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Cheap Flights From Boston, Massachusetts (BOS) To Chicago, Illinois (MDW)

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Fares from Boston, MA (BOS)
$184 RT 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!
$184 RT Boston to Chicago, IL
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Airline(s)
Delta
Seats:
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.
Adv. Purchase:
7 Days
Available:
Mon-Sat
Travel Ending:
Friday, 05 June 2015
More Details:
No peak holiday travel at this price
Last Updated:
Monday, 24 November 2014
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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 Flights From Boston To Chicago (BOS-MDW)

Price
Details
$184 RT Lowest fare found for travel within the next 30 days. (Delta) See all details »
  • Airline(s):
    Delta
  • Seats are:
    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.
  • Advance Purchase:
    20 Days
  • Available for travel:
    Mon-Wed & Sun
  • Travel starting:
    Sunday, 14 December 2014
  • More Details:
    Lowest Fare Found For Travel Within The Next 30 Days.
  • Last Updated:
    Monday, November 24, 2014
$162 RT Non-Stop Flights. No min. stay. Fare can be bought one-way for half the... (Southwest) See all details »
  • Airline(s):
    Southwest
  • Seats are:
    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.
  • Advance Purchase:
    21 Days
  • Available for travel:
    Tue/Wed/Sat
  • Travel ending:
    Friday, June 5, 2015
  • More Details:
    Non-Stop Flights, No Min. Stay, Fare Can Be Bought One-way For Half The Lowest Roundtrip Price, No Peak Holiday Travel At This Price
  • Last Updated:
    Monday, November 24, 2014
  • Our Notes:
    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 ...morethe best option.

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!

Flown this route before? Write a review
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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