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Due to coronavirus (COVID-19) travel advisories, some destinations may be unavailable for certain dates. Find out more.
182 customers have saved 100% on their flight when booking a Flight + Hotel together this year!
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182 customers have saved 100% on their flight when booking a Flight + Hotel together this year!

Chicago vacations

3-night Chicago vacations

4-night Chicago vacations

5-night Chicago vacations

Cheap Hotels for your vacation in Chicago

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

85 East Wacker Drive, Chicago, IL
    4.5 out of 5.0
     
     
    4.9 out of 5 (11 reviews)

    Located in The Loop, this luxury hotel is steps from Chicago Riverwalk and Michigan Avenue. Grant Park and Chicago Theatre are also within 10 minutes. Clark-Lake ...

    $98

    The Godfrey Hotel Chicago

    The Godfrey Hotel Chicago

    127 West Huron, at LaSalle, Chicago, IL
      4.5 out of 5.0
       
       
      4.3 out of 5 (9 reviews)

      Located in River North, this luxury hotel is within a 10-minute walk of State Street, Michigan Avenue, and Northwestern Memorial Hospital. Chicago Riverwalk ...

      $135

      Chicago Vacation Deal FAQ's

      Where to find Chicago package deals?

      On CheapTickets, you can find package deals in Chicago as low as $175!

      When is peak season in Chicago?

      July, June, May are very popular times to visit Chicago.

      When is the best time to visit Chicago?

      If you're looking for cheap vacations to Chicago, January is the best time to visit Chicago.

      When is the worst time time to visit Chicago?

      Prices for Chicago vacations can peak during October.

      When is low season in Chicago?

      We have found October, December, November to be the least-crowded time of the year to visit Chicago.

      ^Savings based on all package bookings made with Flight + Hotel on CheapTickets.com from January 1, 2019 to December 31, 2019, as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages. 

      *Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.