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

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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!

$272 RT flight from Chicago to Oakland (MDW-OAK)

  • Airline(s):
    Southwest
  • Seats are:
    Limited Availability
  • Available for travel:
    Exc Fri/Sun
  • Travel by:
    Wednesday, December 18, 2013
  • More Details:
    Includes All Taxes, 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, May 21, 2013
  • Our Notes:
    Blackout Dates Apply: Nov. 26 - Dec. 3.Fare Available On Southwest.com
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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Check out these top-rated hotels in Oakland
As rated by TripAdvisor® travelers
Best Western Plus Bayside Hotel
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*from our partners
"Good place in Oakland" 05/21/2013
"The experience is soooooo good!!" 05/20/2013
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Executive Inn and Suites
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*from our partners
"Best East Bay Business Hotel" 05/19/2013
"a most positive hotel experience!" 05/14/2013
Read all 428 Reviews »
Holiday Inn Express Oakland
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*from our partners
"Not bad for a short stay." 05/14/2013
"Good Choice for Oakland Area" 05/07/2013
Read all 146 Reviews »
Reviews

Reviews for Chicago to Oakland (MDW-OAK)

based on 1 reviews
Flown this route before? Write a review

    1. Flight Rating

    2. Check-in Experience:

    3. In-flight Service:

    4. Seat Comfort:

    “Halloween in the Black hole”

    by bigfoot11 on January 6, 2011

    Flight from Chicago to Oakland

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

    Flight to Oakland, ca was pleasant on SWA. Fri. evening departure, with little in the way of weather, until landing @OAK. Nice landing, despite nasty Xwinds. Return, Mon..post Raider game, again uneventful. Just what was ordered after Halloween in the Black Hole! Now THAT was an experience!

Flown this route before? Write a review
Sample Fares found by other travelers within the past 72 hours
Price From/To Depart/Return Airline
$369 Flight from Midway to Oakland (MDW-OAK) Thu, Jun 6 - Mon, Jun 10 Delta Air Lines
$412 Flight from Midway to Oakland (MDW-OAK) Tue, Jun 4 - Sat, Jun 8 Delta Air Lines
$442 Flight from Midway to Oakland (MDW-OAK) Fri, May 31 - Sun, Jun 2 Delta Air Lines
$628 Flight from Midway to Oakland (MDW-OAK) Sun, May 26 - Tue, May 28 Delta Air Lines
$628 Flight from Midway to Oakland (MDW-OAK) Thu, May 23 - Fri, May 31 Delta Air Lines
$642 Flight from Midway to Oakland (MDW-OAK) Wed, May 22 - Fri, May 24 Delta Air Lines
$722 Flight from Midway to Oakland (MDW-OAK) Thu, May 23 - Mon, May 27 Delta Air Lines
$762 Flight from Midway to Oakland (MDW-OAK) Thu, May 23 - Mon, May 27 Delta Air Lines
$925 Flight from Midway to Oakland (MDW-OAK) Thu, May 23 - Mon, May 27 Delta Air Lines
$925 Flight from Midway to Oakland (MDW-OAK) Sun, May 26 - Mon, May 27 Delta Air Lines
There are approximately 33 flights covering the route from Midway Airport in Chicago to Metropolitan Oakland International Airport in Oakland, provided by as many as 5 airlines.

The following airlines sometimes offer nonstop cheap flights from Chicago to Oakland:

Transwest Air

As an alternative to flying from Chicago, you may also want to try searching for cheap flights from Chicago (ORD).
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