Find Cheap Flights from Chicago Midway to Oakland (MDW - OAK)

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Tue 12/19
Tue 12/26
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Looking for a cheap flight? 25% of our users found flights on this route for $244 or less.

FAQs for Booking Chicago Midway to Oakland Flights

How long does a flight from Chicago Midway to Oakland take?
An average nonstop flight takes 7h 41m, covering a distance of 1840 miles.
How many flights are there between Chicago Midway and Oakland?
There are 57 (nonstop) flights between Chicago Midway and Oakland per week, averaging 8 per day.
Which airlines provide the cheapest flights from Chicago Midway to Oakland?
In the past 3 days, the cheapest round-trip tickets were found on Delta ($277)
Do I need a passport to fly between Chicago Midway and Oakland?
No.
Which airlines fly most frequently between Chicago Midway and Oakland?
Southwest (8 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly Chicago Midway to Oakland?
For Chicago Midway to Oakland, Wednesday is the cheapest day to fly on average and Friday is the most expensive. Flying from Oakland back to Chicago Midway, the best deals are generally found on Wednesday, with Saturday being the most expensive.

Book cheap flights from Chicago Midway to Oakland (round-trip)

Airports
Origin
Chicago
$277
only
$277
Destination
Oakland
$277
only
$277
Wed, Jan 10
MDW
OAK
13h 09m
Thu, Jan 11
OAK
MDW
11h 38m
Trip: 2 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14326 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LAX
JFK
Okay 4.0

average food. poor corrdination for the connection transfer

JFK
CDG
Excellent 9.6

Food and movies were good.

Didn't leave on time.

LGA
DTW
Good 6.6

The flight was practically empty!

Paid for comfort, Delta offered free drinks to everyone. Unfortunately though the flight attendant did not bring us the alcohol we ordered and mixed 3 different kinds of whiskey into two glasses! We always are given our bottles separate from the mixer. Oh well. Did to being in so late it took us an hour to get a cab in Detroit.

CHS
ATL
Mediocre 2.0

My flight got cancel two days in a row due to outrage power in atlanta.

OKC
DTW
Mediocre 2.0

flight was canceled

Fri, May 4
MDW
OAK
10h 45m
Mon, May 7
OAK
MDW
11h 02m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14326 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MEX
BJX
Okay 4.0

Horrible experience! Flight was delayed over an hour with no announcement. Seat was reassigned from front aisle seat to rear window Seat. Fortunately, it was a short fkight.

OKC
DTW
Mediocre 2.0

flight was canceled

LAX
MSP
Excellent 8.0

The snack variety

My headphone jack was broken :(

AZO
DTW
Excellent 10.0

Upgraded. Arrived early

No entertainment system even in 1rst class

JFK
CDG
Excellent 9.6

Food and movies were good.

Didn't leave on time.

Thu, Mar 22
MDW
OAK
12h 15m
Wed, Mar 28
OAK
MDW
14h 08m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14326 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
CHS
ATL
Mediocre 2.0

My flight got cancel two days in a row due to outrage power in atlanta.

LAX
JFK
Okay 4.0

average food. poor corrdination for the connection transfer

MYR
ATL
Good 7.3

Flight was 3 hours late leaving due to frost on wings. De icing truck wouldn’t work so they waited until sunrise and parked the plane in the sun. Real hi tech solution.

MEX
BJX
Okay 4.0

Horrible experience! Flight was delayed over an hour with no announcement. Seat was reassigned from front aisle seat to rear window Seat. Fortunately, it was a short fkight.

AZO
DTW
Excellent 10.0

Upgraded. Arrived early

No entertainment system even in 1rst class

Thu, Apr 26
MDW
OAK
9h 07m
Mon, Apr 30
OAK
MDW
12h 13m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14326 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SAT
JFK
Good 7.6

Excellent leg room. Comfy seat

Seat couldn't recline back. Was a little uncomfortable for a long flight. Chair had crumbs on it before I sat down-it was easily wiped away meaning no one had cleaned the chairs or looked at them beforehand. Absolutely freezing. Wearing long socks and boots and my feet still felt frozen by the end.

JFK
BOS
Good 7.6

Seats were very comfortable. Was able to recline back and had excellent leg room. Area looked clean and organized.

Captain didn't say much before or during the flight like most do. Not a big deal-it was a short flight.

MEX
BJX
Okay 4.0

Horrible experience! Flight was delayed over an hour with no announcement. Seat was reassigned from front aisle seat to rear window Seat. Fortunately, it was a short fkight.

JFK
CDG
Excellent 9.6

Food and movies were good.

Didn't leave on time.

LAX
JFK
Okay 4.0

average food. poor corrdination for the connection transfer

Tue, May 15
MDW
OAK
10h 45m
Sun, May 20
OAK
MDW
11h 02m
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14326 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
OKC
DTW
Mediocre 2.0

flight was canceled

MYR
ATL
Good 7.3

Flight was 3 hours late leaving due to frost on wings. De icing truck wouldn’t work so they waited until sunrise and parked the plane in the sun. Real hi tech solution.

SAT
JFK
Good 7.6

Excellent leg room. Comfy seat

Seat couldn't recline back. Was a little uncomfortable for a long flight. Chair had crumbs on it before I sat down-it was easily wiped away meaning no one had cleaned the chairs or looked at them beforehand. Absolutely freezing. Wearing long socks and boots and my feet still felt frozen by the end.

JFK
BOS
Good 7.6

Seats were very comfortable. Was able to recline back and had excellent leg room. Area looked clean and organized.

