Start your trip on the Magnificent Mile where you can indulge in luxury shopping and dining. The street is lined with designer stores, high-end restaurants, and luxurious hotels. Take in the stunning architecture of the city and explore some of its top attractions like the Chicago Water Tower and the Tribune Tower.
Immerse yourself in the city's art scene by visiting the renowned Art Institute of Chicago. This museum is home to thousands of impressive works including iconic pieces such as Grant Wood's "American Gothic" and Georges Seurat's "A Sunday on La Grande Jatte." Afterwards, head over to the nearby Millennium Park to admire the breathtaking architecture and take photos at The Bean. Relax at the park's other attractions, such as the Lurie Garden and the Jay Pritzker Pavilion.
Take a stroll along the Chicago River Walk and explore the various restaurants, cafes, and bars while enjoying scenic views of the city. After that, head over to Navy Pier - a famous landmark hosting numerous entertainment spots such as the Chicago Shakespeare Theater, sightseeing cruises, and rides at the amusement park. End the day with a fancy dinner at the pier and soak in the stunning views of Lake Michigan.
Chicago has a well connected transportation system consisting of buses, trains, and taxis. The city is also very walkable and many attractions are within a reasonable distance of each other. Taxis and ride-sharing services like Uber and Lyft are also readily available. Average travel costs are around $2.50 for single-ride tickets, $28 for a 1-day CTA pass, and around $40 for a taxi ride to and from the airport.
If you have more time, consider taking a boat tour on the Chicago River or visiting the popular Willis Tower. If you have less time, prioritize the must-see attractions like Millennium Park and the Art Institute of Chicago. Be aware of the weather, especially during winter months as it can be quite cold and windy.
Chicago has two airports: O'Hare International Airport (ORD) and Midway International Airport (MDW). Both are located outside of the city limits with ORD approximately 17 miles northwest and MDW around 13 miles from the city center. Both airports have various options for transportation to downtown Chicago including taxi, rideshare, shuttle services, and public transportation.