2 Days Chicago Itinerary

Things to do in Chicago, Illinois


Save Time and Money on your trip! We recommend Chicago CityPass which saves upto 51% on museum and other attractions. Go CityPass offers 25+ Chicago attractions and skip the long line to buy tickets.

Day 1

Start your first day in Chicago with a leisurely self-guided tour on the Hop-On Hop-Off Chicago Bus Tour . This bus tour showcases many of Chicago’s best sights: the Willis Tower, Navy Pier and the Museum Campus. Next, breathe in spectacular views of the city from the Skydeck Chicago in the Willis Tower . From 1,353 feet up, you can choose to step out onto The Ledge; glass boxes extending from the Skydeck. If the weather during your stay is cold or rainy, an indoor option is The Art Institute of Chicago . The Art Institute showcases pieces such as George O’Keeffe’s collection, the Chagall stained glass windows, and Grant Wood’s renowned “American Gothic”. An alternative outdoor option is the Chicago Riverwalk and while there, catch The Architecture River Cruise featuring Chicago’s unique architecture. This cruise is 75 minutes and boards by the Navy Pier . Attractions at the Navy Pier include the Navy Pier Centennial Observation Wheel, amusement park rides, theaters and museums. To end the first day, visit Millennium Park . Here you can view art pieces such as the Cloud Gate also known as “the Bean” and check out local events or concerts at the park.

Day 2

Begin your second day with a tour of Chicago’s wide variety of famous museums. For lovers of space and astronomy there is the Adler Planetarium . Also included in the City Pass is VIP Admission to the award winning John G. Shedd Aquarium located in Grant Park. A short walk from the aquarium is the Field museum , a natural history museum with 65,000 exhibits filled with 40 million artifacts. If science interests you, explore the largest science museum in the country, the Museum of Science and industry with capturing exhibits of transportation, weather patterns and so much more. After the museum tour, take a much needed stroll down Magnificent Mile and enjoy window shopping or retail therapy with GUCCI, Chanel and Louis Vuitton. End the day enjoying the sunset 1,OOO feet above Lake Michigan in the 360 Chicago Observation Deck .

Pro Tip: The Chicago CityPass offers affordable tickets and stress- free tours to the city’s best sights. Go City Card - Chicago

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