phone_icon

Destinations

Main Menu

My Booking

Main Menu

About Us

Main Menu
USA

Chicago Getaway

5.0 out of 5 stars
1 Customer Feedbacks 1 Customer Feedbacks
4 to 6+ Nights from $582*
* Sample price: priced within the past 7 days for a 5/23/2025 arrival, departing Kansas City MCI (MO), US. Choose departure city, cabin and dates.

Customize and Book

Add Outbound & Return Flights

This 4 night sample itinerary includes:

  • Flight into and out of Chicago
  • Rental Car for 5 days
  • Hotel for 4 nights in Chicago

This self-drive, independent vacation package will introduce you Illinois. 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.

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

Flexible Itinerary

  • Chicago, IL

    no image
USA

Customer Reviews

5.0 out of 5 stars

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.

  • You can now

    Stagger

    your payment!