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Cheap Flights From Boston, Massachusetts To Chicago, Illinois
Boston
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Airfare Details for flights from Boston to Chicago
Search Now for Low Fares
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Airline(s):Southwest
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Seats are:Limited Availability
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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
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Last Updated:Tuesday, June 18, 2013
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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. 
Are Your Travel Dates Set? Check Fares Now:
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More Flights From Boston To Chicago (BOS-MDW)
Price
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Details
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|---|---|
| $240 RT | Non-Stop Flights. No min. stay. Fare can be bought one-way for half the... (Southwest) See all details » |
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| $240 RT | No min. stay. Travel between Aug. 26 - Dec. 18, 2013 (Delta, AirTran) See all details » |
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Reviews for Boston to Chicago (BOS-MDW)
Flown this route before? Write a review
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Flight from Boston to Chicago
- Airline:
- Southwest
- RT/OW
- Round Trip
- Number of Stops:
- No stops
- Date of Flight:
- March 2011
- Seat Class:
- economy
I fly this trip almost evry weekend for the past two years. Southwest allows me to work in boston and spend my weekends outside of Chicago. 98% of the time we are on time, or early. Southwest is efficent, friendly, economical and a pleasure to fly. I fly enough so I get priority boarding, which I must say is great. Not sure i would be happy getting a high B number and being stuck in a middle seat. Otherwise, hats off to southwest!!
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“Southwest does good when flying to Chicago”
Flight from Boston to Chicago
- Airline:
- Southwest
- Number of Stops:
- No stops
- Date of Flight:
- November 2009
- Seat Class:
- economy
Overall, the flights to Chicago from Boston and back were nice. Gates were clean with plenty of room for everyone with ample access to food. I'm not typically a big fan of the bulk boarding concept, but the SW team kept us moving and it actually made the process smoother than when I have an assigned seat on other airlines. You better be in the top 20 of the B group if you and your companion want to sure fire way to sit together. Check-in online 24 ahead of time!
Flown this route before? Write a review
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