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Lowest round trip fares by airline from Santa Barbara and Chicago

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

Cheap flights from Santa Barbara to Chicago

Cheap flights from Santa Barbara 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 Santa Barbara to Chicago by signing up for exclusive email deals.

Hotels in Chicago

See all 1,821 Properties in Chicago
Hyatt Regency Chicago

Hyatt Regency Chicago

151 East Wacker Dr, Chicago, IL
    4.0 out of 5.0
     
     
    4.2 out of 5 (91 reviews)

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

    Hyatt Regency Chicago$90

    Hyatt Regency Chicago$90
    Warwick Allerton - Chicago

    Warwick Allerton - Chicago

    701 North Michigan Avenue, Chicago, IL
      4.0 out of 5.0
       
       
      3.9 out of 5 (118 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$86

      Warwick Allerton - Chicago$86
      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$95

        Swissotel - Chicago$95
        Radisson Blu Aqua Hotel Chicago

        Radisson Blu Aqua Hotel Chicago

        221 N Columbus Dr, Chicago, IL
          4.5 out of 5.0
           
           
          4.6 out of 5 (9 reviews)

          Located in The Loop, this luxury hotel is within a 5-minute walk of Chicago Riverwalk, Grant Park, and Aon Center. Chicago Theatre and Chicago Cultural Center ...

          Radisson Blu Aqua Hotel Chicago$130

          Radisson Blu Aqua Hotel Chicago$130
          Hilton Chicago O'Hare Airport

          Hilton Chicago O'Hare Airport

          Ohare International Airport, Chicago, IL
            4.0 out of 5.0
             
             
            4.0 out of 5 (20 reviews)

            Located in O'Hare, this hotel is within 6 mi (10 km) of Fashion Outlets of Chicago, Donald E. Stephens Convention Center, and Rosemont Theatre. Allstate Arena ...

            Hilton Chicago O'Hare Airport$110

            Hilton Chicago O'Hare Airport$110
            La Quinta Inn & Suites by Wyndham Chicago Downtown

            La Quinta Inn & Suites by Wyndham Chicago Downtown

            1 S Franklin Street, Chicago, IL
              3.0 out of 5.0
               
               
              4.8 out of 5 (8 reviews)

              Located in The Loop, this hotel is within a 5-minute walk of Willis Tower and Skydeck Ledge. Chicago Riverwalk and Merchandise Mart are also within 10 minutes. ...

              La Quinta Inn & Suites by Wyndham Chicago Downtown$84

              La Quinta Inn & Suites by Wyndham Chicago Downtown$84
              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$89

                Eurostars Magnificent Mile, previously Dana Hotel$89
                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 (32 reviews)

                  Located in The Loop, this historic hotel is within a 10-minute walk of Grant Park and Art Institute of Chicago. Millennium Park and Field Museum of Natural History ...

                  Hilton Chicago- Michigan Ave Cultural Mile$95

                  Hilton Chicago- Michigan Ave Cultural Mile$95
                  Palmer House a Hilton Hotel

                  Palmer House a Hilton Hotel

                  17 E Monroe St, Chicago, IL
                    4.0 out of 5.0
                     
                     
                    3.9 out of 5 (58 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$89

                    Palmer House a Hilton Hotel$89
                    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$75

                      Congress Plaza Hotel$75
                      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.