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Chicago and the Lake Michigan Shore (Self Drive)

7 to 10+ Nights from $1,338*
* This sample price: priced within the past 7 days for check-in on 3/8/2025. Choose your own arrival dates.

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This 7 night sample itinerary includes:

  • Rental Car for 8 days
  • Hotel for 3 nights in Chicago, IL
  • Hotel for 2 nights in Illinois State Beach, IL
  • Hotel for 2 nights in Lake Michigan Shore South, WI
  • Driving Time
    Chicago, IL - Illinois State Beach, IL: 1 hrs 3 mins approx.
    Illinois State Beach, IL- Lake Michigan Shore South, WI: 3 hr. 8 mins. approx.

This self-drive, independent vacation package will introduce you to Illinois and Wisconsin. Visit Chicago, on Lake Michigan in also called `The wind city ‘and it will blow you away with its steely skyscrapers, museums and rocking festivals, then, drive to Illinois State Beach and Lake Michigan Shore South (sprawling waterfront of activity and beauty, Traveling the towns throughout the Shore you will find shopping destinations, to world-class golf courses, to family-friendly attractions and casinos). 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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  • Illinois Beach State Park, IL

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  • Lake Michigan Shore South, WI

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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.

  • Illinois Beach State Park, IL
    Illinois Beach State Park, IL

    The Illinois Beach State Park offers the best of Lake County boasting stunning scenic landscapes including 6 ½ miles of sandy shoreline on Lake Michigan, 4,160 acres of park decorated with unique flora, breathtaking beauty and a vast array of scenic recreational opportunities. A myriad of trails crisscrosses through the park where walkers and cyclists can roam, access to the largest marina in Illinois, beaches for swimming, and campsites.

    Explore the Six Flags Great America, Great Wolf Lodge | Illinois, Bowen Park, Kenosha Public Museum, and more.

  • Lake Michigan Shore South, WI
    Lake Michigan Shore South, WI

    The Lake Michigan shoreline south of Milwaukee before the state line with Illinois is home to two major Wisconsin cities: Kenosha and Racine, respectively the fourth and fifth-largest cities in the state. Fun fact, Kenosha is one of the smallest cities in the U.S. to have its own streetcar system. Then there`s Racine, well-known for its public beach, one of the most popular on Lake Michigan, and for historic Wind Point Lighthouse, one of the oldest active lighthouses on the Great Lakes.

    Explore the Wind Point Lighthouse, Racine Art Museum, Civil War Museum, Racine Zoo, Dinosaur Discovery Museum, Kenosha Public Museum, Southport Light Station Museum, Racine North Beach, Racine Heritage Museum, Charles A. Wustrum Museum of Fine Arts, and so much more!

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