Whether spending a weekend in the Windy City or planning a midweek adventure, you have plenty of time to discover Chicago’s highlights in two days. From world-class museums and world-ranking skyscrapers to the city’s delectable dining scene, here’s how to make the most of your 3-day stay.
Day 1: The Loop and Beyond
Morning: Set right along the waterfront, Chicago’s Museum Campus (home to the Field Museum of Natural History, the Adler Planetarium, the Shedd Aquarium, and more) is the perfect place to immerse yourself in the Windy City’s cultural side. The Art Institute of Chicago, located nearby, and immortalized in Ferris Bueller’s Day Off, is another essential stop.
Afternoon: The Loop, Chicago’s downtown business district, is home to a heavy concentration of landmarks. The neighborhood is ideal terrain for walking tours—explore on foot and stumble across highlights ranging from Millennium Park and the Willis Tower (formerly the Sears Tower) to public sculptures by Pablo Picasso and Alexander Calder.
Night: Head up to the top of the Willis Tower, where you can enjoy a multicourse meal while taking in views of Chicago lit up after dark. Alternatively, a dinner cruise along Lake Michigan combines gourmet dishes with splendid skyline views.
Day 2: Sand and Surf, Snacks and Sightseeing
Morning: On Chicago’s 26-mile (42-kilometer) shoreline, admire what might look to be the ocean—a stretch of Lake Michigan often called the “Third Coast.” When the sun’s out, follow Chicagoans to the lake’s sandy beaches, from North Avenue Beach to Oak Street Beach. Alternatively, enjoy waterside attractions of a different kind at Navy Pier.
Afternoon: Complete this day with a food tour of Chicago’s vibrant culinary culture. Seek out hot dogs and Italian beef sandwiches, and save extra room for deep-dish pizza. A number of renowned, decades-old pizza joints can be found right in the Loop, from Lou Malnati’s and Giordano’s to Gino’s East.
Night: When the sun is setting, embark on a helicopter tour and get rewarded with a unique, aerial perspective of the city. Spot Chicago’s most distinctive skyscrapers, discover its different neighborhoods from the air, and see the lights come on as evening descends.