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Lowest round trip fares by airline from Colorado Springs and Chicago

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Cheap flights from Colorado Springs to Chicago

Cheap flights from Colorado Springs to Chicago

Are you ready to book your flight, but feeling nervous about paying too much if prices drop in a few days? Don't play the waiting game. Our Best Price Guarantee means if you see a better fare for the same flight, we'll give you the difference in CheapCash, plus $50 more in CheapCash, which you can use to save on your hotel reservation.

If you have a frequent flier account, add it to your reservation to earn miles. And don't worry about getting stuck in a middle seat. Choose your seats when you book, so you'll be right where you want to be on departure day.

Save Even More Time and Money With a Chicago Travel Package

Once your flights are booked, why start all over again searching for a cheap hotel? Book your flight and hotel together, and save yourself more than time and energy. You'll also be able to take advantage of discounts and coupons on your Chicago vacation that you can't get when you book flights and hotel separately.

Relax in Chicago With Confidence and Convenience

Going cheap doesn't mean giving up great service. Our agents are available 24/7 to help you find the right cheap flights and hotel, and to answer questions about your trip.

Need to grab a cheap travel deal while you're on the go? Download our mobile app, where you can search and book just like you would on your home computer. Stay in-the-know on great rates on flights from Colorado Springs to Chicago by signing up for exclusive email deals.

Packages from Colorado Springs to Chicago

Chicago vacations with economy flights

Hotels in Chicago

See all 1,825 Properties in Chicago
Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL
    3.5 out of 5.0
     
     
    3.8 out of 5 (27 reviews)

    Located in The Loop, this hotel is steps from Columbia College Chicago, Museum of Contemporary Photography, and Auditorium Building and Theatre. Fine Arts Building ...

    Congress Plaza Hotel$158

    Congress Plaza Hotel$158
    Hotel Essex Chicago

    Hotel Essex Chicago

    800 S Michigan Ave, Chicago, IL
      4.0 out of 5.0
       
       
      4.0 out of 5 (5 reviews)

      Located in The Loop, this hotel is steps from Lakefront Trail and Grant Park. State Street and Columbia College Chicago are also within 5 minutes. Harrison Station ...

      Hotel Essex Chicago$121

      Hotel Essex Chicago$121
      Warwick Allerton - Chicago

      Warwick Allerton - Chicago

      701 North Michigan Avenue, Chicago, IL
        4.0 out of 5.0
         
         
        3.9 out of 5 (116 reviews)

        This family-friendly Chicago hotel is located in the entertainment district, just steps from Northwestern Memorial Hospital and Michigan Avenue. Chicago Water ...

        Warwick Allerton - Chicago$120

        Warwick Allerton - Chicago$120
        Inn of Chicago

        Inn of Chicago

        162 E Ohio St, Chicago, IL
          3.0 out of 5.0
           
           
          3.5 out of 5 (35 reviews)

          Located in Near North Side, this beach hotel is within a 5-minute walk of Michigan Avenue, Tribune Tower, and Northwestern Memorial Hospital. Chicago Water Tower ...

          Inn of Chicago$94

          Inn of Chicago$94
          The Whitehall Hotel

          The Whitehall Hotel

          105 E Delaware Pl, Chicago, IL
            4.0 out of 5.0
             
             
            3.8 out of 5 (143 reviews)

            Located in Near North Side, this romantic hotel is steps from 900 North Michigan Shops, John Hancock Center, and Water Tower Place. Chicago Water Tower and Michigan ...

            The Whitehall Hotel$114

            The Whitehall Hotel$114
            Swissotel - Chicago

            Swissotel - Chicago

            323 E Wacker Dr, Chicago, IL
              4.5 out of 5.0
               
               
              4.4 out of 5 (36 reviews)

              Located in The Loop, this luxury hotel is within a 5-minute walk of Chicago Riverwalk and Michigan Avenue. Grant Park and Tribune Tower are also within 10 minutes. ...

              Swissotel - Chicago$159

              Swissotel - Chicago$159
              Palmer House a Hilton Hotel

              Palmer House a Hilton Hotel

              17 E Monroe St, Chicago, IL
                4.0 out of 5.0
                 
                 
                4.0 out of 5 (54 reviews)

                Located in The Loop, this spa hotel is within a 5-minute walk of Art Institute of Chicago and Millennium Park. Chicago Theatre and Willis Tower are also within ...

                Palmer House a Hilton Hotel$176

                Palmer House a Hilton Hotel$176
                Sofitel Chicago Magnificent Mile

                Sofitel Chicago Magnificent Mile

                20 E Chestnut St, Chicago, IL
                  4.5 out of 5.0
                   
                   
                  4.7 out of 5 (18 reviews)

                  Located in Near North Side, this luxury hotel is within a 5-minute walk of State Street, John Hancock Center, and Water Tower Place. Chicago Water Tower and ...

                  Sofitel Chicago Magnificent Mile$142

                  Sofitel Chicago Magnificent Mile$142
                  Hotel Julian

                  Hotel Julian

                  168 N Michigan Avenue, Chicago, IL
                    4.0 out of 5.0
                     
                     
                    5.0 out of 5 (3 reviews)

                    Located in The Loop, this hotel is steps from Chicago Theatre, Grant Park, and State Street. Chicago Cultural Center and Ford Center for the Performing Arts ...

                    Hotel Julian$149

                    Hotel Julian$149
                    Renaissance Chicago O'Hare Suites Hotel

                    Renaissance Chicago O'Hare Suites Hotel

                    8500 West Bryn Mawr Avenue, Chicago, IL
                      4.0 out of 5.0
                       
                       
                      4.6 out of 5 (11 reviews)

                      Located in O'Hare, this hotel is within 3 mi (5 km) of Rivers Casino, Donald E. Stephens Convention Center, and Rosemont Theatre. Fashion Outlets of Chicago ...

                      Renaissance Chicago O'Hare Suites Hotel$95

                      Renaissance Chicago O'Hare Suites Hotel$95
                      Map

                      *Savings based on all holiday package bookings with Flight + Hotel on CheapTickets.com from January through December 2017, 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. For Free Flight or 100% Off Flight deals, package savings is greater than or equal to the current cost of one component, when both are priced separately.

                      *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.