Airfarewatchdog

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

Search Now for Low Fares
 
Find Flights
Fares from Boston, MA (BOS)
$192 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!
$192 RT Boston to Chicago, IL
Airline(s)
Southwest
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:
21 Days
Travel Ending:
Friday, 31 October 2014
More Details:
Non-Stop Flights, No min. stay, Fare can be bought one-way for half the lowest roundtrip price
Last Updated:
Wednesday, 23 April 2014
Our Notes:
This is a fare from Southwest - visit Southwest.com to find this fare. Other airlines often match Southwest sales, so search other sites to find the best option.
Sign up for alerts on this route:
Please provide an e-mail address.

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.

Find a flight for your dates:
 
Find Flights
Check out these top-rated hotels in Chicago
As rated by TripAdvisor® travelers
Enter dates & see best prices*
Enter your travel dates to see the best prices*
We're sorry, we can't find availability for your dates. Try changing your travel dates to see the best prices*
 
"Might Try Again" 04/22/2014
"Great weekend!!!" 04/22/2014
Enter dates & see best prices*
Enter your travel dates to see the best prices*
We're sorry, we can't find availability for your dates. Try changing your travel dates to see the best prices*
 
"Amazing hotel and excellent staff!" 04/22/2014
"Perfect - AGAIN !!!" 04/21/2014
Enter dates & see best prices*
Enter your travel dates to see the best prices*
We're sorry, we can't find availability for your dates. Try changing your travel dates to see the best prices*
 
"A Home Run of a Weekend" 03/11/2014
"Excellent service, great value" 03/07/2014

More Flights From Boston To Chicago (BOS-MDW)

Price
Details
$214 RT No min. stay (AirTran, Delta) See all details »
  • Airline(s):
    AirTran, 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:
    21 Days
  • Travel ending:
    Friday, October 31, 2014
  • More Details:
    No Min. Stay
  • Last Updated:
    Wednesday, April 23, 2014
  • Our Notes:
    CheapAir.com Will Include A Booking Fee Of $9.95.

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
$262 Flight from Boston to Midway (BOS-MDW) Tue, May 6 - Fri, May 9 Delta Air Lines
$262 Flight from Boston to Midway (BOS-MDW) Mon, May 5 - Tue, May 6 Delta Air Lines
$288 Flight from Boston to Midway (BOS-MDW) Tue, Apr 29 - Wed, Apr 30 Delta Air Lines
$353 Flight from Boston to Midway (BOS-MDW) Sun, Apr 27 - Wed, Apr 30 Delta Air Lines
$433 Flight from Boston to Midway (BOS-MDW) Sat, May 3 - Sun, May 4 Delta Air Lines
$497 Flight from Boston to Midway (BOS-MDW) Fri, May 2 - Tue, May 6 Delta Air Lines
$589 Flight from Boston to Midway (BOS-MDW) Fri, May 2 - Tue, May 6 Delta Air Lines
$694 Flight from Boston to Midway (BOS-MDW) Fri, May 2 - Sun, May 4 Delta Air Lines
$720 Flight from Boston to Midway (BOS-MDW) Fri, Apr 25 - Sun, Apr 27 Delta Air Lines
$771 Flight from Boston to Midway (BOS-MDW) Fri, Apr 25 - Sun, Apr 27 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).
Advertisement
Advertisement
Advertisement
http://rd.airfarewatchdog.com/?ad_user_tracking=%5Bsource%3D%2Ctaparam%3D%2Csupmt%3D%5D