Greektown High-Rise Hotel near Chicago’s Loop

Outside the United Center, a 12-foot-tall bronze statue immortalizes an airborne Michael Jordan, who’s depicted at the moment right before he completes one of his signature slam-dunks. The Chicago Bulls have been playing home games at the United Center since the early 1990s, during the latter half of the team’s reign as six-time national champions. Today, fans cheer on the next generation of Bulls players at the gargantuan arena, which also hosts Blackhawks hockey games and a steady stream of music headliners. It stands a little more than a mile west of the Crowne Plaza Chicago Metro hotel on Madison Street. Another Chicago icon is visible from some of the hotel’s guest rooms. The Willis Tower—still known as the Sears Tower to many lifelong Chicagoans—is easy to spot, thanks to its impressive height and trademark fedora. Inside the hotel’s chic executive king rooms, sleek furnishings in neutral hues complement walls adorned with modern art. At the onsite Dine restaurant, chefs whip up American fare with a contemporary twist, such as grilled Atlantic salmon ($26) and wild-boar sausage and penne rigatto ($26). In the dining room, Warhol-esque prints of retro Kitchenaid mixers in neon colors hang near oversize fuchsia booths.

Chicago's Greektown: Mediterranean Dining Minutes from the Loop

The boundaries of Chicago's Greektown neighborhood were established in the 1960s, after the construction of the University of Illinois – Chicago—located a few blocks to the south—displaced the residents of a former Greek enclave known as the Delta. Halsted Street, Greektown’s main drag, is lined with a number of Mediterranean restaurants. Legend has it that the first American versions of gyros and flaming saganaki were created and consumed here in the late '60s. Less than a mile east of Greektown, the tallest building in the western hemisphere climbs to a dizzying height of 1,450 feet. The Willis Tower features an observation deck on the 103rd floor, where 360-degree views stretch 50 miles in each direction on a clear day. On the Sky Deck Ledge, brave visitors and mimes with a sense of irony step out onto glass boxes suspended 1,300 feet above Wacker Drive.