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1. Ronny’s Original Chicago Steak House

Consider this spot, at street level in the Thompson Center, your portal to the Pedway. Don’t be fooled by the “steak house” in the name — this is a cafeteria-style restaurant that also, conveniently, has booze. First stop completed, descend underground via the building’s atrium.
Drink:Your choices are refreshingly simple: beer ($3.50 bottles of Budweiser and Miller) or wine (there’s a $20 bottle of Chardonnay!).

2. Simply Thalia

The Pan-Asian tilt to this spot nestled in the basement of Block 37 means there’s some solid cheap sake to be had. Sit with your back to the entrance, and the lacquered walls and dark wood of the place make it feel less like a sushi restaurant in a sunken mall and more like an intimate hideaway.
Drink:Sake shots ($2)

3. Infield’s

A perfect simulacrum of every Wrigleyville sports bar, except these frosted windows look out onto not Clark Street debauchery but the basement of Macy’s. A little bleak? Maybe, until you discover that happy hour (from 4 to 7 p.m. on weekdays) means $6 old-fashioneds and even cheaper domestic drafts.
Drink:Who can say no to a $5 glass of wine?

4. MBar

Who among us hasn’t dreamed of drinking in a subterranean Metra station? This one boasts a few key perks for commuters: A screen displays info on departures and arrivals, the selection of craft brews is the best in the crawl, and you can buy cans to go. There’s a near-constant turnover of train-riding customers, so you can sit in the same place and strike up five different conversations within 30 minutes.
Drink:Half Acre Daisy Cutter Pale Ale ($6)

5. Red Bar

By day, it’s a Market Thyme dining room frequented by Aon Center workers. But by night (by which we mean 4 to 8 p.m. on Wednesdays, Thursdays, and Fridays), it’s also a bar, complete with groovy brushed-metal decor and high-top tables. Yes, it feels like the clubhouse of a suburban housing development, but hey, the drinks are plenty stiff.
Drink:Daiquiri ($9)

6. Big Bar

After traipsing through the underbellies of the Fairmont and Aqua hotels (there will be a few escalator rides involved, so brace yourself), emerge into the Hyatt Regency to find yourself at a real, honest-to-God plush hotel bar, with leather-backed chairs and massive windows that face the outside world rather than a fluorescent-lit hallway. The main appeal is the riverfront view, but don’t overlook the enormous shrimp cocktail ($22).
Drink:The Bean ($14), a frozen blend of vanilla vodka, Baileys, Kahlúa, and ice cream. You’ve walked a lot today. You’ve earned it.