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Cheap Flights From Boston, Massachusetts (BOS) To Chicago, Illinois (ORD)

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Fares from Boston, MA (BOS)
$186 RT to
Chicago, IL (ORD)
Sorry this deal is over or has been sold out! But here’s another great Airfarewatchdog verified fare for this route!
$186 RT Boston to Chicago, IL
Airline(s)
United, American, JetBlue
Seats:
Seats are not available on all flights or all dates of travel. You may need to have flexible travel dates to find this fare. Fares for travel on holidays may be higher.
Adv. Purchase:
21 Days
Available:
7 days/week, if available
More Details:
Year-round travel; Nonstop flights, No min. stay
Last Updated:
Wednesday, 16 April 2014
Our Notes:
We found seats for departure MAY 14 and return MAY 21. There are other dates available as well. JetBlue bookable through 1/5/2015. CheapAir.com will include a booking fee of $9.95.
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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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As rated by TripAdvisor® travelers
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"Great hotel" 04/16/2014
"Weekend Getaway" 04/15/2014
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"Not as Advertised" 04/15/2014
"Beautiful property, Amazing Service.....a must experience!!!" 04/14/2014
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"A Home Run of a Weekend" 03/11/2014
"Excellent service, great value" 03/07/2014

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
$282 Flight from Boston to O'Hare (BOS-ORD) Fri, Apr 18 - Sun, Apr 20 Delta Air Lines
$282 Flight from Boston to O'Hare (BOS-ORD) Wed, Apr 16 - Sun, Apr 20 US Airways
$282 Flight from Boston to O'Hare (BOS-ORD) Wed, Apr 16 - Sun, Apr 20 Delta Air Lines
$288 Flight from Boston to O'Hare (BOS-ORD) Fri, Apr 18 - Sat, Apr 19 Delta Air Lines
$288 Flight from Boston to O'Hare (BOS-ORD) Thu, Apr 17 - Sun, Apr 20 Delta Air Lines
$288 Flight from Boston to O'Hare (BOS-ORD) Thu, Apr 17 - Sat, Apr 19 Delta Air Lines
$393 Flight from Boston to O'Hare (BOS-ORD) Fri, Apr 18 - Sat, Apr 19 Delta Air Lines
$393 Flight from Boston to O'Hare (BOS-ORD) Fri, Apr 18 - Sat, Apr 19 Delta Air Lines
$393 Flight from Boston to O'Hare (BOS-ORD) Thu, Apr 17 - Sat, Apr 19 Delta Air Lines
$393 Flight from Boston to O'Hare (BOS-ORD) Thu, Apr 17 - Sun, Apr 20 Delta Air Lines
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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