2 days in Chicago & Wisconsin Dells Itinerary

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.

Start off your visit on the 17th (Sat): take in panoramic vistas at Skydeck Chicago - Willis Tower, then walk around Millennium Park, then explore the world behind art at The Art Institute of Chicago, and finally don't miss a visit to Buckingham Fountain.

For maps, more things to do, where to stay, and other tourist information, go to the Chicago travel route planner.

New York City to Chicago is an approximately 5-hour flight. You can also drive; or take a bus. Due to the time zone difference, you'll gain 1 hour traveling from New York City to Chicago. In October, Chicago is little chillier than New York City - with highs of 65°F and lows of 49°F. Finish your sightseeing early on the 17th (Sat) to allow enough time to drive to Wisconsin Dells.

Named after a nearby scenic gorge famous for its steep sandstone formations, Wisconsin Dells features more than 20 water parks, making it one of the most popular vacation areas in this region.

On the 18th (Sun), kick your exploration up a notch at some of the top local zipline courses and adventure parks, go for a charming ride with Lost Canyon Tours, and then don't miss a visit to Carr Valley Cheese.

Inspirock's itinerary builder makes planning a Wisconsin Dells trip simple and quick.

You can drive from Chicago to Wisconsin Dells in 3.5 hours. Alternatively, you can take a train; or do a combination of flight and train. Traveling from Chicago in October, expect Wisconsin Dells to be a bit cooler, temps between 60°F and 41°F. Wrap up your sightseeing by early afternoon on the 18th (Sun) to allow time for travel back home.