Chicago is the third largest city in the U.S., after New York and Los Angeles, which makes it tough to pack into just one weekend, but not impossible with insider tips to the Windy City.
On Friday night, kick off the weekend with a toast on the 95th floor of the John Hancock Building and admire the glitzy Chi-town skyline from on high. When it was built in 1968, the 100-story skyscraper was the tallest building in the city (and the tallest in the world outside of New York City). While only the fourth tallest in Chicago today, the Hancock is still the hottest—and highest—place for a cocktail.
Plan to spend Saturday indulging in Chicago’s top three must-do’s: museums, deep-dish pizza and the 26-mile lakeshore. Start at the Art Institute of Chicago, located in the city’s Grant Park. This world-famous museum is the second largest in the country, behind New York’s Metropolitan Museum of Art, with more than 260,000 works of art displayed in 1 million square feet. Visitors have been known to spend days taking in the collections and exhibits at the Institute—there are 30 Monet paintings alone—but if you want to fit in other Chicago hotspots, it’s important to keep it to just one morning.
For lunch, head to Lou Malnati’s Pizzeria, located 1.4 miles from the Art Institute on North Wells and Hubbard Streets. Opened by the son of Rudy Malnati, the man largely responsible for creating the famous Chicago-style deep-dish pizza, Lou Malnati’s has grown to become the quintessential Chicago pizza chain. While there are thin crust pizzas available at Lou Malnati’s, it’s practically a crime not to choose a big, juicy deep-dish during a first visit.
Saturday Afternoon and Evening
After lunch, drive four miles southwest to the city’s museum campus on the shore of Lake Michigan, to the Shedd Aquarium. One of Chicago’s most popular attractions since 1930, the aquarium was, at one point, the largest aquarium on the planet. Today it houses more than 650 species of fish, reptiles, amphibians, invertebrates, birds and mammals from across the globe. The Oceanarium exhibit is a local favorite, featuring the curious and charismatic beluga whales, as well as dolphins, sea otters and sea lions.
The museum campus sits on Chicago’s Lakefront Trail, an 18-mile walking, running and biking path along Lake Michigan. Before dinner, take a stroll between the deep blue waters of the lake and the city’s silver skyscrapers. The trail passes by harbors, wildlife sanctuaries, four parks and most of Chicago’s beaches. Few, if any U.S. cities have a waterfront trail of this magnitude.
The best Sunday mornings in Chicago begin with brunch and a Bloody Mary. Two classic choices are Walker Bros. Pancake House and Ann Sather. Both have become institutions in the brunch-centric Chi-town. Family-owned Walker Bros. has been flipping pancakes for more than 50 years, with six locations in the city. Ann Sather was founded by a Swede who has since passed, with four restaurants now owned by a local Irish lad with French culinary training who has stayed true to Ann’s Scandinavian roots. For a lesser-known, more off-the-beaten path experience, locals prefer the Birchwood Kitchen, a contemporary eatery focused on locally grown organic food. The Birchwood is BYO, so come equipped with vodka and Bloody Mary mix.
After brunch, get out on the Chicago River and take in some of the city’s world-renowned architecture with a boat tour conducted by the Chicago Architecture Foundation. The 90-minute Architecture River Cruise takes guests aboard Chicago’s First Lady for an interpretation of 50 famous landmark buildings along the river including Willis Tower, Navy Pier, Wrigley Building, Tribune Tower, Merchandise Mart, Lyric Opera, 333 W. Wacker and Marina City. Tours depart every hour on weekends, and cost $38 at the dock, or $35 in advance.
Cap off 48 Hours in Chicago with an unforgettable dining experience. Rick Bayless, the Top Chef Masters Winner in 2009, owns a block of restaurants downtown, including three Mexican style establishments in the same building on North Clark Street. Depending on preference and price point, diners can choose from the casual yet gourmet Frontera Grill, the sexier, spendier Topolobampo or the hip street food of XOCO.
Whatever you fit into your 48 hours, remember: The Windy City got its name for its competitiveness with neighboring Cincinnati, so a keen sense of pride percolates into all aspects of the city. You will not be disappointed.