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Lowest round trip fares by airline from Boston and Chicago

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

Cheap flights from Boston to Chicago

Find cheap tickets for flights from Boston to Chicago at CheapTickets. Why shop around when the low fares are handed to you?

Logan International Airport (BOS) is presently the only airport with bargain commercial Boston to Chicago flights via American Airlines. A 12-year top-to-bottom update project by Massachusetts Port Authority (Massport) was concluded only six years ago. Passengers departing on domestic flights from Boston to Chicago will most likely notice the parking garage, terminals, and arrival and departure roadway improvements. American Airlines operates an Admirals Club in Terminal B North for passengers waiting to board budget Boston to Chicago flights, which usually depart from Gates B22-36. Logan strives to improve the customer experience, and has been noted for the variety of choices available for arrival and departure transport, and its on-time departure record.

O'Hare International Airport (ORD) and Midway International Airport (MDW) both receive incoming low cost flights from Boston to Chicago. Discount carriers JetBlue Airways and Spirit Airlines share gate 3L with American Airlines, which also utilizes Gates 3H and 3K. United Airlines and their affiliate United Express and subcontractor Shuttle America keep to Gates 1B and 1C. Southwest Airlines Boston to Chicago flights arrive at Midway's A and B concourses. Travelers exiting Midway enjoy convenient access to the central business district and Loop through Stevenson Expressway and Chicago Transit Authority's (CTA) Orange Line elevated trains. CTA also uses the Midway station for bus service to several stops in the vicinity.

Packages from Boston to Chicago

Hotels in Chicago

See all 1,633 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 (21 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$102

    Aug 19 - Aug 20

    Congress Plaza Hotel$102
    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$159

      Aug 15 - Aug 16

      Hyatt Regency Chicago$159
      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 30 - Jul 31

        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$105

              Aug 11 - Aug 12

              Warwick Allerton - Chicago$105
              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$127

                Aug 18 - Aug 19

                Kinzie Hotel$127
                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 18 - Aug 19

                  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

                    Aug 12 - Aug 13

                    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$117

                      Jul 28 - Jul 29

                      The Whitehall Hotel$117
                      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.