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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 1,621 Properties in Chicago

Estimated price for 1 night/2 adults

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$90

    Jun 30 - Jul 1

    Hotel Essex Chicago$90
    Congress Plaza Hotel

    Congress Plaza Hotel

    520 South Michigan Avenue, Chicago, IL
      3.5 out of 5.0
       
       
      3.9 out of 5 (17 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$89

      Jul 1 - Jul 2

      Congress Plaza Hotel$89
      Hyatt Regency Chicago

      Hyatt Regency Chicago

      151 East Wacker Dr, Chicago, IL
        4.0 out of 5.0
         
         
        4.2 out of 5 (86 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$108

        Jun 30 - Jul 1

        Hyatt Regency Chicago$108
        Hyatt Regency McCormick Place

        Hyatt Regency McCormick Place

        2233 S Martin Luther King Dr, Chicago, IL
          4.0 out of 5.0
           
           
          3.6 out of 5 (21 reviews)

          Located in South Loop, this eco-friendly hotel is within a 5-minute walk of McCormick Place and Wintrust Arena. Lakefront Trail and Soldier Field are also within ...

          Hyatt Regency McCormick Place$108

          Jun 30 - Jul 1

          Hyatt Regency McCormick Place$108
          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$80

            Jun 30 - Jul 1

            Central Loop Hotel$80
            Wyndham Grand Chicago Riverfront

            Wyndham Grand Chicago Riverfront

            71 E Wacker Dr, Chicago, IL
              4.0 out of 5.0
               
               
              4.5 out of 5 (27 reviews)

              Located in The Loop, this romantic hotel is within a 5-minute walk of Chicago Riverwalk, Chicago Theatre, and Michigan Avenue. Tribune Tower and Wrigley Building ...

              Wyndham Grand Chicago Riverfront$101

              Jul 1 - Jul 2

              Wyndham Grand Chicago Riverfront$101
              River Hotel

              River Hotel

              75 East Wacker Drive, Chicago, IL
                4.0 out of 5.0
                 
                 
                4.2 out of 5 (39 reviews)

                Located in The Loop, this hotel is steps from Chicago Riverwalk and Michigan Avenue. Tribune Tower and Chicago Theatre are also within 10 minutes. Clark-Lake ...

                River Hotel$80

                Jul 1 - Jul 2

                River Hotel$80
                Travelodge by Wyndham Downtown Chicago

                Travelodge by Wyndham Downtown Chicago

                65 E Harrison St, Chicago, IL
                  2.0 out of 5.0
                   
                   
                  2.9 out of 5 (38 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

                  Jun 27 - Jun 28

                  Travelodge by Wyndham Downtown Chicago$95
                  The Whitehall Hotel

                  The Whitehall Hotel

                  105 E Delaware Pl, Chicago, IL
                    4.0 out of 5.0
                     
                     
                    3.8 out of 5 (140 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$76

                    Jul 1 - Jul 2

                    The Whitehall Hotel$76
                    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 (52 reviews)

                      Located in The Loop, this spa hotel is within a 5-minute walk of State Street, Art Institute of Chicago, and Millennium Park. Chicago Cultural Center and Ford ...

                      Palmer House a Hilton Hotel$110

                      Jul 1 - Jul 2

                      Palmer House a Hilton Hotel$110
                      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.

                      Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other CheapTickets users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

                      Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $75 service fee charged by CheapTickets.

                      Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.