Home >> Fares From A City >> Boston, MA >> Boston, MA (BOS) To Chicago, IL (MDW)
Sorry this deal is over or has been sold out.
But here's another great Airfarewatchdog
verified fare for this route!
Watch this route: get alerts when prices drop
Enter Your Email to Get Alerts.
Congratulations!
You'll now receive email alerts on fares from Boston, MA (BOS) to Chicago, IL (MDW)
HOW TO FIND THIS FARE
  • AIRLINES
    Southwest
  • DAYS AVAILABLE FOR TRAVEL
    Tue/Wed
  • TRAVEL STARTING
    Tue, September 15, 2015
  • TRAVEL ENDING
    Wed, November 11, 2015
Megan M.
Staff Airfare Analyst
Megan's Notes:
Certain travel dates only! No min. stay. Fare can be bought one-way for half the lowest roundtrip price. Fall travel; Nonstop flights.

This is a fare from Southwest, please visit Southwest.com to find this fare. Other airlines often match Southwest sales, so search other sites to find the best option.

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.

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.

More Details
Close Details
Reviews for Boston to Chicago
2 Traveler Reviews
"Excellent"
Flight from Boston to Chicago
Airline: Southwest
RT/OW: roundtrip
Date of Flight: March 2011
Seat Class: economy
Check-in Experience
In-flight Service
Seat Comfort
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!!
Found by other travelers: Boston, MA (BOS) to Chicago, IL (MDW)
$844
Flight from Boston to Chicago (BOS - MDW)
Wed, Jun 11 - Thu, Jun 19
Delta
$542
Flight from Boston to Chicago (BOS - MDW)
Thu, Jul 17 - Sat, Jul 19
Delta
$220
Flight from Boston to Chicago (BOS - MDW)
Tue, Oct 21 - Sat, Oct 25
Delta
$451
Flight from Boston to Chicago (BOS - MDW)
Fri, Jul 4 - Mon, Jul 7
Delta
$364
Flight from Boston to Chicago (BOS - MDW)
Thu, Oct 9 - Sun, Oct 12
Delta
$800
Flight from Boston to Chicago (BOS - MDW)
Sat, Jun 7 - Sat, Jun 14
Delta
$460
Flight from Boston to Chicago (BOS - MDW)
Thu, Jul 3 - Sun, Jul 6
Delta
$626
Flight from Boston to Chicago (BOS - MDW)
Fri, Jun 20 - Sun, Jun 22
Delta
$475
Flight from Boston to Chicago (BOS - MDW)
Fri, Jul 4 - Sun, Jul 13
Delta
$401
Flight from Boston to Chicago (BOS - MDW)
Tue, Jul 15 - Thu, Jul 17
Delta
There are approximately 20 flights covering the route from Logan International Airport in Boston to Midway Airport in Chicago, provided by as many as 2 airlines.
The following airlines often offer cheap flights from Boston to Chicago
Southwest
Delta
Don't Miss the Lowest Fares!
We'll alert you when prices drop!
First name is a required field
Enter valid email address
Departure city is a required field
Thanks and Welcome!
Your first Fare Alert will appear before you know it.
Click here to add more departure cities
Find Out First About Low Fares!
First Name:
First name is a required field
Email Address:
Enter valid email address
Thanks for signing up!
You'll hear from our Dealhounds as soon as we find new low fares from:
to
Your Travel Dates: to
We did the hard Work!
We've analyzed hotels and found the best values.
See Our List!