Chicago

Where to stay:
When you’re looking to catch some shut-eye in Chi-town, give The Drake a rest and book the Peninsula suite at The Peninsula Chicago. You can soak in the hot tub on your private terrace or enjoy the unbeatable view of Lake Michigan. Cool your jets and sweat out stress at the pool and fitness center, located on the top two floors of the 20-story building (108 E. Superior St., 312-337-2888, www.peninsula.com). Three sides are better than four at the Sofitel Chicago Water Tower Hotel. Renowned French architect Jean-Paul Viguier designed the triangular-shaped building, and the same eclectic influence continues throughout the interior. Every detail of the décor from the oversized candles to the specially designed bottles of Evian in each room was carefully selected to give your stay a chic—and unique—feel (20 E. Chestnut St., 312-324-4000, www.accorhotels.com).

Where to eat:
Wake up with brunch at the West Egg Café. You can’t go wrong with the all-day breakfast menu at this always-packed spot (Multiple locations, 66 W. Washington St., 312-236-3322). Since Dallas is to barbecue as Chicago is to deep-dish pizza, stop by Gino’s East pizzeria for lunch. Though the toppings at this low-key local favorite are mostly standard, the taste is anything but (Multiple locations, 633 N. Wells St., 312-943-1124, www.ginoseast.com). If the foodie in you craves more gourmet goods, Charlie Trotter’s is where you’ll want to be. Unfortunately, last minute reservations are hard to come by (they’re taken up to four months in advance), but if you can’t plan ahead, call in the afternoon—when reservations are most often cancelled—and you might be able to score a table for the same night. If you do, your taste buds will be treated to a multi-course medley of flavors that will keep you salivating until your next visit (816 W. Armitage, 773-248-6228, www.charlietrotters.com).

What to do:
Pick your poison. Looking to boost local economy? The Magnificent Mile has hundreds of shops and boutiques where you can do damage to your checking account (N. Michigan Ave., www.themagnificentmile.com). Feeling frugal? Visit Millennium Park, where you can walk on water at the Crown Fountain or admire the city’s reflection in the 33-foot-tall Cloud Gate steel sculpture. After sunset, bring a light jacket so you can catch an outdoor flick or musical performance during the summer months (201 E. Randolph St., 312-742-1168, www.millenniumpark.org). See four states from the Skydeck of the Sears Tower, the tallest building in North America (233 S. Wacker Dr., 312-875-9696, www.the-skydeck.com). If you’re an art aficionado, check out classic works like Grant Wood’s American Gothic and Georges Seurat’s A Sunday on La Grande Jatte at The Art Institute of Chicago Museum (111 S. Michigan Ave., 312-443-3600, www.artic.edu). You can’t visit the Second City without seeing a show by the famous comedy troupe of the same name. With alums like Dan Aykroyd, Bill Murray, and Chris Farley, The Second City Chicago is sure to feature some future SNL cast members and have you laughing all the way back to the hotel (1616 N. Wells St., 312-664-4032, www.secondcity.com). Finally, finish your evening with a nightcap at The Green Mill Jazz Club, a historic hotspot that was one of Al Capone’s speakeasies during the ’20s and is the oldest jazz club in the U.S. (4802 N. Broadway Ave., 773-878-5552, www.greenmilljazz.com).