Home >> Fares From A City >> San Diego, CA >> San Diego, CA (SAN) To Chicago, IL (MDW)
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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 STARTING
    Tue, August 23, 2016
  • TRAVEL ENDING
    Wed, November 02, 2016
Peter T.
Staff Airfare Analyst
Peter's Notes:
Non-stop.
Certain travel dates only! No min. stay. Fare can be bought one-way for half the lowest roundtrip price. Late Summer/Fall travel.
Travel between late August and early November.

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 San Diego to Chicago
2 Traveler Reviews
"Great ride!"
Flight from San Diego to Chicago
Airline: Southwest
RT/OW: roundtrip
Date of Flight: November 2010
Seat Class: economy
Check-in Experience
In-flight Service
Seat Comfort
What a thrill, everyone piled into little worn out seats for 5 hours of nonstop flight. It reminds me of the rural buses in Mexico, all you need are the live chickens! But what am I doing? Basically I am selling my time for $40 per hour each way as the next competing flight would have cost me $400 more, so bring on the chickens! They are safe, reliable, and more than courteous. Go Southwest!!!!! I luv them!
Found by other travelers: San Diego, CA (SAN) to Chicago, IL (MDW)
$320
Flight from to Chicago (SAN - MDW)
Thu, Sep 4 - Tue, Sep 9
Delta
$616
Flight from to Chicago (SAN - MDW)
Wed, Jun 25 - Tue, Jul 1
Frontier
$582
Flight from to Chicago (SAN - MDW)
Thu, Jun 26 - Wed, Jul 2
Delta
$485
Flight from to Chicago (SAN - MDW)
Tue, Jun 24 - Wed, Jul 2
Delta
$542
Flight from to Chicago (SAN - MDW)
Fri, Jun 6 - Tue, Jun 10
Delta
$541
Flight from to Chicago (SAN - MDW)
Thu, Jul 3 - Sat, Jul 5
Delta
$554
Flight from to Chicago (SAN - MDW)
Thu, Jun 19 - Fri, Jun 20
Delta
$429
Flight from to Chicago (SAN - MDW)
Tue, Dec 23 - Wed, Dec 24
Delta
$484
Flight from to Chicago (SAN - MDW)
Thu, Jul 3 - Fri, Jul 11
Delta
$320
Flight from to Chicago (SAN - MDW)
Sat, Sep 20 - Wed, Sep 24
AirTran
There are approximately 38 flights covering the route from San Diego International Airport in to Midway Airport in Chicago, provided by as many as 6 airlines.
The following airlines often offer cheap flights from to Chicago
Continental
Southwest
United
Frontier
Delta
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