Home >> Fares From A City >> Oakland, CA >> Oakland, CA (OAK) 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 ENDING
    Tue, March 08, 2016
Giuliana M.
Staff Airfare Analyst
Giuliana's Notes:
No min. stay. No peak summer travel at this price. Fare can be bought one-way for half the lowest roundtrip price. No peak holiday travel at this 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 Oakland to Chicago
2 Traveler Reviews
"Efficient and worth the price"
Flight from Oakland to Chicago
Airline: Southwest
RT/OW: roundtrip
Date of Flight: June 2011
Seat Class: economy
Check-in Experience
In-flight Service
Seat Comfort
Southwest is a great airline. They don't charge for bags (up to 2) and you want to reschedule or miss your flight, no big deal. I flew Alaska and Delta in April and it was a nightmare trying to change a ticket. I ended up forfeiting my second leg and buying a whole-new one-way ticket. The flight attendants are courteous and the seats are comfortable. It's a smart airline. I wish they flew into Bozeman, Montana. They would clean up.
Found by other travelers: Oakland, CA (OAK) to Chicago, IL (MDW)
$759
Flight from Oakland to Chicago (OAK - MDW)
Mon, Jun 9 - Wed, Jun 11
Delta
$637
Flight from Oakland to Chicago (OAK - MDW)
Thu, Jul 31 - Tue, Aug 5
Delta
$832
Flight from Oakland to Chicago (OAK - MDW)
Sun, Jun 15 - Mon, Jun 30
AirTran
$489
Flight from Oakland to Chicago (OAK - MDW)
Thu, Oct 9 - Mon, Oct 13
Delta
$612
Flight from Oakland to Chicago (OAK - MDW)
Mon, Jun 9 - Tue, Jun 17
Delta
$724
Flight from Oakland to Chicago (OAK - MDW)
Fri, Jul 18 - Sun, Jul 20
Delta
$530
Flight from Oakland to Chicago (OAK - MDW)
Sun, Jun 8 - Tue, Jun 17
Delta
$705
Flight from Oakland to Chicago (OAK - MDW)
Fri, Jul 25 - Sat, Aug 2
Delta
$466
Flight from Oakland to Chicago (OAK - MDW)
Mon, Oct 6 - Mon, Oct 13
Delta
$510
Flight from Oakland to Chicago (OAK - MDW)
Sat, Aug 30 - Mon, Sep 1
Delta
There are approximately 35 flights covering the route from Metropolitan Oakland International Airport in Oakland to Midway Airport in Chicago, provided by as many as 5 airlines.
The following airlines often offer cheap flights from Oakland to Chicago
Continental
Southwest
United
Frontier
US Airways
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