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Cheap Flights From Oakland, California (OAK) To Chicago, Illinois (MDW)

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Fares from Oakland, CA (OAK)
$266 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!
$266 RT Oakland 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
Available:
7 days/week, if available
Travel Ending:
Monday, 06 April 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:
Tuesday, 02 September 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.
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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.

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More Flights From Oakland To Chicago (OAK-MDW)

Price
Details
$292 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:
    15 Days
  • Available for travel:
    Mon-Thur & Sat
  • Travel starting:
    Tuesday, 16 September 2014
  • More Details:
    Lowest Fare Found For Travel Within The Next 30 Days.
  • Last Updated:
    Tuesday, September 2, 2014

Reviews for Oakland to Chicago (OAK-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:

    Efficient and worth the price

    by oblio on July 7, 2011

    Flight from Oakland to Chicago

    Airline:
    Southwest
    RT/OW
    Round Trip
    Number of Stops:
    No stops
    Date of Flight:
    June 2011
    Seat Class:
    economy

    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.

    1. Flight Rating

    2. Check-in Experience:

    3. In-flight Service:

    4. Seat Comfort:

    Nothing new or different.....

    by judesbabe on July 22, 2010

    Flight from Oakland to Chicago

    Airline:
    Southwest
    RT/OW
    Round Trip
    Number of Stops:
    No stops
    Date of Flight:
    July 2010
    Seat Class:
    economy

    Flight was running late, but we still arrived close to our original arrival time. Nice staff, seats were just fine. It was a bit expensive for a nonstop flight, but worth it. No movies on Southwest, same ole snacks. Seats are pretty good. I would say this was a pretty average flight.

Flown this route before? Write a review
Sample Fares found by other travelers within the past 72 hours
Price From/To Depart/Return Airline
$530 Flight from Oakland to Midway (OAK-MDW) Sun, Jun 8 - Tue, Jun 17 Delta Air Lines
$612 Flight from Oakland to Midway (OAK-MDW) Mon, Jun 9 - Tue, Jun 17 Delta Air Lines
$635 Flight from Oakland to Midway (OAK-MDW) Sat, Jun 14 - Wed, Jun 18 Delta Air Lines
$759 Flight from Oakland to Midway (OAK-MDW) Mon, Jun 9 - Wed, Jun 11 Delta Air Lines
$765 Flight from Oakland to Midway (OAK-MDW) Fri, Jun 13 - Tue, Jun 17 Delta Air Lines
$782 Flight from Oakland to Midway (OAK-MDW) Mon, Jun 9 - Mon, Jun 23 AirTran
$801 Flight from Oakland to Midway (OAK-MDW) Thu, Jun 12 - Tue, Jun 17 Delta Air Lines
$891 Flight from Oakland to Midway (OAK-MDW) Thu, Jun 12 - Sun, Jun 15 Delta Air Lines
$956 Flight from Oakland to Midway (OAK-MDW) Thu, Jun 12 - Sun, Jun 15 Delta Air Lines
$984 Flight from Oakland to Midway (OAK-MDW) Fri, Jun 13 - Sun, Jun 15 Delta Air Lines
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 sometimes offer nonstop cheap flights from Oakland to Chicago:

Transwest Air

As an alternative to flying from Oakland, you may also want to try searching for cheap flights from San Francisco (SFO).
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