Go on a Pedway crawl
The Pedway can serve as an underground art gallery if you know where to go. Begin in Block 37 at the Chicago Design Museum, where you can view work by local designers. Make your way east and take in the American Victorian stained-glass windows installed near Macy’s before visiting a free exhibition at the Chicago Cultural Center. Finally, head south through the parking garages, exit on Monroe Street and you’ll see the iconic lions guarding the Art Institute of Chicago.
Start this one at Block 37, where Gayle’s Best Ever Grilled Cheese, a farmers’ market staple turned regular fixture as a Loop lunch spot, lives up to its name. Dig into the Classic grilled cheese, made with Prairie Pure butterkäse, before heading east to pop into Infield’s, the Chicago sports bar in the belly of Macy’s, for a quick beer. Cap it off at Mariano’s on the far east end of the Pedway (accessible near the Aon Center), to stock up on brews and cheese before heading to the CTA to make your way home.
Okay, so technically this tour means you will eventually spend some time outside, but at least you can stay warm and toasty as long as possible. Head to Millennium Park and exit on Michigan Avenue for ice-skating under the Bean. Alternately, bring your own skates and jump the line at the Skating Ribbon at Maggie Daley Park for a few laps around the curvy rink. Once you’ve had enough of the cold, navigate your way south to the Game Room at the Chicago Athletic Association for a cocktail and a game of bocce.
Maintain your out-every-night summer lifestyle even in the blistering cold with access to great cultural institutions just off of the Pedway. The Harris Theater is accessible near the far east branch of the Pedway, while the Chicago Theatre and the Goodman Theatre are both a stone’s throw from multiple Pedway entrances off State and Dearborn Streets. All three offer a ton of great programming this winter. Before your show, grab dinner at the Dearborn (45 N Dearborn St), accessible through Block 37.
Take a long lunch break and start your four-course meal with french fries from hometown fast-food chain M Burger in the Thompson Center Atrium. Then take the Pedway east to Block 37 and grab a taco (or two) from Latinicity. Next, it’s on to Macy’s Seven on State food court for a bowl of shoyu ramen from Noodles by Takashi Yagihashi. If you have room for dessert—and have a taste for icy sweets in the cold weather—take the Pedway south (exit near Chase Tower) and grab Black Dog Gelato from Revival Food Hall.
Duck out of work for a happy-hour crawl that starts at Block 37’s Simply Thalia, where you can nosh on hand rolls over a cocktail or beer. Head east through Block 37 past the Red Line and into Macy’s for a glass of red at the Wine Bar at the Walnut Room, which is particularly stunning (and crazy busy) in the pre-holiday weeks, to gaze at the intricately decorated Christmas tree. If you started early and the Pedway is still open, trek back underground and northeast toward Millennium Station to finish at M Bar.