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

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Fares from Chicago, IL (MDW)
$192 RT to
Boston, MA (BOS)
Sorry this deal is over or has been sold out! But here’s another great Airfarewatchdog verified fare for this route!
$192 RT Chicago to Boston, MA
Airline(s)
Southwest
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
Travel Ending:
Friday, 31 October 2014
More Details:
Non-Stop Flights, No min. stay, Fare can be bought one-way for half the lowest roundtrip price
Last Updated:
Saturday, 19 April 2014
Our Notes:
This is a fare from Southwest - visit Southwest.com to find this fare. Other airlines often match Southwest sales, so search other sites to find the best option.
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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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Check out these top-rated hotels in Boston
As rated by TripAdvisor® travelers
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"Convenience with Comfort" 04/17/2014
"Fabulous, even for one night!" 04/16/2014
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"Modern and well located" 04/18/2014
"Had a blast in Boston!" 04/16/2014
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"Boston's Best" 04/17/2014
"Top Notch All around!!!! Best Of Boston" 04/15/2014

More Flights From Chicago To Boston (MDW-BOS)

Price
Details
$214 RT No min. stay (AirTran, Delta) See all details »
  • Airline(s):
    AirTran, Delta
  • Seats are:
    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.
  • Advance Purchase:
    21 Days
  • Available for travel:
    7 Days/week, If Available
  • Travel ending:
    Friday, October 31, 2014
  • More Details:
    No Min. Stay
  • Last Updated:
    Saturday, April 19, 2014
  • Our Notes:
    CheapAir.com Will Include A Booking Fee Of $9.95.

Reviews for Chicago to Boston (MDW-BOS)

based on 1 reviews
Flown this route before? Write a review
    1. Flight Rating

    2. Check-in Experience:

    3. In-flight Service:

    4. Seat Comfort:

    Southwest continues to offer excellent basic service on time and without hidden charges - all leavened with a bit of humor. Too bad they are no longer the price leader on some routes.

    by Dreedassoc on July 16, 2010

    Flight from Chicago to Boston

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

    They continue to perform what an airline needs to do and have brought down prices wherever they fly. I don't always take them, but they are the first place I check.

Flown this route before? Write a review
Sample Fares found by other travelers within the past 72 hours
Price From/To Depart/Return Airline
$284 Flight from Midway to Boston (MDW-BOS) Fri, May 9 - Sun, May 11 Delta Air Lines
$284 Flight from Midway to Boston (MDW-BOS) Thu, May 15 - Sun, May 18 Delta Air Lines
$288 Flight from Midway to Boston (MDW-BOS) Sun, Apr 20 - Thu, Apr 24 Delta Air Lines
$324 Flight from Midway to Boston (MDW-BOS) Sat, May 10 - Sat, May 10 Delta Air Lines
$353 Flight from Midway to Boston (MDW-BOS) Mon, Apr 28 - Thu, May 1 Delta Air Lines
$353 Flight from Midway to Boston (MDW-BOS) Mon, Apr 28 - Wed, Apr 30 Delta Air Lines
$433 Flight from Midway to Boston (MDW-BOS) Thu, Apr 24 - Mon, Apr 28 Delta Air Lines
$473 Flight from Midway to Boston (MDW-BOS) Fri, Apr 25 - Sun, Apr 27 Delta Air Lines
$498 Flight from Midway to Boston (MDW-BOS) Sun, Apr 20 - Wed, Apr 23 Delta Air Lines
$720 Flight from Midway to Boston (MDW-BOS) Sat, Apr 26 - Mon, Apr 28 Delta Air Lines
There are approximately 26 flights covering the route from Midway Airport in Chicago to Logan International Airport in Boston, provided by as many as 2 airlines.

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

Transwest Air

As an alternative to flying from Chicago, you may also want to try searching for cheap flights from Chicago (ORD).
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