19 days in Indianapolis & Chicago Itinerary

19 days in Indianapolis & Chicago Itinerary

Created using Inspirock United States trip itinerary planner

Make it your trip
1
Indianapolis
— 6 nights
Drive
2
Chicago
— 12 nights
Drive

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Indianapolis

— 6 nights

Circle City

Indiana's capital and most populous city, Indianapolis is best known for its racecar events and impressive museums, and as the hometown of Kurt Vonnegut.
Get out of town with these interesting Indianapolis side-trips: Louisville (The Belvedere, Louisville Slugger Museum & Factory, &more), Cincinnati (Smale Riverfront Park & JACK Cincinnati Casino) and Zaharakos Ice Cream Parlor and Museum (in Columbus). There's still lots to do: test your team's savvy at popular escape rooms, let little ones run wild at Arbuckle Acres Park, see the interesting displays at The Eiteljorg Museum, and don't miss a visit to USS Indianapolis Memorial.

To see reviews, traveler tips, more things to do, and tourist information, refer to the Indianapolis route planner.

The Route module can give you travel options from your home to Indianapolis. Expect a daytime high around 67°F in October, and nighttime lows around 48°F. Finish your sightseeing early on the 12th (Sat) to allow enough time to drive to Chicago.

Things to do in Indianapolis

Museums · Fun & Games · Parks · Historic Sites

Side Trips

Chicago

— 12 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Venture out of the city with trips to ZumBier (in Waukegan), Little Red Schoolhouse (in Willow Springs) and Milwaukee (Chudnow Museum of Yesteryear & Harley-Davidson Museum). There's much more to do: admire the masterpieces at The Art Institute of Chicago, get up close and personal with brilliant marine life at Shedd Aquarium, learn more about the world around you at Field Museum, and admire nature's wide array of creatures at Lincoln Park Zoo.

To see ratings, more things to do, maps, and more tourist information, you can read our Chicago journey planning site.

Traveling by car from Indianapolis to Chicago takes 3 hours. Alternatively, you can fly; or take a bus. The time zone difference moving from Eastern Standard Time (EST) to Central Standard Time (CST) is minus 1 hour. October in Chicago sees daily highs of 65°F and lows of 49°F at night. Finish your sightseeing early on the 24th (Thu) so you can drive back home.

Things to do in Chicago

Museums · Parks · Fun & Games · Shopping

Side Trips