Four-Day Adventure in Chicago Itinerary

  • Day 1: Millennium Park and Navy Pier
    10 minutes (2.2 miles) from Downtown Chicago

    Start your adventure by visiting the Millennium Park, home to the famous Cloud Gate sculpture, also known as “The Bean.” Enjoy the beautiful skyline and the unique architecture of the park. After that, head to the Navy Pier, a popular tourist attraction with numerous restaurants, shops, and entertainment options. Don't forget to take a ride on the giant Ferris wheel while enjoying the beautiful views of Lake Michigan.

  • Day 2: Skydeck Chicago and Willis Tower
    13 minutes (2.5 miles) from Navy Pier

    Start your day with breathtaking views of Chicago from the Skydeck Chicago, located on the 103rd floor of the Willis Tower. Walk out onto the glass ledge and look straight down to the ground. Then visit the Willis Tower, known for its iconic architecture and stunning views. Get a glimpse of the city’s skyline from the observation deck on the 94th floor.

  • Day 3: Chicago Riverwalk and the Art Institute of Chicago
    15 minutes (3.1 miles) from Willis Tower

    Go on a relaxing stroll along the Chicago Riverwalk, a scenic promenade along the Chicago River with plenty of bars, restaurants, and stunning views. After that, visit the Art Institute of Chicago, one of the oldest and largest art museums in the United States. The museum houses an impressive collection of modern and contemporary art, classical sculptures, and more than 30 impressionist and post-impressionist paintings.

  • Day 4: Lincoln Park and North Avenue Beach
    20 minutes (4.2 miles) from the Art Institute of Chicago

    Head to Lincoln Park, Chicago's largest park, home to a free zoo, two conservatories, and various galleries. Take a stroll or rent a bike along the lakefront path and enjoy the stunning views of Lake Michigan. Wrap up your adventure by visiting North Avenue Beach, a popular public beach with clean sand, clear water, and a beautiful view of the city skyline.

Time and Costs Estimates

  • Millennium Park (1-2 hours, free)
  • Navy Pier (2-3 hours, $20-40)
  • Skydeck Chicago (1-2 hours, $25-50)
  • Willis Tower (1-2 hours, $25-50)
  • Chicago Riverwalk (1-2 hours, free)
  • Art Institute of Chicago (2-3 hours, $25-50)
  • Lincoln Park (2-3 hours, free)
  • North Avenue Beach (2-3 hours, free)
  • Total Estimated Costs: $95-240

Transportation

Chicago is a very walkable city with excellent public transportation options, including buses and trains. Visitors can also use ride-sharing services like Uber and Lyft. A 7-day unlimited Chicago Transit Authority (CTA) pass costs $33 and covers use of trains and buses.

Useful Tips

If you have more time in the city, add a visit to the Shedd Aquarium, the Field Museum, or a evening show at the Chicago Theatre. For those with less time, consider skipping the Art Institute of Chicago or the Navy Pier to focus on other must-see attractions. Additionally, wear comfortable shoes and dress in layers to be prepared for the city’s weather and long walking distances.

Airports

The main airport serving Chicago is O'Hare International Airport (ORD), located 17 miles northwest of Downtown Chicago. The airport is easily accessible by public transportation, taxi or ride-sharing services. Alternatively, the Midway International Airport (MDW) is located 10 miles from Downtown Chicago, also offers public transportation and taxi or ride-sharing services.

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