14 days in Chicago Itinerary

14 days in Chicago Itinerary

Created using Inspirock Chicago attractions planner

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1
Chicago
— 13 nights

13
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Change things up with these side-trips from Chicago: Whiskey Acres Distilling Co. (in DeKalb), Rotary Botanical Gardens (in Janesville) and South Bend (Basilica of the Sacred Heart & University of Notre Dame). There's much more to do: admire the masterpieces at The Art Institute of Chicago, take in the waterfront at Navy Pier, meet the residents at Shedd Aquarium, and don't miss a visit to Skydeck Chicago - Willis Tower.

To see maps, reviews, and other tourist information, you can read our Chicago online trip itinerary planner .

If you are flying in from Puerto Rico, the closest major airports are Chicago Midway International Airport, Chicago O'Hare International Airport and South Bend Regional Airport. In September, plan for daily highs up to 30°C, and evening lows to 19°C. Wrap up your sightseeing on the 10th (Thu) early enough to travel back home.

Things to do in Chicago

Museums Parks Historic Sites

Side Trips

Oak Park, Milwaukee, Wheaton, South Bend, Whiskey Acres Distilling Co.
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Millennium Park ©
Millennium Park
Museum of Science and Industry ©
Museum of Science and Industry

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