Cheap Airfare from Chicago, IL (MDW) to Oakland, CA (OAK)

All flights from Chicago, IL (MDW) to Oakland, CA (OAK)

We found 69 matches for direct flights, non-stop flights, and last-minute flights between MDW and OAK. Use the table below to sort by number of connections or the time of day to find flights that leave MDW for OAK in the morning, afternoon, or evening.

Be sure to check our list of deals to see which airlines are offering special prices on airfare to Oakland, CA (OAK) or airfare from Chicago, IL (MDW).

Airline	Flt.	Departs	Time	Arrives	Time	Via	Compare prices
Southwest Airlines	3307	MDW	8:30am	OAK	11:10am	nonstop

Southwest Airlines	3802	MDW	10:00am	OAK	12:40pm	nonstop

Southwest Airlines	853	MDW	10:05am	OAK	2:15pm	direct

Southwest Airlines	559	MDW	10:50am	OAK	3:25pm	direct

Southwest Airlines	626	MDW	1:25pm	OAK	4:05pm	nonstop

Southwest Airlines	1691	MDW	2:05pm	OAK	4:45pm	nonstop

Southwest Airlines	1341	MDW	3:00pm	OAK	7:15pm	direct

Southwest Airlines	3976	MDW	3:35pm	OAK	7:55pm	direct

Southwest Airlines	1370	MDW	5:20pm	OAK	9:15pm	direct

Southwest Airlines	3010	MDW	6:00pm	OAK	8:40pm	nonstop

Southwest Airlines	926	MDW	7:25pm	OAK	10:05pm	nonstop

Southwest Airlines	3035	MDW	11:30am	OAK	5:35pm	Albuquerque (ABQ)

Southwest Airlines	416	MDW	2:50pm	OAK	9:15pm	Nashville (BNA)

Southwest Airlines	615	MDW	3:15pm	OAK	7:55pm	Nashville (BNA)

Southwest Airlines	1209	MDW	4:25pm	OAK	9:15pm	Nashville (BNA)

Southwest Airlines	974	MDW	10:15am	OAK	3:35pm	Denver (DEN)

Southwest Airlines	112	MDW	12:00pm	OAK	4:15pm	Denver (DEN)

Southwest Airlines	1377	MDW	2:45pm	OAK	8:00pm	Denver (DEN)

Southwest Airlines	201	MDW	3:15pm	OAK	8:00pm	Denver (DEN)

Frontier Airlines	859	MDW	3:50pm	OAK	7:57pm	Denver (DEN)	Search prices

Southwest Airlines	390	MDW	7:45am	OAK	2:15pm	Los Angeles (LAX)

Southwest Airlines	390	MDW	7:45am	OAK	1:15pm	Los Angeles (LAX)

Southwest Airlines	390	MDW	7:45am	OAK	12:15pm	Los Angeles (LAX)

Southwest Airlines	985	MDW	8:30am	OAK	1:15pm	Los Angeles (LAX)

Southwest Airlines	985	MDW	8:30am	OAK	2:15pm	Los Angeles (LAX)

Southwest Airlines	985	MDW	8:30am	OAK	3:15pm	Los Angeles (LAX)

Southwest Airlines	853	MDW	10:05am	OAK	4:15pm	Los Angeles (LAX)

Southwest Airlines	1801	MDW	11:40am	OAK	5:15pm	Los Angeles (LAX)

Southwest Airlines	1801	MDW	11:40am	OAK	6:15pm	Los Angeles (LAX)

Southwest Airlines	1801	MDW	11:40am	OAK	4:15pm	Los Angeles (LAX)

Southwest Airlines	1027	MDW	12:35pm	OAK	6:15pm	Los Angeles (LAX)

Southwest Airlines	1027	MDW	12:35pm	OAK	7:15pm	Los Angeles (LAX)

Southwest Airlines	1027	MDW	12:35pm	OAK	5:15pm	Los Angeles (LAX)

Southwest Airlines	1764	MDW	1:05pm	OAK	6:15pm	Los Angeles (LAX)

Southwest Airlines	1341	MDW	3:00pm	OAK	9:15pm	Los Angeles (LAX)

Southwest Airlines	1341	MDW	3:00pm	OAK	8:15pm	Los Angeles (LAX)

Southwest Airlines	1293	MDW	3:25pm	OAK	8:15pm	Los Angeles (LAX)

Southwest Airlines	1140	MDW	5:05pm	OAK	10:15pm	Los Angeles (LAX)

Southwest Airlines	513	MDW	8:55am	OAK	2:15pm	Kansas City (MCI)

Southwest Airlines	267	MDW	9:45am	OAK	2:15pm	Kansas City (MCI)

Southwest Airlines	2731	MDW	10:50am	OAK	5:00pm	Kansas City (MCI)

Southwest Airlines	375	MDW	12:30pm	OAK	5:00pm	Kansas City (MCI)

Southwest Airlines	2283	MDW	1:15pm	OAK	5:00pm	Kansas City (MCI)

Southwest Airlines	3899	MDW	8:30am	OAK	2:00pm	Portland (PDX)

Southwest Airlines	2950	MDW	1:55pm	OAK	8:40pm	Portland (PDX)

Southwest Airlines	2950	MDW	1:55pm	OAK	7:25pm	Portland (PDX)

Southwest Airlines	1862	MDW	7:00am	OAK	1:35pm	Phoenix (PHX)

Southwest Airlines	3519	MDW	7:45am	OAK	1:45pm	Phoenix (PHX)

Southwest Airlines	1024	MDW	8:10am	OAK	1:35pm	Phoenix (PHX)

Southwest Airlines	1962	MDW	9:15am	OAK	3:00pm	Phoenix (PHX)

