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Cheap Flights From Oakland, California To Chicago, Illinois
Oakland
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Airfare Details for flights from Oakland to Chicago

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Sorry this deal is over or has been sold out! But here’s another great Airfarewatchdog verified fare for this route!

$326 RT flight from Oakland to Chicago (OAK-MDW)

  • Airline(s):
    Southwest
  • Seats are:
    Limited Availability
  • More Details:
    Non-Stop Flights, No Min. Stay, Fare Can Be Bought One-way For Half The Lowest Roundtrip Price, Travel Between Aug. 26 - Dec. 18, 2013
  • Last Updated:
    Tuesday, June 18, 2013
  • Our Notes:
    Blackout dates apply: Sept. 2 and Nov. 26 - Dec. 3. Fare only available on Southwest.com Do not use the fare calendar below to find seats at this fare. ...moreOnly use the Southwest link shown.
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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Reviews

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
$533 Flight from Oakland to Midway (OAK-MDW) Tue, Jul 9 - Thu, Jul 18 Delta Air Lines
$534 Flight from Oakland to Midway (OAK-MDW) Mon, Jun 24 - Tue, Jun 25 Delta Air Lines
$595 Flight from Oakland to Midway (OAK-MDW) Tue, Jul 2 - Sat, Jul 6 Delta Air Lines
$669 Flight from Oakland to Midway (OAK-MDW) Fri, Jun 28 - Sun, Jun 30 Delta Air Lines
$679 Flight from Oakland to Midway (OAK-MDW) Wed, Jul 10 - Sun, Jul 14 Delta Air Lines
$702 Flight from Oakland to Midway (OAK-MDW) Mon, Jun 24 - Fri, Jun 28 Delta Air Lines
$771 Flight from Oakland to Midway (OAK-MDW) Thu, Jul 11 - Sun, Jul 14 Delta Air Lines
$773 Flight from Oakland to Midway (OAK-MDW) Thu, Jul 4 - Mon, Jul 8 Delta Air Lines
$898 Flight from Oakland to Midway (OAK-MDW) Thu, Jul 4 - Sun, Jul 7 Delta Air Lines
$1,024 Flight from Oakland to Midway (OAK-MDW) Sun, Jun 23 - Sun, Jun 23 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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