While some view Chicago as home for debauched politicians, deep-dish and Da Bears, we’ve got a decidedly more sophisticated take on the Windy City. Got 48 hours to explore Chicago? Then follow this cultural-, culinary- and cocktail-filled itinerary for two splendid days in the Midwest capital.
Start off with a jolt of caffeine at Intelligentsia, a local (and beloved) coffee roaster. The Loop location is small, busy and brimming with locals and tourists lined up for the artistically brewed beverages — drink cup-and-saucer style at the counter, or grab a coffee to go before walking over to the city’s foremost museum, The Art Institute of Chicago.
Second in size only to the Metropolitan Museum of Art in New York, this place is packed with vast collections that range from Impressionist paintings to photography. After you’ve seen your fill of Chagall and Monet, peruse the Modern Wing — an architecturally stunning 2009 addition to the museum. Get a table at Terzo Piano for lunch and great views of Millennium Park — your next stop.
Sure, it’s a bit touristy, but walk over to the massive legume-shaped sculpture “Cloud Gate” (Chicagoans colloquially call it “The Bean”) and check out Frank Gehry’s futuristic Pritzker Pavilion bandshell made of large pieces of curved steel. From here, head north on Michigan Avenue for iconic views of the city and some high-end retail therapy (Coach, Neiman Marcus and a brand-new Burberry, the second largest in North America).
Check in to The Peninsula Chicago, a Forbes Travel Guide Five-Star hotel just off the Magnificent Mile. The ultra-luxe hotel has polished and poised service and extravagant rooms with high-tech amenities. Rest up before an elaborate, multi-course meal at Sixteen, the Four-Star fine-dining restaurant at Trump International Hotel & Tower Chicago. While the views of the Wrigley Building clock tower and the Chicago River are worth a visit al
one, the food by executive chef Thomas Lents is, too. Grab a nightcap at The Peninsula’s clubby bar (try to snag a seat by the fireplace). Scotch is a specialty here.
We can’t recommend a stay at The Peninsula Chicago without a visit to its Four-Star, Asian-inspired spa — start Day 2 with a customized treatment and breakfast by the rooftop pool.
It is often said Chicago is a city of neighborhoods, so you’ll certainly want to explore those that lie just outside of the city center. Make your way to the somewhat gritty Fulton Market district to gallery-hop before trekking up to Wicker Park and Bucktown. This area is laden with lunch spots, but go to Big Star for tacos (try the al pastor) and killer margaritas before hitting the hood’s brilliant mix of indie shops and designer boutiques. Cab it over to hipster haven Logan Square for an early dinner at Longman & Eagle, a joint that serves seasonal, elevated gastropub eats like roasted bone marrow and grilled foie gras.
Finally, top off your trip by taking in a show at Steppenwolf, a stalwart of Chicago’s legendary theater scene. Home to Pulitzer Prize-winning writers and Tony Award-winning actors, Steppe
nwolf is a draw even for those who aren’t theater buffs. If comedy is more your style, catch a show at The Second City instead (reserve tickets at least a week ahead of time — they go fast). Known for boosting the early careers of comedians like John Belushi and Tina Fey, this laugh house produces culturally relevant, on-point revues that consistently lure in both visitors and locals looking for a laugh.
Photos Courtesy of The Peninsula Chicago
