Millennium Park, located in the Loop community area of Chicago, is an expansive public park that houses some of the city's most famous landmarks, sculptures, and gardens, including the famous Cloud Gate. After checking out these iconic spots, spend the afternoon strolling along The Magnificent Mile, Chicago's premier commercial district that is home to numerous luxury retailers and dining options.
Explore the Museum Campus, dedicated to showcasing some of Chicago's finest institutions, such as the Field Museum, the Adler Planetarium, and the Shedd Aquarium. Afterward, head to Navy Pier, a popular entertainment destination that boasts various carnival rides, restaurants, and an IMAX theater.
No trip to the Windy City is complete without visiting Wrigley Field, home of the Chicago Cubs. Even if it's not baseball season, stopping by the field is a must for sports fans. In the afternoon, check out the Lincoln Park Zoo, a free zoo that houses over 1,000 animals. Take a stroll through the park and enjoy the lush greenery that this urban oasis has to offer.
The Art Institute of Chicago is home to one of the largest collections of impressionist and post-impressionist paintings in the world. Afterward, spend the afternoon shopping along The Magnificent Mile or check out the city's best restaurants in the River North neighborhood.
Return to Millennium Park and visit the famous Jay Pritzker Pavilion for free concerts, shows, and events. In the evening, head to Second City Comedy Club, a famous comedy club that has produced some of the most famous comedians in the industry.
Take a tour of Willis Tower, the tallest building in the Western Hemisphere, and get a stunning view of the city from the top. Afterward, visit the Chicago Riverwalk and hop on a river cruise to learn more about the city's architecture and history.
Start the day by visiting Garfield Park Conservatory, a botanical garden that has a large collection of exotic plants and flowers. In the afternoon, head to Buckingham Fountain, one of Chicago's most iconic landmarks and a popular spot to take photos.
For transportation within the city, it is recommended to use public transportation, such as the "L" train or buses. Taxis and ride-sharing services like Uber and Lyft are also available, but these can be more expensive. A 7-day unlimited Ventra pass is available for $33, which is a great deal if you plan to use the public transportation system a lot.
To get to and from O'Hare International Airport, taxis and ride-sharing services are available, but the most economical option is to use the CTA Blue Line, which connects directly to the airport and various parts of the city. The fare is $5-$6 per person per trip, and the journey takes around 30 minutes.
If you have more time, consider taking a day trip to the nearby city of Evanston, just north of Chicago. This charming college town has a picturesque downtown area, a vibrant main street, and several parks and gardens.
If you have less time, consider skipping some of the museums or attractions and focusing on exploring the neighborhoods and trying the local cuisine. Chicago is known for its deep-dish pizza, hot dogs, Italian beef, and various other foods that are not to be missed.
Chicago has two main airports: O'Hare International Airport (ORD) and Midway International Airport (MDW). O'Hare is the larger airport and is located approximately 17 miles northwest of the city center. Midway is smaller and located approximately 10 miles southwest of the city center.