You’re having an affair, or you’re secretly dating your best friend’s ex. Or maybe you’re shtupping someone 30 years your senior and you’re not ready for your friends to meet your AARP-member beau. Whatever the reason, you need to keep this thing on the DL. That’s why you’ll be taking advantage of the city’s underground and underused Pedway during this marathon date. Yeah, it’s a little dirty down there, but so is this tryst, no?
Start your rendezvous at noon where many historic events have gone down—a parking garage. Specifically, Millennium Park/Grant Park North parking garage. Think about it: Deep Throat, Michael Jackson’s “Bad” video, that Seinfeld episode where George lost his car…parking garages carry some hefty cultural poignancy. At the northwest corner of Monroe Street and Michigan Avenue, slink down the stairs to the garage, kiss passionately, then look for the yellow-and-blue Pedway signs. Follow the Pedway north for three blocks, then follow signs leading you west to Macy’s till you come across InField’s (111 N State St, lower level, 312-781-3192), a sports bar/restaurant in the bowels of the department store. Didn’t know Macy’s had a basement bar? Exactly. Get a beer or two and brazenly hold hands—no one will spot you here.
You’ve been underground for a while now—you need some air. Follow Pedway signs for Millennium Station, go straight through its food court and hang a left. Go up the escalator, through the Prudential Center lobby (keep your distance from each other here; it’s fairly crowded) and follow signs for the Aon Center. Go up the escalator again and head for the lovely and relatively unpopulated garden, one level below ground near the corner of Randolph Street and Columbus Drive, replete with a geyserlike fountain and waterfalls lining one wall. Grab a seat on a marble bench near the waterfall—the din of gushing water is so loud, you could shout your plans to ravish each other without anyone overhearing.
It’s time for a late lunch and, unfortunately, you’ll have to go above ground for about 10 seconds to get there. Go back through the revolving doors, take a right, then take a left and an immediate right and follow Pedway signs for the Park Millennium condo building. Take the elevator up to the first floor, leave the building, then make a mad dash across South Water Street to the stairway that’ll take you back down to the Pedway’s safe confines. Take a left and hit Khyber Pass (Columbus Plaza, 233 E Wacker Dr, 312-856-1810), an Indian restaurant with a killer $10.95 lunch buffet (try the flaky veggie samosas and the flavorful butter chicken) that includes free nan and tandoori chicken. Better yet: It has no windows.
Is that curry really spicy, or are things getting steamy? Time to get naked. Go back the way you came (including that sprint across South Water), follow signs for the Fairmont Hotel and once inside, head straight for the underground mySpa (200 N Columbus Dr, 312-946-8945, visitmyspa.com). Start with a soak in the two-person tub ($40 for 30 minutes), then get side-by-side massages ($135 each for 60 minutes)—all in a private suite with its own bathroom.
You’re relaxed, titillated and thirsty: Take the elevator up to the Fairmont’s dark, sexy Aria Bar (312-444-9494, ariachicago.com). Lit mainly by candles, this sleek spot offers plenty of tucked-away nooks where you can sip Diablos (tequila, fresh lime juice, simple syrup and soda; $13) and feed each other sushi. But raw fish, citrusy cocktails and mood lighting can only lead to one thing, and the Fairmont is way too swank for your illicit ass. No, you need to grab a cab (better yet, take separate taxis) west to Ohio House Motel (600 N LaSalle St, 312-943-6000, ohiohousemotel.com), where the rooms are so cheap (starting at $99/night) and the building so time-warped, there’s no doubt countless affairs have been carried out right on your bed. On second thought, don’t think about that.