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

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Wed 12/13
Wed 12/20
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Good to Know

Average Price:
$360
(avg. price over the last 2 weeks)
Good Deal:
$245
or less (round trip)

When to Book Flights from Oakland to Chicago Midway

Flight prices as travel date approaches
-1 day
-2 days

Top tips for Finding a Cheap Flight

Looking for a cheap flight? 25% of our users found flights on this route for $245 or less.
The cheapest flight from Oakland to Chicago Midway was found 49 days before departure, on average.
Book at least 1 week before departure in order to get a below-average price.
Morning departure is around 10% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for Booking Oakland to Chicago Midway Flights

How long does a flight from Oakland to Chicago Midway take?
An average nonstop flight takes 4h 00m, covering a distance of 1840 miles.
How many flights are there between Oakland and Chicago Midway?
There are 71 (nonstop) flights between Oakland and Chicago Midway per week, averaging 11 per day.
Which airlines provide the cheapest flights from Oakland to Chicago Midway?
In the past 3 days, the cheapest round-trip tickets were found on Southwest ($255), Delta ($412) and Multiple Airlines ($610).
Do I need a passport to fly between Oakland and Chicago Midway?
No.
Which airlines fly most frequently between Oakland and Chicago Midway?
Southwest (10 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly Oakland to Chicago Midway?
For Oakland to Chicago Midway, Saturday is the cheapest day to fly on average and Friday is the most expensive. Flying from Chicago Midway back to Oakland, the best deals are generally found on Saturday, with Friday being the most expensive.

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

Airports
Origin
Oakland
$255
only
$255
Destination
Chicago
$255
only
$255
Sat, Jan 20
OAK
MDW
4h 05m
Tue, Jan 23
MDW
OAK
4h 50m
Trip: 4 days
8.1ExcellentShow reviews
Overall 8.1 Excellent
Based on 5 reviews
Boarding
8.8
Comfort
8.5
Crew
9.0
Entertainment
8.0
Food
7.9
DAL
AUS
Excellent 10.0

Southwest is always great. Best part is they are always on time

OAK
MDW
Excellent 10.0

Easy

RDU
MDW
Excellent 10.0

On time. Fun crew.

SAT
MCO
Excellent 10.0

Great service

MSY
DAL
Excellent 10.0

Great!

N/a

Wed, Apr 11
OAK
MDW
9h 57m
Wed, Apr 18
MDW
OAK
9h 07m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14179 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
YYZ
YQB
Okay 5.0

They had to change tires before we lelt in Toronto. And we spent more than one hour on the tarmac.

MCO
YYZ
Excellent 8.3

On time as scheduled.

N/A

SFO
LAX
Excellent 10.0

Excellent service and upgraded snacks in economy

Nothing

MEX
JFK
Mediocre 3.6

Nothing really.

Boarding process was horribly handled. Food was inadequate. Stewardess was saccharine. Bathroom door didn’t shut completely. I was told this wasn’t an international flight and therefore no free alcohol. Aero Mexico flight to Mexico City had much better food, free alcohol and more attentive service personnel. Also delays because of equipment problems.

LAX
SJC
Okay 4.0

On time arrival

Small aircraft. Loud engine noise. Biased treatment for tickets booked on non Delta sites

Tue, Feb 20
OAK
MDW
4h 05m
Mon, Feb 26
MDW
OAK
4h 50m
Trip: 7 days
8.1ExcellentShow reviews
Overall 8.1 Excellent
Based on 5 reviews
Boarding
8.8
Comfort
8.5
Crew
9.0
Entertainment
8.0
Food
7.9
LAS
BWI
Excellent 10.0

Plane was on time. Boarding was seamless. Crew was very polite and attentive. I even had two coffees with hazelnut creamer. I love southwest and how they continue to offer amenities at no additional fee!

MSY
DAL
Excellent 10.0

Great!

N/a

TPA
MKE
Good 7.3

Crew was great

Flight delayed slightly, not too bad, but it seemed to take a long time to get the plane boarded, which is unusual from my experience with Southwest

DAL
AUS
Excellent 10.0

Southwest is always great. Best part is they are always on time

DAL
MSY
Excellent 10.0

Great

Fri, Dec 15
OAK
MDW
5h 55m
Mon, Dec 18
MDW
OAK
26h 54m
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Feb 8
OAK
MDW
4h 05m
Mon, Feb 12
MDW
OAK
4h 50m
Trip: 5 days
8.1ExcellentShow reviews
Overall 8.1 Excellent
Based on 5 reviews
Boarding
8.8
Comfort
8.5
Crew
9.0
Entertainment
8.0
Food
7.9
PDX
SJC
Excellent 8.0

The plane was completely full and it was comfortable. The flight attendants were friendly and always had a smile. Very professional.

One of the flight attendants wanted to be a stand up Comedian. It was a little trying but my wife liked his routine more than I did.

DAL
AUS
Excellent 10.0

Southwest is always great. Best part is they are always on time

OAK
MDW
Excellent 10.0

Easy

RDU
MDW
Excellent 10.0

On time. Fun crew.

MSY
DAL
Excellent 10.0

Great!