Captain didn't say much before or during the flight like most do. Not a big deal-it was a short flight.

LGA
DTW
Good 6.6

The flight was practically empty!

Paid for comfort, Delta offered free drinks to everyone. Unfortunately though the flight attendant did not bring us the alcohol we ordered and mixed 3 different kinds of whiskey into two glasses! We always are given our bottles separate from the mixer. Oh well. Did to being in so late it took us an hour to get a cab in Detroit.

Mon, Feb 19
MDW
OAK
10h 45m
Sat, Feb 24
OAK
MDW
13h 35m
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14326 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
OKC
DTW
Mediocre 2.0

flight was canceled

JFK
CDG
Excellent 9.6

Food and movies were good.

Didn't leave on time.

LGA
DTW
Good 6.6

The flight was practically empty!

Paid for comfort, Delta offered free drinks to everyone. Unfortunately though the flight attendant did not bring us the alcohol we ordered and mixed 3 different kinds of whiskey into two glasses! We always are given our bottles separate from the mixer. Oh well. Did to being in so late it took us an hour to get a cab in Detroit.

AZO
DTW
Excellent 10.0

Upgraded. Arrived early

No entertainment system even in 1rst class

MEX
BJX
Okay 4.0

Horrible experience! Flight was delayed over an hour with no announcement. Seat was reassigned from front aisle seat to rear window Seat. Fortunately, it was a short fkight.

Wed, Jun 13
MDW
OAK
7h 41m
Sun, Jun 17
OAK
MDW
11h 11m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14326 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
BOS
Good 7.6

Seats were very comfortable. Was able to recline back and had excellent leg room. Area looked clean and organized.

Captain didn't say much before or during the flight like most do. Not a big deal-it was a short flight.

SAT
JFK
Good 7.6

Excellent leg room. Comfy seat

Seat couldn't recline back. Was a little uncomfortable for a long flight. Chair had crumbs on it before I sat down-it was easily wiped away meaning no one had cleaned the chairs or looked at them beforehand. Absolutely freezing. Wearing long socks and boots and my feet still felt frozen by the end.

LGA
DTW
Good 6.6

The flight was practically empty!

Paid for comfort, Delta offered free drinks to everyone. Unfortunately though the flight attendant did not bring us the alcohol we ordered and mixed 3 different kinds of whiskey into two glasses! We always are given our bottles separate from the mixer. Oh well. Did to being in so late it took us an hour to get a cab in Detroit.

LAX
MSP
Excellent 8.0

The snack variety

My headphone jack was broken :(

CHS
ATL
Mediocre 2.0

My flight got cancel two days in a row due to outrage power in atlanta.

Sat, Dec 30
MDW
OAK
10h 17m
Sat, Jan 6
OAK
MDW
8h 50m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14326 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LIT
ATL
Good 6.6

WiFi doesn’t work.

LAX
JFK
Okay 4.0

average food. poor corrdination for the connection transfer

MYR
ATL
Good 7.3

Flight was 3 hours late leaving due to frost on wings. De icing truck wouldn’t work so they waited until sunrise and parked the plane in the sun. Real hi tech solution.

JFK
BOS
Good 7.6

Seats were very comfortable. Was able to recline back and had excellent leg room. Area looked clean and organized.

Captain didn't say much before or during the flight like most do. Not a big deal-it was a short flight.

AZO
DTW
Excellent 10.0

Upgraded. Arrived early

No entertainment system even in 1rst class

Fri, Dec 22
MDW
OAK
10h 13m
Sun, Dec 31
OAK
MDW
11h 26m
Trip: 10 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14326 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
OKC
DTW
Mediocre 2.0

flight was canceled

CHS
ATL
Mediocre 2.0

My flight got cancel two days in a row due to outrage power in atlanta.

LIT
ATL
Good 6.6

WiFi doesn’t work.

JFK
BOS
Good 7.6

Seats were very comfortable. Was able to recline back and had excellent leg room. Area looked clean and organized.

Captain didn't say much before or during the flight like most do. Not a big deal-it was a short flight.

SAT
JFK
Good 7.6

Excellent leg room. Comfy seat

Seat couldn't recline back. Was a little uncomfortable for a long flight. Chair had crumbs on it before I sat down-it was easily wiped away meaning no one had cleaned the chairs or looked at them beforehand. Absolutely freezing. Wearing long socks and boots and my feet still felt frozen by the end.

Fri, Dec 29
MDW
OAK
10h 13m
Sun, Dec 31
OAK
MDW
10h 38m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14326 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
BOS
Good 7.6

Seats were very comfortable. Was able to recline back and had excellent leg room. Area looked clean and organized.

Captain didn't say much before or during the flight like most do. Not a big deal-it was a short flight.

MEX
BJX
Okay 4.0

Horrible experience! Flight was delayed over an hour with no announcement. Seat was reassigned from front aisle seat to rear window Seat. Fortunately, it was a short fkight.

LAX
JFK
Okay 4.0

average food. poor corrdination for the connection transfer

AZO
DTW
Excellent 10.0

Upgraded. Arrived early

No entertainment system even in 1rst class

JFK
CDG
Excellent 9.6

Food and movies were good.

Didn't leave on time.

*
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The fares displayed include all taxes and fees for economy class travel and were found by the provider in the last 72 hours. Seats are limited and may not be available on all flights and days. Fares are subject to change and may not be available on all flights or dates of travel. Some carriers charge additional fees for extra checked bags. Please check the carriers' sites.