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USA

Chicago and Indianapolis (Self Drive)

6 to 9+ Nights from $878*
* This sample price: priced within the past 7 days for check-in on 3/1/2025. Choose your own arrival dates.

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This 6 night sample itinerary includes:

  • Rental Car for 4 days
  • Hotel for 3 nights in Chicago
  • Hotel for 3 nights in Indianapolis
  • Driving Time
    Chicago - Indianapolis: 3 hrs. approx.

Take the Midwest States of Illinois and Indiana into your own hands, travelling between these charming cities with a Rental Car. Start this trip in the sophisticated "Wind City"; Chicago (with its steely skyscrapers, museums and rocking festivals). Then, drive to Indiana and ends this trip, with a pleasant stay in "Indy" Indianapolis (the state capital, with its speeding race cars, plenty of green space, glistening waterways and remarkable memorials). This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.

Flexible Itinerary

  • Chicago, IL

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  • Indianapolis, IN

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USA

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Trip Summary

  • Chicago, IL
    Chicago, IL

    Chicago, on Lake Michigan in Illinois, is among the largest cities in the U.S. Famed for its bold architecture, it has a skyline punctuated by skyscrapers such as the iconic John Hancock Center, 1,451-ft. Willis Tower (formerly the Sears Tower) and the neo-Gothic Tribune Tower. The city is also renowned for its museums, including the Art Institute of Chicago with its noted Impressionist and Post-Impressionist works.

    Explore the Millenium Park, Willis Tower, Navy Pier, Shedd Aquarium, Grant Park, Cloud Gate, Field Museum, Chicago Riverwalk and much more.

  • Indianapolis, IN
    Indianapolis, IN

    Indianapolis claims to fame revolve mostly around sports. The Indianapolis 500, Brickyard 400 and the Mac Tools U.S. Nationals allow the city to boast the two largest single-day sporting events in the world and the world's largest drag race. Add in the Indianapolis Colts, the NBA Pacers and the NCAA headquarters, and it's easy to understand why sports can overshadow everything else the city has to offer.If you take time to look around, though, you'll find that Indianapolis's pride extends well beyond the racecourse.

    Explore the Indianapolis Zoo, Indiana State Museum, White River State Park, Fort Harrison State Park, Eagle Creek Park, Monument Circle, Indiana World War Memorial and much more.

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