N/a

Tue, Mar 6
OAK
MDW
4h 10m
Thu, Mar 8
MDW
OAK
4h 40m
Trip: 3 days
8.1ExcellentShow reviews
Overall 8.1 Excellent
Based on 5 reviews
Boarding
8.8
Comfort
8.5
Crew
9.0
Entertainment
8.0
Food
7.9
LAS
BWI
Excellent 10.0

Plane was on time. Boarding was seamless. Crew was very polite and attentive. I even had two coffees with hazelnut creamer. I love southwest and how they continue to offer amenities at no additional fee!

RDU
MDW
Excellent 10.0

On time. Fun crew.

MSY
DAL
Excellent 10.0

Great!

N/a

PDX
SJC
Excellent 8.0

The plane was completely full and it was comfortable. The flight attendants were friendly and always had a smile. Very professional.

One of the flight attendants wanted to be a stand up Comedian. It was a little trying but my wife liked his routine more than I did.

ISP
TPA
Good 7.6

I like that two checked in bags are included in the price. ISP is close to my home and easy to get in and out of. The airline is always on time, even when there is a late departure.

The seats have changed. They are narrower in width, the knee room is less, the staff while still professional is more serious, not as fun and friendly. Spicy snacks and peanuts are limited. Cookies go better with tea and coffee on the late night flights.

Thu, Mar 8
OAK
MDW
4h 00m
Tue, Mar 13
MDW
OAK
4h 45m
Trip: 5 days
8.1ExcellentShow reviews
Overall 8.1 Excellent
Based on 5 reviews
Boarding
8.8
Comfort
8.5
Crew
9.0
Entertainment
8.0
Food
7.9
TPA
MKE
Good 7.3

Crew was great

Flight delayed slightly, not too bad, but it seemed to take a long time to get the plane boarded, which is unusual from my experience with Southwest

SAT
MCO
Excellent 10.0

Great service

BNA
CHS
Excellent 10.0

Prompt boarding and smooth flight

DAL
MSY
Excellent 10.0

Great

PDX
SJC
Excellent 8.0

The plane was completely full and it was comfortable. The flight attendants were friendly and always had a smile. Very professional.

One of the flight attendants wanted to be a stand up Comedian. It was a little trying but my wife liked his routine more than I did.

Fri, Jan 5
OAK
MDW
10h 23m
Sun, Jan 7
MDW
OAK
10h 06m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14179 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SFO
DTW
Okay 4.0

Arrived.

Late, slow, de-icing in Detroit took nearly an hour!

ATL
MEX
Excellent 8.6

Sandwich for dinner

LHR
JFK
Good 7.0

Delays!

MEX
JFK
Mediocre 3.6

Nothing really.

Boarding process was horribly handled. Food was inadequate. Stewardess was saccharine. Bathroom door didn’t shut completely. I was told this wasn’t an international flight and therefore no free alcohol. Aero Mexico flight to Mexico City had much better food, free alcohol and more attentive service personnel. Also delays because of equipment problems.

FLL
ATL
Good 6.0

The plane was really cool. Some more advanced technologies than other Airline companies. Crew was good too.

Issue happened with my landing. Didn't make it in time to next gate. Delta did everything they could to blame me, insulted me on The phone and definitely provided the worst customer service

Thu, Dec 28
OAK
MDW
4h 00m
Tue, Jan 2
MDW
OAK
4h 45m
Trip: 6 days
8.1ExcellentShow reviews
Overall 8.1 Excellent
Based on 5 reviews
Boarding
8.8
Comfort
8.5
Crew
9.0
Entertainment
8.0
Food
7.9
BNA
CHS
Excellent 10.0

Prompt boarding and smooth flight

RDU
MDW
Excellent 10.0

On time. Fun crew.

MSY
DAL
Excellent 10.0

Great!

N/a

ISP
TPA
Good 7.6

I like that two checked in bags are included in the price. ISP is close to my home and easy to get in and out of. The airline is always on time, even when there is a late departure.

The seats have changed. They are narrower in width, the knee room is less, the staff while still professional is more serious, not as fun and friendly. Spicy snacks and peanuts are limited. Cookies go better with tea and coffee on the late night flights.

TPA
MKE
Good 7.3

Crew was great

Flight delayed slightly, not too bad, but it seemed to take a long time to get the plane boarded, which is unusual from my experience with Southwest

Sat, Dec 23
OAK
MDW
8h 41m
Sat, Dec 30
MDW
OAK
10h 47m
$1485
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14179 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
YYZ
YQB
Okay 5.0

They had to change tires before we lelt in Toronto. And we spent more than one hour on the tarmac.

LAX
OAK
Mediocre 2.0

Due to the earthquakes, the film festival I was going to was cancelled. Ten days prior to the flight I called AeroMexico to cancel and they said there would be a cancellation penalty, which was fine. When I tried to redeem my credit, they said there was also an additional "No-show fee" even though I called to cancel 10 days prior, which left a total of $70 credit after all their penalties. I called and emailed to complain but they did nothing but pass me to someone else who was equally unhelpful. I will never fly AeroMexico for any reason in the future.

SFO
LAX
Excellent 10.0

Excellent service and upgraded snacks in economy

Nothing

ATL
MEX
Excellent 8.6

Sandwich for dinner

MEX
JFK
Mediocre 3.6

Nothing really.

Boarding process was horribly handled. Food was inadequate. Stewardess was saccharine. Bathroom door didn’t shut completely. I was told this wasn’t an international flight and therefore no free alcohol. Aero Mexico flight to Mexico City had much better food, free alcohol and more attentive service personnel. Also delays because of equipment problems.

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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.