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Chicago and Naperville (Self Drive)

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This 5 night sample itinerary includes:

  • Flight into and out of Chicago
  • Rental Car for 3 days
  • Hotel for 3 nights in Chicago
  • Hotel for 2 nights in Naperville
  • Driving Time
    Chicago - Naperville: 55 mins. approx.
    Naperville - Chicago Airport: 45 mins. approx.

Enjoy this Self-Drive Package to venture through the "Land of Lincoln'; Illinois, discovering these two charming cities. With a Rental Car, combine and visit; Chicago (renowned for its bold architecture, like the "Sears Tower", museums and festivals). After that, have a wonderful stay in Naperville; with an "expected beach surprise": The Naperville's Centennial Beach (historic double quarry alongside the DuPage River, with a white sand beach). The site also offer an important Outdoor History Museum, with a collection of historical buildings and structures from the historic Naperville settlement.

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Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
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Flexible Itinerary

  • Chicago, IL

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  • Naperville, IL

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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.

  • Naperville, IL
    Naperville, IL

    Naperville is filled with excitement and activities for the whole family, one of the largest, wealthiest, and most popular suburbs 35 miles west of the Windy City. Known as one of the best places to live and one of the safest, the `crown jewel` of Illinois. Naperville Riverwalk runs through the heart of the city decorated with colorful art, quaint local boutiques, and delicious authentic eateries, the two-mile path connects the city with wide-open green spaces of the Naper Settlement.

    Explore The Morton Arboretum, Cantigny Park, Naper Settlement, Centennial Beach, DuPage Children`s Museum, Naperville Riverwalk, Bright Side Theatre, and so much more!

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