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

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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 Chicago to Boston (MDW-BOS)

  • Airline(s):
    Southwest
  • Seats are:
    Limited Availability
  • Available for travel:
    Exc Fri/Sun
  • More Details:
    Non-Stop Flights, No Min. Stay, Fare Can Be Bought One-way For Half The Lowest Roundtrip Price, Travel Between Aug. 26 - Dec. 18, 2013
  • Last Updated:
    Tuesday, June 18, 2013
  • Our Notes:
    Blackout dates apply: Sept. 2 and Nov. 26 - Dec. 3. Fare only available on Southwest.com Do not use the fare calendar below to find seats at this fare. ...moreOnly use the Southwest link shown.
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
$240 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:
    Limited Availability
  • Advance Purchase:
    14 Days
  • Available for travel:
    7 Days/week If Available
  • Travel by:
    Sunday, January 5, 2014
  • More Details:
    Non-Stop Flights, No Min. Stay, Fare Can Be Bought One-way For Half The Lowest Roundtrip Price
  • Last Updated:
    Tuesday, June 18, 2013
  • Our Notes:
    Southwest fares can only be booked on Southwest.com. Other airlines often match each other on sale fares. Do not use the fare calendar below to find seats ...moreat this fare. Only use the Southwest link shown.
$240 RT No min. stay. Fare can be bought one-way for half the lowest roundtrip ... (AirTran) See all details »
  • Airline(s):
    AirTran
  • Seats are:
    Limited Availability
  • Available for travel:
    Exc Fri/Sun
  • Travel by:
    Wednesday, December 18, 2013
  • More Details:
    No Min. Stay, Fare Can Be Bought One-way For Half The Lowest Roundtrip Price, Travel Between Aug. 26 - Dec. 18, 2013
  • Last Updated:
    Tuesday, June 18, 2013
Reviews

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
$352 Flight from Midway to Boston (MDW-BOS) Fri, Jun 21 - Mon, Jul 1 Delta Air Lines
$352 Flight from Midway to Boston (MDW-BOS) Sun, Jun 23 - Sat, Jul 13 Delta Air Lines
$392 Flight from Midway to Boston (MDW-BOS) Sun, Jun 23 - Thu, Jun 27 Delta Air Lines
$402 Flight from Midway to Boston (MDW-BOS) Sat, Jun 22 - Sun, Jun 23 Delta Air Lines
$402 Flight from Midway to Boston (MDW-BOS) Mon, Jun 24 - Mon, Jun 24 Delta Air Lines
$402 Flight from Midway to Boston (MDW-BOS) Fri, Jun 21 - Mon, Jun 24 Delta Air Lines
$402 Flight from Midway to Boston (MDW-BOS) Thu, Jun 20 - Sun, Jun 23 Delta Air Lines
$402 Flight from Midway to Boston (MDW-BOS) Fri, Jun 21 - Sun, Jun 23 Delta Air Lines
$442 Flight from Midway to Boston (MDW-BOS) Thu, Jun 20 - Thu, Jun 20 Delta Air Lines
$442 Flight from Midway to Boston (MDW-BOS) Thu, Jun 20 - Sun, Jun 23 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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