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Cheap Flights From Boston, Massachusetts To Chicago, Illinois
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Airfare Details for flights from Boston to Chicago

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Sorry this deal is over or has been sold out! But here’s another great Airfarewatchdog verified fare for this route!

$202 RT flight from Boston to Chicago (BOS-ORD)

  • Airline(s):
    American, United
  • Seats are:
    Limited Availability
  • More Details:
    Nonstop Incl. All Taxes
  • Last Updated:
    Sunday, May 19, 2013
  • Our Notes:
    CheapAir Will Include A $9.95 Booking Fee.
All mandatory taxes/fees are included in the price. Tax-inclusive fare may be a few dollars higher or lower depending on the airport you connect through, if any. Baggage fees, if applicable, and other optional fees are not included.

Our Dealhounds found this airfare using flexible date search. This means we searched a range of dates to find you the best price.

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Reviews

Reviews for Boston to Chicago (BOS-ORD)

based on 5 reviews
Flown this route before? Write a review

    1. Flight Rating

    2. Check-in Experience:

    3. In-flight Service:

    4. Seat Comfort:

    “Very good”

    by colonial on October 21, 2010

    Flight from Boston to Chicago

    Airline:
    JetBlue
    RT/OW
    Round Trip
    Number of Stops:
    No stops
    Date of Flight:
    October 2010
    Seat Class:
    economy

    The flights took off on time and were very smooth and landed early. It was a no hassle good trip.Very pleasant experience.

    1. Flight Rating

    2. Check-in Experience:

    3. In-flight Service:

    4. Seat Comfort:

    “What one expects”

    by smilinal on September 3, 2010

    Flight from Boston to Chicago

    Airline:
    United
    RT/OW
    Round Trip
    Number of Stops:
    No stops
    Date of Flight:
    August 2010
    Seat Class:
    economy

    I had nice flights both ways - both were on time taking off and landing, both comfortable, considerate staff, with no bumps!

    1. Flight Rating

    2. Check-in Experience:

    3. In-flight Service:

    4. Seat Comfort:

    “I'm crazy for BLUE”

    by taralj on July 10, 2010

    Flight from Boston to Chicago

    Airline:
    JetBlue
    RT/OW
    Round Trip
    Number of Stops:
    No stops
    Date of Flight:
    April 2010
    Seat Class:
    economy

    The flight from Boston to Chicago was nothing but great. The flight attendants were pleasant and always there to help. On my way back to Boston I wasn't crazy about the check in lady when trying to retrieve my tickets. Other than her it was fine.

    1. Flight Rating

    2. Check-in Experience:

    3. In-flight Service:

    4. Seat Comfort:

    “Love the 2 check-in bags but don't like the checkin”

    by raj12 on April 16, 2010

    Flight from Boston to Chicago

    Airline:
    Southwest
    Number of Stops:
    No stops
    Date of Flight:
    April 2010
    Seat Class:
    economy

    I got a great deal on Southwest for the fare and like the 2 checkin bags. I don't like the extra money on the priority check in...

    1. Flight Rating

    2. Check-in Experience:

    3. In-flight Service:

    4. Seat Comfort:

    “Love the DirectTV and the Free bag”

    by raj12 on April 14, 2010

    Flight from Boston to Chicago

    Airline:
    JetBlue
    Number of Stops:
    No stops
    Date of Flight:
    March 2010
    Seat Class:
    economy

    Loved the great seat (thanks to SeatGuru.com) and DirectTV for the flight. I was traveling with a heavy bag that I could check-in for free and not pay for it. The flight arrived early and all in all Loved the flight!

Flown this route before? Write a review
Sample Fares found by other travelers within the past 72 hours
Price From/To Depart/Return Airline
$196 Flight from Boston to O'Hare (BOS-ORD) Thu, May 23 - Sat, May 25 American Airlines
$196 Flight from Boston to O'Hare (BOS-ORD) Wed, May 22 - Sat, May 25 American Airlines
$196 Flight from Boston to O'Hare (BOS-ORD) Wed, May 22 - Wed, May 29 American Airlines
$236 Flight from Boston to O'Hare (BOS-ORD) Wed, May 22 - Fri, Jun 28 American Airlines
$250 Flight from Boston to O'Hare (BOS-ORD) Wed, May 22 - Tue, May 28 American Airlines
$281 Flight from Boston to O'Hare (BOS-ORD) Wed, May 22 - Fri, May 24 Delta Air Lines
$281 Flight from Boston to O'Hare (BOS-ORD) Thu, May 23 - Fri, May 24 Delta Air Lines
$281 Flight from Boston to O'Hare (BOS-ORD) Thu, May 23 - Thu, May 23 Delta Air Lines
$290 Flight from Boston to O'Hare (BOS-ORD) Mon, May 20 - Wed, May 22 American Airlines
$349 Flight from Boston to O'Hare (BOS-ORD) Thu, May 23 - Thu, May 23 American Airlines
There are approximately 872 flights covering the route from Logan International Airport in Boston to O'Hare International Airport in Chicago, provided by as many as 9 airlines.

The following airlines sometimes offer nonstop cheap flights from Boston to Chicago:

Transwest Air

As an alternative to flying from Boston, you may also want to try searching for cheap flights from Worcester (ORH).
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