Southwest® flights from Chicago (Midway) to Oakland from $174*

Fly one-way from Chicago (Midway) to Oakland starting at $174. Bundle your Southwest Airlines® flight with a hotel or rental car booking and find even more savings.

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$174
OFF

Southwest® Flights From Chicago (Midway) To Oakland From $174*

3 weeks from now

Fly one-way from Chicago (Midway) to Oakland starting at $174. Bundle your Southwest Airlines® flight with a hotel or rental car booking and find even more savings.

southwest.com

$129
OFF

$129 CHEAP FLIGHTS From Chicago Midway To Oakland (MDW

3 weeks from now

There is a maximum of 1 nonstop flight a day that takes off from Chicago Midway Airport and lands in Oakland, with an average flight time of 4h 52m. The most common departure time is …

kayak.com

$129
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$129 Cheap Flights From Chicago (MDW) To Oakland (OAK)

3 weeks from now

Cheap Flights from Chicago (MDW) to Oakland (OAK) start at $129 for one-way and $257 for round trip. Earn your airline miles on top of our rewards!

expedia.com

$134
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$134+ Flights From Chicago Midway Airport To Oakland, CA

3 weeks from now

4 days ago · Most accurate provider: When it comes to deals on Chicago Midway Airport-Oakland, California flights, users find the pricing of FlightHub to be most consistent on …

cheapflights.com

$134
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$134 Flights From Chicago To Oakland (MDW To OAK) - Travelocity

3 weeks from now

$134 Search for cheap flights deals from MDW to OAK (Midway Intl. to Oakland Intl.). We offer cheap direct, non-stop flights including one way and roundtrip tickets.

travelocity.com

$154
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Southwest® Flights From Oakland To Chicago (Midway) From $154*

3 weeks from now

Fly one-way from Oakland to Chicago (Midway) starting at $154. Bundle your Southwest Airlines® flight with a hotel or rental car booking and find even more savings.

southwest.com

$174
OFF

Cheap Flights From Chicago (O'Hare) To San Francisco (SFO) From …

3 weeks from now

Fly one-way from Chicago (O'Hare) to San Francisco (SFO) starting at $174. Bundle your Southwest Airlines® flight with a hotel or rental car booking and find even more savings.

southwest.com

$196
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Southwest® Flights From Chicago (Midway) To Sacramento From …

3 weeks from now

Fly one-way from Chicago (Midway) to Sacramento starting at $196. ... Oakland (OAK) San Francisco (SFO) Burbank (BUR) Explore our route map featuring over 120 destinations! † …

southwest.com

FAQs about Southwest® flights from Chicago (Midway) to Oakland from $174* Coupon?

Does Southwest fly to Chicago Midway International Airport?

Southwest Airlines is proud to serve Chicago Midway International Airport. Boarding a Southwest flight departing Midway is a snap—just hop on the “L” train! The Orange Line will take you directly to the airport, the first stop on your adventure beyond the Second City. Of course, long-term parking and calling a car are always options, too. ...

Does Southwest fly out of Chicago?

There’s so much world out there to explore beyond the Chicagoland area, and Southwest can take you there. And since Chicago Midway International Airport is a Southwest Airlines hub, many of those flights out of Chi-Town are direct! It’s time for a change of scenery. ...

How do I get from Midway Airport to Chicago?

Traveling from Midway. Southwest Airlines is proud to serve Chicago Midway International Airport. Boarding a Southwest flight departing Midway is a snap—just hop on the “L” train! The Orange Line will take you directly to the airport, the first stop on your adventure beyond the Second City. ...

How do I Check my Flight to Chicago Midway Airport (MDW)?

Check the status of your flight to Chicago Midway Airport (MDW) using the information on our departures page. The data on departures times and status is frequently updated in real time. To simplify your search, you have the option to filter results by Airline or Time period, or you can use the search box to find your flight directly. ...

How do I find the lowest fares on a Southwest flight?

Plug them into the Low Fare Calendar and see the lowest fares available within your travel window. You may also want to browse Southwest Vacations ® to see special offers and package deals on flights, hotels, rental cars, and more. Explore your options and book your Chicago (Midway) to Oakland flight with Southwest today! ...

How far is Oakland International Airport from downtown?

Oakland International Airport is a mere 10 miles outside of downtown Oakland. Hop on the BART or rent a car and get going! At Southwest, we know it takes more than great deals on Oakland airfares and convenient scheduling options to make your trip memorable. ...