Begin your Chicago adventure on the Magnificent Mile, a stretch of Michigan Avenue that boasts over 400 stores, luxury boutiques, and high-end restaurants. Walk along this iconic street to see some of Chicago's most famous landmarks, including the Wrigley Building and the Chicago Water Tower.
Spend the morning at Millennium Park, a 24.5-acre public space that features the famous "Cloud Gate" sculpture, also known as "The Bean". After taking pictures in front of the Bean, head over to the Jay Pritzker Pavilion for a live concert or show. In the afternoon, take a stroll or bike ride along Navy Pier, a landmark that offers shops, restaurants, and attractions. End your day with a ride on the Ferris wheel to enjoy breathtaking views of the city.
Explore one of the oldest and largest art museums in the United States, the Art Institute of Chicago. With over 300,000 works of art, including paintings, sculptures, and photographs, there's something for everyone. Make sure to check out iconic pieces like Grant Wood's "American Gothic" and Seurat's "A Sunday on La Grande Jatte."
Start your day by visiting the Skydeck of Willis Tower, the tallest building in the Western Hemisphere. From the 103rd floor, enjoy panoramic views of the city and step onto the glass platform known as "The Ledge." In the afternoon, take a river architecture tour to learn about Chicago's fascinating history through its buildings and bridges. You'll see iconic landmarks like the Tribune Tower, the Wrigley Building, and the Merchandise Mart.
End your trip on a relaxing note by visiting Lincoln Park and Zoo. This 1,200-acre park offers an abundance of walking trails, gardens, and nature exhibits. Don't miss the Lincoln Park Zoo, a free attraction that features animals from all over the world. After exploring the park, head over to the Lincoln Park Conservatory to see exotic plants and flowers.
Chicago is a pedestrian-friendly city, but to get to some of the attractions on this itinerary, you may need to use public transportation or ride-sharing services. The Chicago Transit Authority (CTA) offers trains and buses that can take you anywhere in the city. A single fare is $2.50, or you can purchase a day pass for $10. Uber and Lyft are readily available in Chicago, and their rates are comparable to those in other major cities.
If you have more time, consider visiting the Museum of Science and Industry or the Shedd Aquarium. For foodies, try deep-dish pizza at Giordano's or Lou Malnati's. If you have less time, prioritize the attractions that interest you the most and consider skipping others.
There are two airports in Chicago: O'Hare International Airport (ORD), located 16 miles northwest of downtown, and Midway International Airport (MDW), located 8 miles southwest of downtown. Both airports offer ground transportation options such as taxis, public transportation, and ride-share services. O'Hare is one of the busiest airports in the world and serves as a hub for United Airlines, while Midway is smaller and primarily serves Southwest Airlines.