Southwest® flights from Oakland to Chicago (Midway) from $154*

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.

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$154
OFF

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

$109
OFF

$109 CHEAP FLIGHTS From Oakland To Chicago Midway (OAK

3 weeks from now

There is a maximum of 1 nonstop flight a day that takes off from Oakland and lands in Chicago Midway Airport, with an average flight time of 4h 05m. The most common departure time is …

kayak.com

$133
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$133 Flights From Oakland To Chicago (OAK To MDW) - Travelocity

3 weeks from now

$133 Search for cheap flights deals from OAK to MDW (Oakland Intl. to Midway Intl.). We offer cheap direct, non-stop flights including one way and roundtrip tickets.

travelocity.com

$166
OFF

Oakland Airport (OAK) To Chicago Midway Airport (MDW)

3 weeks from now

The cheapest way to get from Oakland Airport (OAK) to Chicago Midway Airport (MDW) costs only $166, and the quickest way takes just 4 hours. Find the travel option that best suits you.

rome2rio.com

$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

$109
OFF

$109+ Flights From Oakland, CA To Chicago Midway Airport

3 weeks from now

Find airfare and ticket deals for cheap flights from Oakland, CA to Chicago Midway Airport. Search flight deals from various travel partners with one click at $109. ... While on average our …

cheapflights.com

$164
OFF

Southwest® Flights From Oakland To Chicago (O'Hare) From $164*

3 weeks from now

Fly one-way from Oakland to Chicago (O'Hare) starting at $164. Bundle your Southwest Airlines® flight with a hotel or rental car booking and find even more savings. ... Chicago (MDW) …

southwest.com

FAQs about Southwest® flights from Oakland to Chicago (Midway) from $154* 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 to Oakland?

Southwest flies to over 100 destinations! Explore flights across our network. Oakland. See all our low fares from Oakland. Points bookings do not include taxes, fees, and other government/airport charges of at least $5.60 per one-way flight. Seats and days are limited. ...

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 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 many destinations does Southwest fly to?

Southwest flies to over 100 destinations! Explore flights across our network. Visit Chicago. Once dubbed freight handler to the nation, Chicago may not be the transportation hub of generations past but it’s still as much a hub of culture as it ever was. ...