48 Hours in Chicago: The Ultimate Weekend Itinerary







48 Hours in Chicago: The Ultimate Weekend Itinerary

48 Hours in Chicago: The Ultimate Weekend Itinerary

Travel photo of Chicago

Day 1

Morning: Start your day with a visit to Millennium Park to see the iconic Cloud Gate sculpture, also known as “The Bean”. Don’t forget to take some selfies and enjoy the beautiful views of the city skyline.

Afternoon: Head to the Art Institute of Chicago, one of the oldest and largest art museums in the United States. Explore its impressive collection of artworks, including pieces by famous artists such as Grant Wood and Edward Hopper.

Evening: For dinner, make your way to the vibrant neighborhood of Wicker Park and indulge in some delicious deep-dish pizza at Lou Malnati’s Pizzeria. After dinner, catch a show at the famous Second City comedy club for some laughs.

Day 2

Morning: Start your day with a stroll along the Chicago Riverwalk and admire the city’s stunning architecture. You can also take a river cruise to learn more about the history of Chicago’s buildings.

Afternoon: Visit Navy Pier, a popular tourist attraction with shops, restaurants, and entertainment options. Don’t miss the Centennial Wheel for panoramic views of the city and Lake Michigan.

Evening: End your weekend in Chicago with a visit to the John Hancock Center’s 360 Chicago Observation Deck. Enjoy breathtaking views of the city at sunset before heading to a local jazz club for some live music.

Travel Tips:

  • Chicago is known for its unpredictable weather, so make sure to pack layers and check the forecast before your trip.
  • Public transportation in Chicago is convenient and easy to use, so consider getting a Ventra card for unlimited rides on buses and trains.
  • Don’t forget to try some Chicago-style hot dogs and Garrett Popcorn while you’re in the city!



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