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Cheap Flights From Boston, Massachusetts (BOS) To Chicago, Illinois (CHI) - No Deals

Flight from Boston to Chicago (BOS-MDW)

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Reviews for Boston to Chicago (BOS-MDW)

based on 2 reviews
Flown this route before? Write a review
    1. Flight Rating

    2. Check-in Experience:

    3. In-flight Service:

    4. Seat Comfort:

    Excellent

    by Phealy on March 31, 2011

    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!!

    1. Flight Rating

    2. Check-in Experience:

    3. In-flight Service:

    4. Seat Comfort:

    Southwest does good when flying to Chicago

    by iflysometimes on April 12, 2010

    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!

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Sample Fares found by other travelers within the past 72 hours
Price From/To Depart/Return Airline
$365 Flight from Boston to Midway (BOS-MDW) Sat, Jun 7 - Sun, Jun 8 Delta Air Lines
$405 Flight from Boston to Midway (BOS-MDW) Thu, Jun 5 - Fri, Jun 6 Delta Air Lines
$415 Flight from Boston to Midway (BOS-MDW) Fri, Jun 6 - Sun, Jun 8 Delta Air Lines
$455 Flight from Boston to Midway (BOS-MDW) Fri, Jun 6 - Sun, Jun 8 Delta Air Lines
$508 Flight from Boston to Midway (BOS-MDW) Tue, Jun 10 - Thu, Jun 12 Delta Air Lines
$518 Flight from Boston to Midway (BOS-MDW) Mon, Jun 9 - Thu, Jun 12 Delta Air Lines
$518 Flight from Boston to Midway (BOS-MDW) Sat, Jun 7 - Mon, Jun 9 Delta Air Lines
$518 Flight from Boston to Midway (BOS-MDW) Mon, Jun 9 - Wed, Jun 11 Delta Air Lines
$800 Flight from Boston to Midway (BOS-MDW) Sat, Jun 7 - Sat, Jun 14 Delta Air Lines
$844 Flight from Boston to Midway (BOS-MDW) Wed, Jun 11 - Thu, Jun 19 Delta Air Lines
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 sometimes offer nonstop cheap flights from Boston to Chicago:

Transwest Air

As an alternative to flying from Boston, you may also want to try searching for cheap flights from Worcester (ORH).
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