Beginning of main content
Round Trip Icon
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Search over 895,000 properties worldwide and 550 airlines worldwide.

Search over a million flights, hotels, packages, and more

No Expedia cancellation fee to change or cancel almost any hotel reservation.

Find cheap flights from Chicago (ORD) to Boston (BOS)

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

Hotels by Airports near

See all 952 properties in Logan Intl.
Hilton Boston Logan Airport C$194
Hilton Boston Logan Airport

Hilton Boston Logan Airport

One Hotel Drive, Boston
    of 5, from 4,290 reviews
    4.0 out of 5.0

    This hotel is connected to Logan Airport terminals by a climate-controlled skybridge. A complimentary 24-hour airport shuttle is also available.

    Hyatt Regency Boston Harbor C$156
    Hyatt Regency Boston Harbor

    Hyatt Regency Boston Harbor

    101 Harborside Drive, Boston
      of 5, from 2,281 reviews
      4.0 out of 5.0

      This 15-story hotel is located on Boston's Harbor with skyline views of downtown, adjacent to Logan International Airport and a water taxi stop; Charlestown Navy Yard and Museum Wharf are just 2 miles away.

      Boston Park Plaza C$134
      Boston Park Plaza

      Boston Park Plaza

      50 Park Plaza at Arlington Street, Boston
        of 5, from 3,763 reviews
        4.0 out of 5.0

        Located in historic Back Bay, this hotel just completed a $100 million dollar renovation, and is 3 miles from Logan International Airport and 200 yards from the Boston Common and Public Garden. The hotel is easily accessible to Newbury Street shopping.

        Embassy Suites Boston Logan Airport C$171
        Embassy Suites Boston Logan Airport

        Embassy Suites Boston Logan Airport

        207 Porter St, Boston
          of 5, from 3,503 reviews
          3.5 out of 5.0

          Embassy Suites Boston Logan Airport is less than 2 miles from the airport, 3 miles from Faneuil Hall, and 4 miles from downtown Boston and the New England Aquarium.

          Seaport Hotel C$201
          Seaport Hotel

          Seaport Hotel

          1 Seaport Lane, Boston
            of 5, from 3,911 reviews
            4.0 out of 5.0

            Atop Commonwealth Pier, near the Seaport World Trade Center and the Boston Convention & Exhibit Center, this hotel is one mile from the Financial District, three miles from Logan Airport, and a 10-minute bus ride from South Station.

            The Godfrey Hotel Boston C$178
            The Godfrey Hotel Boston

            The Godfrey Hotel Boston

            505 Washington Street, Boston
              of 5, from 1,958 reviews
              4.0 out of 5.0

              Located in Downtown Boston, this boutique hotel is steps from Boston Opera House and Orpheum Theater. Boston Common and Boston Public Garden are also within 10 minutes. Downtown Crossing Station and Park St. Station are within a 5-minute walk.

              Boston Omni Parker House Hotel C$136
              Boston Omni Parker House Hotel

              Boston Omni Parker House Hotel

              60 School St, Boston
                of 5, from 5,501 reviews
                4.0 out of 5.0

                Located on Freedom Trail in downtown Boston, this hotel is 3 blocks from Quincy Market, 2 from the State House and Boston Common, and adjacent to the Financial District. The hotel is 10 minutes from Logan International Airport by car and 20 minutes by train for only USD 2 each way.

                Revere Hotel Boston Common C$184
                Revere Hotel Boston Common

                Revere Hotel Boston Common

                200 Stuart St, Boston
                  of 5, from 5,265 reviews
                  4.0 out of 5.0

                  The Revere Hotel is at the edge of the Theatre District, 1 block from the Arlington "T" Station and 2 blocks from Boston Common and the Public Garden.



                  Cheap ORD to BOS Flights

                  • Question : How long does it take to fly from Chicago to Boston?
                    Answer : When taking off from ORD to BOS, it will take two hours and 14 minutes on average. Remember, there is a one hour time difference.
                  • Question : What is the cheapest date to fly to Boston?
                    Answer : As of Jan 14th, the best day for deals to Boston (BOS) is Feb 1st. A ticket will put you out $177, which is 19% less than this route's average price.
                  • Question : How long is the flight from ORD to BOS?
                    Answer : If you're able to take the direct flight (which is offered by American Airlines), you will be able to leave ORD at 9:42 PM CST and get to BOS at 12:50 AM EST (two hours and eight minutes). Remember, there is a one hour time change.
                  • Question : What is the cheapest day to fly?
                    Answer : The cheapest day to fly from Chicago to Boston is on Thursday. So, if you are trying to save some money on your next getaway look for flights on that day.
                  • Question : Is there a day of the week that has more departure times to choose from than other days?
                    Answer : With 41 total flight time options, Sunday provides the most flexibility from ORD to BOS. However, with 34 flight times, Saturday doesn't offer quite as many options when finding that perfect departure time.
                  • Question : Can I change the date of my flight?
                    Answer : You sure can switch your departure or arrival date and you may save yourself some money by changing when you leave. The lowest-cost day to fly in January is Thursday. You may be thinking you're missing out taking off a day early, but we think that you are just adding saving for your next trip. A dollar saved is a holiday earned.
                  • Question : Which airline has the least delays from Chicago to Boston?
                    Answer : Booking with Republic Airlines means you will arrive to Boston pretty close to the time your ticket states. In fact, this airline has an 87% average for getting there on time.

                  Dec 29, 2016

                  luggage was 24 hours late