$63 Cheap flights from Oakland Intl. to Midway Intl. (OAK to MDW)

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Find The Best Dates To Fly from Oakland Intl. to Midway Intl.

Compare Flight Prices from Oakland to Chicago

Affordable Airfare Tickets from OAK to MDW Airport

The cheapest flights to Midway Intl. found within the past 7 days were $217 round trip and $63 one way. Prices and availability subject to change. Additional terms may apply.

Wed, Aug 20 - Tue, Aug 26
OAK
Oakland
MDW
Chicago
$217 Roundtrip, found 5 days ago
$217
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Aug 20 from Oakland to Chicago, returning Tue, Aug 26, priced at $217 found 5 days ago
Wed, Aug 20 - Tue, Aug 26
OAK
Oakland
MDW
Chicago
$222 Roundtrip, found 5 days ago
$222
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Aug 20 from Oakland to Chicago, returning Tue, Aug 26, priced at $222 found 5 days ago
Wed, Aug 20 - Tue, Aug 26
OAK
Oakland
MDW
Chicago
$227 Roundtrip, found 5 days ago
$227
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Aug 20 from Oakland to Chicago, returning Tue, Aug 26, priced at $227 found 5 days ago
Wed, Aug 20 - Tue, Aug 26
OAK
Oakland
MDW
Chicago
$232 Roundtrip, found 5 days ago
$232
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Aug 20 from Oakland to Chicago, returning Tue, Aug 26, priced at $232 found 5 days ago
Wed, Aug 20 - Tue, Aug 26
OAK
Oakland
MDW
Chicago
$238 Roundtrip, found 5 days ago
$238
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Aug 20 from Oakland to Chicago, returning Tue, Aug 26, priced at $238 found 5 days ago
Sat, Aug 30 - Wed, Sep 3
OAK
Oakland
MDW
Chicago
$285 Roundtrip, found 22 hours ago
$285
Roundtrip
found 22 hours ago
Select Southwest Airlines flight, departing Sat, Aug 30 from Oakland to Chicago, returning Wed, Sep 3, priced at $285 found 22 hours ago
Sat, Aug 30 - Wed, Sep 3
OAK
Oakland
MDW
Chicago
$290 Roundtrip, found 22 hours ago
$290
Roundtrip
found 22 hours ago
Select Southwest Airlines flight, departing Sat, Aug 30 from Oakland to Chicago, returning Wed, Sep 3, priced at $290 found 22 hours ago
Mon, Aug 18 - Fri, Aug 22
OAK
Oakland
MDW
Chicago
$291 Roundtrip, found 2 days ago
$291
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Mon, Aug 18 from Oakland to Chicago, returning Fri, Aug 22, priced at $291 found 2 days ago
Mon, Aug 18 - Tue, Aug 19
OAK
Oakland
MDW
Chicago
$293 Roundtrip, found 2 days ago
$293
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Mon, Aug 18 from Oakland to Chicago, returning Tue, Aug 19, priced at $293 found 2 days ago
Sat, Aug 30 - Wed, Sep 3
OAK
Oakland
MDW
Chicago
$295 Roundtrip, found 22 hours ago
$295
Roundtrip
found 22 hours ago
Select Southwest Airlines flight, departing Sat, Aug 30 from Oakland to Chicago, returning Wed, Sep 3, priced at $295 found 22 hours ago

Midway Intl. flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
per person
Aug 29 - Sep 1
found 14 hours ago
Roundtrip non-stop flight included
Oakland (OAK) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
per person
Aug 29 - Sep 1
found 14 hours ago
Roundtrip non-stop flight included
Oakland (OAK) to Chicago (ORD)
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
per person
Aug 29 - Sep 1
found 14 hours ago
Roundtrip non-stop flight included
Oakland (OAK) to Chicago (ORD)
Arlo Chicago

Arlo Chicago

4 out of 5
per person
Aug 29 - Sep 1
found 14 hours ago
Roundtrip non-stop flight included
Oakland (OAK) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
per person
Aug 29 - Sep 1
found 14 hours ago
Roundtrip non-stop flight included
Oakland (OAK) to Chicago (ORD)
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Flight information from Oakland to Chicago

 

Traveling From
Oakland Intl.
Traveling To
Midway Intl.
Shortest Flight Time
 hours mins
Earliest Departure Time
Latest Departure Time
Lowest Flight Price
$217