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Lowest round trip fares by airline from Denver and Chicago

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

Cheap flights from Denver to Chicago

Cheap flights from Denver to Chicago

Whether you’re traveling to Chicago from Denver for pleasure or for work, take advantage of the Windy City's abundance of local attractions while you're there. Chicago offers many interesting places to see, and a rental car is your key to exploring this sprawling metropolis. You may want to visit the Field Museum of Natural History, or Lincoln Park, which houses a famous zoo, beaches, museums and even a golf course.

Key Facts

After picking up your rental car at Chicago Midway International Airport (MDW), you can use the airport's free Wi-Fi to scout out the best routes to your destination. Hyde Park and its Museum of Science and Industry, the biggest in the Western Hemisphere, features exhibits from a German submarine, to the Vortex Show.

Chicago nightlife offers everything from Broadway shows to jazz and blues clubs. Nearby, you can visit the John G. Shedd Aquarium, or the Brookfield Zoo to relax. Another great option is to head for the Navy Pier to enjoy its carnival-like atmosphere, right on Lake Michigan.

Hints and Tips

Your direct flight from Denver International Airport (DEN) to Chicago should arrive in about two hours. Midway does not have a car rental facility on-site, but travelers can hop on the CTA's Orange Line for a quick ride into the city to pick up their vehicle.

Packages from Denver to Chicago

Hotels in Chicago

See all 1,635 Properties in Chicago

Estimated price for 1 night/2 adults

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL
    3.5 out of 5.0
     
     
    3.8 out of 5 (20 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$115

    Aug 11 - Aug 12

    Congress Plaza Hotel$115
    Hyatt Regency Chicago

    Hyatt Regency Chicago

    151 East Wacker Dr, Chicago, IL
      4.0 out of 5.0
       
       
      4.2 out of 5 (89 reviews)

      Located in The Loop, this eco-friendly hotel is steps from Chicago Riverwalk and Michigan Avenue Bridge. Chicago Theatre and Millennium Park are also within ...

      Hyatt Regency Chicago$199

      Aug 15 - Aug 16

      Hyatt Regency Chicago$199
      Travelodge by Wyndham Downtown Chicago

      Travelodge by Wyndham Downtown Chicago

      65 E Harrison St, Chicago, IL
        2.0 out of 5.0
         
         
        3.0 out of 5 (39 reviews)

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

        Travelodge by Wyndham Downtown Chicago$95

        Jul 31 - Aug 1

        Travelodge by Wyndham Downtown Chicago$95
        Hotel Essex Chicago

        Hotel Essex Chicago

        800 S Michigan Ave, Chicago, IL
          4.0 out of 5.0
           
           
          4.0 out of 5 (1 reviews)

          Located in The Loop, this hotel is within a 5-minute walk of Lakefront Trail, State Street, and Columbia College Chicago. Grant Park and Buckingham Fountain ...

          Hotel Essex Chicago$113

          Aug 11 - Aug 12

          Hotel Essex Chicago$113
          Central Loop Hotel

          Central Loop Hotel

          111 West Adams Street, Chicago, IL
            4.0 out of 5.0
             
             
            4.2 out of 5 (47 reviews)

            Located in The Loop, this boutique hotel is within a 5-minute walk of Chicago Board of Trade Building and State Street. Willis Tower and Skydeck Ledge are also ...

            Central Loop Hotel$116

            Jul 28 - Jul 29

            Central Loop Hotel$116
            Warwick Allerton - Chicago

            Warwick Allerton - Chicago

            701 North Michigan Avenue, Chicago, IL
              4.0 out of 5.0
               
               
              3.9 out of 5 (115 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$112

              Jul 28 - Jul 29

              Warwick Allerton - Chicago$112
              Kinzie Hotel

              Kinzie Hotel

              20 W Kinzie St, Chicago, IL
                4.0 out of 5.0
                 
                 
                4.5 out of 5 (59 reviews)

                Located in River North, this hotel is steps from House of Blues Chicago and State Street. Tribune Tower and Wrigley Building are also within 10 minutes. Grand ...

                Kinzie Hotel$138

                Aug 18 - Aug 19

                Kinzie Hotel$138
                The St. Clair Hotel – Magnificent Mile

                The St. Clair Hotel – Magnificent Mile

                162 East Ontario Street, Chicago, IL
                  2.5 out of 5.0
                   
                   
                  4.0 out of 5 (5 reviews)

                  Located in Near North Side, this hotel is within 1 mi (2 km) of Navy Pier, Millennium Park, and Art Institute of Chicago. Cloud Gate and Grant Park are also ...

                  The St. Clair Hotel – Magnificent Mile$130

                  Aug 11 - Aug 12

                  The St. Clair Hotel – Magnificent Mile$130
                  Hilton Chicago- Michigan Ave Cultural Mile

                  Hilton Chicago- Michigan Ave Cultural Mile

                  720 S Michigan Ave, Chicago, IL
                    4.0 out of 5.0
                     
                     
                    4.3 out of 5 (26 reviews)

                    Located in The Loop, this historic hotel is within a 5-minute walk of Columbia College Chicago and Grant Park. Art Institute of Chicago and Millennium Park are ...

                    Hilton Chicago- Michigan Ave Cultural Mile$162

                    Jul 25 - Jul 26

                    Hilton Chicago- Michigan Ave Cultural Mile$162
                    The Whitehall Hotel

                    The Whitehall Hotel

                    105 E Delaware Pl, Chicago, IL
                      4.0 out of 5.0
                       
                       
                      3.8 out of 5 (141 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$106

                      Jul 28 - Jul 29

                      The Whitehall Hotel$106
                      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.