Curator’s statement
Chicago is a vibrant, world-class city known for its stunning architecture, rich cultural history, and dynamic arts and music scenes. Nestled on the shores of Lake Michigan, it offers a unique blend of natural beauty and urban sophistication. From iconic landmarks like the Willis Tower and Millennium Park to deep-dish pizza and jazz clubs, Chicago delivers an unforgettable experience. Its diverse neighborhoods and warm Midwestern hospitality make it a city that welcomes every kind of traveler.
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Day 1: Intro to Chicago
Start your morning with a stroll through Millennium Park, famous home of “The Bean” and other stunning public art. It’s a great intro to the city’s creative energy, and early mornings mean smaller crowds for photos.
For lunch, head to Revival Food Hall (a 10-minute walk) to sample local favorites in a trendy setting without committing to a full sit-down meal. In the afternoon, take an architecture river cruise—it’s the best way to understand Chicago’s skyline and history from a local guide’s perspective.
End your day at Navy Pier. There are plenty of dinner options here, including Giordano’s for some Chicago-style deep-dish pizza. After dinner, walk through the indoor garden on your way to the Centennial Ferris Wheel. Here you can catch some amazing views of the city skyline at night.
Day 2: World-class museums
Chicago is known for its world class museums. These include, but are not limited to, The Art Institute of Chicago, Adler Planetarium, Field Museum of Natural History, and my favorite the Museum of Science and Industry. If you can only visit one, I highly recommend the Museum of Science and Industry. You can spend most of the day there. Some of the highlight exhibits are the German U-boat captured during WWII, a fractal mirror maze, and the Science Storms exhibit where they make and control two-story-tall tornados.
Day 3: Final day
Spend the first part of your day at Lincoln Park. Take a stroll through the park on your way the the Lincoln Park Zoo. Lincoln Park Zoo is a free, family-friendly zoo, offering close-up encounters with over 200 animal species in a beautifully landscaped, historic setting in the middle of the park. If it’s summer, after the zoo walk over to the North Avenue Beach for some lunch and a swim in Lake Michigan or lounge on the sand.
In the afternoon, head over to Skydeck at Willis Tower (formerly Sear’s Tower) for an amazing view of the city from glass balcony on the 103 floor.
Make your last night in Chicago one to remember with dinner at Sepia (one of Chicago’s Michelin Star restaurants) followed by either a show at one of the city’s Broadway-level theaters, or catch a performance by the Chicago Symphony Orchestra.
Need to know
If you’re planning on a longer trip to Chicago and want to spend some time outside of the downtown area, there are some amazing things to do within a two hour drive from downtown.
Travel Advisor
Robert Fordham-McCracken
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For more inspiration and insider recommendations, visit our Chicago page.