Please confirm your Email address
Welcome!
Cheap Flights From Boston, Massachusetts To Chicago, Illinois
Boston
- Real deals from your departure city
- Verified by our Dealhounds
Popular Destinations
- Cheap flights to Amsterdam
- Cheap flights to Beijing
- Cheap flights to Brussels
- Cheap flights to Cancun
- Cheap flights to Chicago
- Cheap flights to Cozumel
- Cheap flights to Denver
- Cheap flights to Frankfurt
- Cheap flights to Ft. Lauderdale
- Cheap flights to Honolulu
- Cheap flights to Las Vegas
- Cheap flights to London
- Cheap flights to Los Angeles
- Cheap flights to Los Cabos
- Cheap flights to Mexico City
Popular Routes
- Cheap flights from Seattle to Boston
- Cheap flights from Washington, D.C. to Chicago
- Cheap flights from Jacksonville to Chicago
- Cheap flights from Denver to Los Angeles
- Cheap flights from Syracuse to Atlanta
- Cheap flights from Allentown to Orlando
- Cheap flights from Los Angeles to Milwaukee
- Cheap flights from New York City to Charlotte
- Cheap flights from Orlando to White Plains
- Cheap flights from Washington, D.C. to Honolulu
Airfare Details for flights from Boston to Chicago
Search Now for Low Fares
-
Airline(s):Southwest
-
Seats are:Limited Availability
-
Advance Purchase:7 Days
-
Available for travel:Tue/Wed
-
Travel by:Sunday, January 5, 2014
-
More Details:Nonstop Incl. All Taxes, No Min. Stay, Fare Can Be Bought One-way For Half The Lowest Roundtrip Price
-
Last Updated:Friday, May 17, 2013
-
Our Notes:Southwest Fares Can Only Be Booked On Southwest.com. Other Airlines Often Match Each Other On Sale Fares.
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:
Check out these top-rated hotels in Chicago
As rated by TripAdvisor® travelers
Show the lowest price for this hotel*
*from our partners
"First visit better than we'd dreamed of"
05/13/2013
"Best hotel experience"
05/12/2013
Show the lowest price for this hotel*
*from our partners
Show the lowest price for this hotel*
*from our partners
More Flights From Boston To Chicago (BOS-MDW)
Price
|
Details
|
|---|---|
| $224 RT | Includes all taxes. No min. stay. Fare can be bought one-way for half t... (AirTran) See all details » |
| |
Reviews for Boston to Chicago (BOS-MDW)
Flown this route before? Write a review
-
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!!
-
“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
Advertisement
Advertisement
See What Our Dealhounds Have Found from Other Cities
Advertisement
© 1998-2013 Smarter Travel Media LLC. All Rights Reserved Privacy Statement | Terms of Use
Advertisement
