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Lowest round trip fares by airline from Jacksonville and Chicago

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

Cheap flights from Jacksonville to Chicago

Cheap flights from Jacksonville to Chicago

Are you ready to book your flight, but feeling nervous about paying too much if the price drops? 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 a $50 CheapCash bonus, 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 Jacksonville to Chicago by signing up for exclusive email deals.

Packages from Jacksonville to Chicago

Hotels in Chicago

See all 1,399 Properties in Chicago
Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL
    3.5 out of 5.0
     
     
    3.9 out of 5 (29 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$129

    Congress Plaza Hotel$129
    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$86

      Hotel Essex Chicago$86
      Eurostars Magnificent Mile, previously Dana Hotel

      Eurostars Magnificent Mile, previously Dana Hotel

      660 North State Street, Chicago, IL
        4.0 out of 5.0
         
         
        4.5 out of 5 (28 reviews)

        Located in River North, this spa hotel is steps from Chinese Consulate and State Street. Chicago Water Tower and Tribune Tower are also within 10 minutes. Chicago ...

        Eurostars Magnificent Mile, previously Dana Hotel$117

        Eurostars Magnificent Mile, previously Dana Hotel$117
        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 Grant Park, Navy Pier, and Millennium Park. Art Institute of Chicago and Cloud Gate are also ...

          The St. Clair Hotel – Magnificent Mile$110

          The St. Clair Hotel – Magnificent Mile$110
          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$74

            Inn of Chicago$74
            Warwick Allerton - Chicago

            Warwick Allerton - Chicago

            701 North Michigan Avenue, Chicago, IL
              4.0 out of 5.0
               
               
              3.9 out of 5 (117 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$105

              Warwick Allerton - Chicago$105
              DoubleTree by Hilton Chicago - Magnificent Mile

              DoubleTree by Hilton Chicago - Magnificent Mile

              300 E Ohio St, Chicago, IL
                3.5 out of 5.0
                 
                 
                4.2 out of 5 (30 reviews)

                Located in Near North Side, this hotel is within a 10-minute walk of Michigan Avenue, Chicago Riverwalk, and Tribune Tower. Chicago Water Tower and Northwestern ...

                DoubleTree by Hilton Chicago - Magnificent Mile$104

                DoubleTree by Hilton Chicago - Magnificent Mile$104
                Wyndham Grand Chicago Riverfront

                Wyndham Grand Chicago Riverfront

                71 E Wacker Dr, Chicago, IL
                  4.0 out of 5.0
                   
                   
                  4.4 out of 5 (30 reviews)

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

                  Wyndham Grand Chicago Riverfront$161

                  Wyndham Grand Chicago Riverfront$161
                  The Whitehall Hotel

                  The Whitehall Hotel

                  105 E Delaware Pl, Chicago, IL
                    4.0 out of 5.0
                     
                     
                    3.8 out of 5 (145 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$94

                    The Whitehall Hotel$94
                    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$149

                      Palmer House a Hilton Hotel$149
                      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.