Home >> Fares From A City >> Chicago, IL >> Chicago, IL (MDW) To Boston, MA (BOS)
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HOW TO FIND THIS FARE
  • AIRLINES
    Southwest
  • ADVANCE PURCHASE REQUIRED
    21 DAYS BEFORE TRAVEL
  • DAYS AVAILABLE FOR TRAVEL
    Tue/Wed/Sat
  • TRAVEL ENDING
    Mon, March 07, 2016
Megan M.
Staff Airfare Analyst
Megan's Notes:
No min. stay. Fare can be bought one-way for half the lowest roundtrip price. Non-Stop 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 Chicago to Boston
1 Traveler Reviews
"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."
Flight from Chicago to Boston
Airline: Southwest
RT/OW: roundtrip
Date of Flight: July 2010
Seat Class: economy
Check-in Experience
In-flight Service
Seat Comfort
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.
Found by other travelers: Chicago, IL (MDW) to Boston, MA (BOS)
$565
Flight from Chicago to Boston (MDW - BOS)
Fri, Jun 20 - Tue, Jun 24
Delta
$237
Flight from Chicago to Boston (MDW - BOS)
Fri, Oct 24 - Mon, Oct 27
Delta
$358
Flight from Chicago to Boston (MDW - BOS)
Thu, Aug 7 - Thu, Aug 14
Delta
$237
Flight from Chicago to Boston (MDW - BOS)
Fri, Sep 26 - Mon, Sep 29
Delta
$373
Flight from Chicago to Boston (MDW - BOS)
Thu, Aug 14 - Mon, Aug 18
Delta
$430
Flight from Chicago to Boston (MDW - BOS)
Tue, Jun 24 - Mon, Jun 30
Delta
$302
Flight from Chicago to Boston (MDW - BOS)
Fri, Jun 6 - Mon, Jun 9
Delta
$481
Flight from Chicago to Boston (MDW - BOS)
Thu, Jul 24 - Sun, Jul 27
Delta
$568
Flight from Chicago to Boston (MDW - BOS)
Thu, Jul 24 - Mon, Jul 28
Delta
$456
Flight from Chicago to Boston (MDW - BOS)
Wed, Jul 23 - Sun, Jul 27
Delta
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 often offer cheap flights from Chicago to Boston
Southwest
Delta
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