by Kevin Pang

Kayak down to Chinatown for dim sum and cocktails 

Taking in the sights might seem like a touristy activity, but appreciating the architectural wonders that Chicago has to offer is a perfect day-off activity. Head to Ping Tom Park at the South Branch of the Chicago River, where you can rent a kayak and see a view of the city that tourists and residents alike don’t often experience. 

After your kayak adventure, you’ll be in beautiful Chinatown. The neighborhood offers historic architecture, shops with art, ceramics, beauty products, and of course, plenty of food. Dolo Restaurant and Bar, a small dim sum spot, is the only restaurant in Chinatown with a full bar. Why not have a cocktail? You’re out of the office, after all. Dolo’s signature dish puts all sad desk lunches to shame: meet the DOLO style seafood combo, which involves five pounds of fresh crab legs, crawfish, clams, shrimp, sausage, corn, and potatoes, served in homemade Cajun sauce. 

Excellent for hooky-playing. Photo courtesy of Cindy’s Rooftop
Excellent for hooky-playing. Photo courtesy of Cindy’s Rooftop

Activity: See a Broadway show and the city’s best rooftop bar  

When do you ever have time to watch a Broadway musical in the middle of the day? On your hooky day, of course. The James M. Nederlander Theatre has been open since 1926 and is ornamented with beautiful Asian art. Whether it’s “Hamilton” or  “Spider-Man,” use today to catch a matinee at one of the many theaters that are part of Broadway in Chicago.

After the show, you can swing back over to the Chicago Athletic Association and take in the incredible views from Cindy’s Rooftop. With a new chef at the helm, this perpetual hot spot has a new menu and an attitude to boot. There’s a special midday menu with snacks like toasted nori popcorn and a shrimp and lobster roll, along with more cocktails to ease you into the evening.

This could be you after a Sox game. Photo courtesy of Niu B
This could be you after a Sox game. Photo courtesy of Niu B

Work up an appetite at a baseball game 

Whether you’re from Chicago or not, who you choose to root for when it comes to the Cubs versus White Sox says a lot about you. But we’re not here to judge your baseball preferences — we’re simply here to tell you that there’s great eats to be found around both stadiums. 

After the game, if you find yourself walking out of the friendly confines, head over to Savannah Luncheonette in  Wicker Park/Bucktown for comfort food like Steak N’ Fries, burgers, and a hot chicken sandwich. Or, if your Southside pride has you leaving Guaranteed Rate Field, head to the South Loop and take a seat at Niu B Sushi & Noodle Bar, which conveniently has plenty of room to meet up with friends after they get off from work. The vast menu spans everything from sushi to ramen — but do try the octopus-stuffed takoyaki, and the crunchy maki with shrimp tempura and shredded crab. 

Photo courtesy of Chef’s Special
Photo courtesy of Chef’s Special

Explore classic works of art … and classic Midwestern cuisine 

This wouldn’t be a Chicago hooky guide if we didn’t include a recommendation to peruse the world-class displays at the Art Institute. You could recreate the iconic scenes from Ferris Bueller’s Day off or learn the history behind classic pieces. Either way, a couple of hours immersing yourself in sculptures and abstract installations isn’t the worst way to spend an afternoon. 

Once you’ve had your fill of modern masterpieces, take a walk near the Chicago River and step into Hoyts Tavern. This classic Midwestern spot offers old-fashioned American fare with a twist — think duck fat-fried Marcona almonds, short ribs in a Dr. Pepper glaze, and a very tempting waffle iron soufflé. 

Laugh until your stomach hurts … then eat some more 

Playing hooky all day can take a lot out of you, so you may want to kick back somewhere, relax, and have a laugh before getting back into the grind. Your destination? The Lincoln Lodge in Bucktown, which offers weekly comedy shows and variety acts, ranging from sketch to improv and even musical comedy. 

To ease those belly laughs and to cap off your fun-filled day, head nearby to Chef’s Special Cocktail Bar. The team from Giant is behind this upmarket spin on well-recognized Chinese American classics like Mongolian beef and potstickers, served family style. Along with the food, Chef’s Special has a cocktail menu bursting with bright, tropical flavors — don’t leave without trying the signature ChiChi Colada, with coconut and orange blossom, and toasting to a day away from the office. 

Angela L. Pagán is a Chicago-native journalist with a passion for both food and writing. Read her reports on the fast food industry, food trends, and more here, and see more of her writing here. While you’re at it, give Resy a follow, too.