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

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Fares from Chicago, IL (MDW)
$216 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!
$216 RT Chicago to Boston, MA
Airline(s)
AirTran, Delta
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:
Wednesday, 31 December 2014
More Details:
No min. stay
Last Updated:
Wednesday, 30 July 2014
Our Notes:
CheapAir charges a $9.95 booking fee.
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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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More Flights From Chicago To Boston (MDW-BOS)

Price
Details
$216 RT Lowest fare found for travel within the next 30 days. (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:
    20 Days
  • Available for travel:
    Tue-Wed
  • Travel starting:
    Tuesday, 19 August 2014
  • More Details:
    Lowest Fare Found For Travel Within The Next 30 Days.
  • Last Updated:
    Wednesday, July 30, 2014
$200 RT Non-Stop Flights. No min. stay. Fare can be bought one-way for half the... (Southwest) See all details »
  • Airline(s):
    Southwest
  • 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:
    Thursday, January 1, 2015
  • More Details:
    Non-Stop Flights, No Min. Stay, Fare Can Be Bought One-way For Half The Lowest Roundtrip Price
  • Last Updated:
    Wednesday, July 30, 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 ...moreoption.
$228 RT No min. stay. Fare can be bought one-way for half the lowest roundtrip ... (Southwest) See all details »
  • Airline(s):
    Southwest
  • 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.
  • Available for travel:
    Mon-Thur & Sat
  • Travel starting:
    Monday, 25 August 2014
  • Travel ending:
    Wednesday, December 17, 2014
  • More Details:
    No Min. Stay, Fare Can Be Bought One-way For Half The Lowest Roundtrip Price, Fall/Winter Travel
  • Last Updated:
    Tuesday, July 22, 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 ...moreoption. Blackout Dates Apply: November 25 - 26 and November 29 - December 1, 2014.

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
$292 Flight from Midway to Boston (MDW-BOS) Thu, Jun 5 - Fri, Jun 6 Delta Air Lines
$302 Flight from Midway to Boston (MDW-BOS) Fri, Jun 6 - Mon, Jun 9 Delta Air Lines
$355 Flight from Midway to Boston (MDW-BOS) Tue, Jun 10 - Fri, Jun 13 Delta Air Lines
$405 Flight from Midway to Boston (MDW-BOS) Thu, Jun 5 - Mon, Jun 9 Delta Air Lines
$405 Flight from Midway to Boston (MDW-BOS) Fri, Jun 6 - Sat, Jun 7 Delta Air Lines
$415 Flight from Midway to Boston (MDW-BOS) Fri, Jun 6 - Sun, Jun 8 Delta Air Lines
$443 Flight from Midway to Boston (MDW-BOS) Wed, Jun 11 - Sat, Jun 14 Delta Air Lines
$468 Flight from Midway to Boston (MDW-BOS) Wed, Jun 11 - Fri, Jun 13 Delta Air Lines
$513 Flight from Midway to Boston (MDW-BOS) Wed, Jun 11 - Wed, Jun 25 Delta Air Lines
$518 Flight from Midway to Boston (MDW-BOS) Fri, Jun 6 - Tue, Jun 10 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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