Southwest Airlines	1668	MDW	10:40am	OAK	4:10pm	Phoenix (PHX)

Southwest Airlines	2675	MDW	12:40pm	OAK	5:55pm	Phoenix (PHX)

Southwest Airlines	1584	MDW	1:20pm	OAK	6:55pm	Phoenix (PHX)

Southwest Airlines	3729	MDW	3:25pm	OAK	10:10pm	Phoenix (PHX)

Southwest Airlines	3729	MDW	3:25pm	OAK	8:15pm	Phoenix (PHX)

Southwest Airlines	780	MDW	3:35pm	OAK	8:25pm	Phoenix (PHX)

Southwest Airlines	211	MDW	4:40pm	OAK	10:10pm	Phoenix (PHX)

Southwest Airlines	1050	MDW	5:35pm	OAK	10:10pm	Phoenix (PHX)

Southwest Airlines	1189	MDW	9:25am	OAK	3:05pm	San Diego (SAN)

Southwest Airlines	1189	MDW	9:25am	OAK	2:25pm	San Diego (SAN)

Southwest Airlines	402	MDW	10:05am	OAK	2:55pm	San Diego (SAN)

Southwest Airlines	3530	MDW	12:15pm	OAK	6:15pm	San Diego (SAN)

Southwest Airlines	3530	MDW	12:15pm	OAK	6:50pm	San Diego (SAN)

Southwest Airlines	3530	MDW	12:15pm	OAK	5:05pm	San Diego (SAN)

Southwest Airlines	1171	MDW	2:10pm	OAK	6:45pm	San Diego (SAN)

Southwest Airlines	1171	MDW	2:10pm	OAK	8:30pm	San Diego (SAN)

Southwest Airlines	3976	MDW	3:35pm	OAK	8:30pm	San Diego (SAN)

Southwest Airlines	3976	MDW	3:35pm	OAK	9:40pm	San Diego (SAN)

Southwest Airlines	3976	MDW	3:35pm	OAK	9:40pm	San Diego (SAN)

ABQ: Albuquerque International Airport
BNA: Nashville Metropolitan Airport
DEN: Denver International Airport
LAX: Los Angeles International Airport
MCI: Kansas City International Airport
MDW: Midway Airport
OAK: Metropolitan Oakland International Airport
PDX: Portland International Airport
PHX: Sky Harbor International Airport
SAN: San Diego International Airport

Note: Southwest Airlines tickets can be purchsed at Southwest.com.

Frontier Airlines
Phone #: 800-432-1359
URL: http://www.flyfrontier.com
Southwest Airlines
Phone #: 800-435-9792
URL: http://www.iflyswa.com

For more options, try adding these alternate airports :

Or check your return flight :

Disclaimer

Smarter Travel Media LLC and Innovata, LLC have used their best efforts to collect and prepare material for inclusion in this travel directory, and cannot warrant that the information is totally complete or accurate.

Data shown in this directory are for information only. Neither Innovata nor Smarter Travel Media LLC will be responsible for the failure of flights to operate at the times listed in this publication, nor for errors herein, nor for failure to make connections with planes, nor for any omissions of data.

Schedules are subject to change without notice. Schedules shown are based on expected flight times as presented to Smarter Travel Media LLC. Weather and other factors may affect operating conditions, and departures and arrivals cannot be guaranteed. The mileage shown is approximate, based on industry standards, and will vary from actual airline mileage received for each flight segment.

Smarter Travel Media LLC and Innovata disclaim any liability to any person for loss or damage caused by errors or omissions in the data contained on this page, whether such errors or omissions result from negligence, accident or other cause.

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Other Flights From MDW

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Cheap airfare from MDW to PUJ (1 flights)

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Fall in love with Virginia's capital city.
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Greensboro combines a small-town feel with big-city attractions.

Hotels

Crowne Plaza Campbell House
1375 South Broadway
Lexington, KY
5 traveler comments
Number of Rooms: 290
Holiday Inn Indianapolis East
6990 E. 21st Street
I70 & Shadeland Avenue
Indianapolis, IN
5 traveler comments
Number of Rooms: 184
Number of Floors: 6
Red Roof Inn Columbus Ohio State University
441 Ackerman Road
Columbus, OH
5 traveler comments
Number of Rooms: 115
Doubletree Hotel Chattanooga
407 Chestnut Street
Chattanooga, TN
5 traveler comments
Number of Rooms: 186
Number of Floors: 12
Country Inn & Suites University Place
131 E McCullough Dr
Charlotte, NC
5 traveler comments
Number of Rooms: 100
Number of Floors: 3
Charlotte Marriott City Center
100 West Trade St
Charlotte, NC
5 traveler comments
Number of Rooms: 438
Number of Floors: 19
Doubletree Hotel Charlotte - Gateway Village
895 W Trade St
Charlotte, NC
5 traveler comments
Number of Rooms: 187
Hampton Inn & Suites Boston Crosstown Center
811 Massachusetts Avenue
Boston, MA
5 traveler comments
Number of Rooms: 175
Renaissance Waverly Hotel
2450 Galleria Pkwy
Atlanta, GA
5 traveler comments
Number of Rooms: 521
Number of Floors: 14
Crowne Plaza Atlanta Airport
1325 Virginia Avenue
Atlanta, GA
5 traveler comments

*Taxes and fees are additional: Learn how they increase your airfare

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Current departures: Chicago (MDW) Chicago (CGX) [9 miles from MDW] Chicago (ORD) [16 miles from MDW]	Current arrivals: Oakland (OAK) San Francisco (SFO) [11 miles from OAK] San Jose (SJC) [30 miles from OAK]