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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!

$218 RT flight from Boston to Chicago (BOS-ORD)

  • Airline(s):
    American, JetBlue, United
  • Seats are:
    Limited Availability
  • Travel by:
    Wednesday, December 18, 2013
  • More Details:
    Non-Stop Flights, No Min. Stay, Travel Between Aug. 26 - Dec. 18, 2013
  • Last Updated:
    Wednesday, June 19, 2013
  • Our Notes:
    We Found Travel Departing Sep 19 And Returning Sep 26.
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.

Buy This Fare Direct

Dealhound Confirmed! Find Fare Now On:

For best results, search by flexible dates.
CheapAir.com Hotwire (December) Hotwire (November) Hotwire (October) Hotwire (September) Hotwire_(Aug-Sep)

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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
$372 Flight from Boston to O'Hare (BOS-ORD) Thu, Jun 20 - Wed, Jun 26 Delta Air Lines
$382 Flight from Boston to O'Hare (BOS-ORD) Thu, Jun 20 - Fri, Jun 21 Delta Air Lines
$402 Flight from Boston to O'Hare (BOS-ORD) Thu, Jun 20 - Fri, Jun 28 Delta Air Lines
$421 Flight from Boston to O'Hare (BOS-ORD) Thu, Jun 20 - Fri, Jun 28 Delta Air Lines
$421 Flight from Boston to O'Hare (BOS-ORD) Thu, Jun 20 - Fri, Jun 28 American Airlines
$431 Flight from Boston to O'Hare (BOS-ORD) Thu, Jun 20 - Mon, Jun 24 Delta Air Lines
$431 Flight from Boston to O'Hare (BOS-ORD) Thu, Jun 20 - Mon, Jun 24 American Airlines
$432 Flight from Boston to O'Hare (BOS-ORD) Thu, Jun 20 - Fri, Jun 28 Delta Air Lines
$437 Flight from Boston to O'Hare (BOS-ORD) Thu, Jun 20 - Sun, Jun 23 Delta Air Lines
$441 Flight from Boston to O'Hare (BOS-ORD) Thu, Jun 20 - Fri, Jun 28 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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