phone_icon

Destinations

Main Menu

My Booking

Main Menu

About Us

Main Menu
USA

Chicago and the Lake Michigan Shore (Self Drive)

7 Nights from $1,645*
* Sample price: priced within the past 7 days for a 5/31/2026 arrival, departing Miami MIA (FL), US. Choose departure city, cabin and dates.

Customize and Book

Add Outbound & Return Flights

This 7 night sample itinerary includes:

  • Flight into Chicago and out of Milwaukee
  • 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).

What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
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
Live phone and chat support

USA

Customer Reviews

Customer Reviews

  • You can now

    Stagger

    your payment!