Find Cheap Flights from Chicago to Oakland (CHI - OAK)

Search hundreds of travel sites at once for deals on flights to Oakland

Wed 12/13
Wed 12/20
Any month
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Good to Know

Low Season:
September
Best time to beat the crowds
4%
expected price decrease
High Season:
December
Most popular time to fly
30%
expected price increase
Average Price:
$276
(avg. price over the last 2 weeks)
Good Deal:
$193
or less (round trip)

When to Book Flights from Chicago to Oakland

Average price per month
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 $193 or less.
The cheapest flight from Chicago to Oakland was found 62 days before departure, on average.
Book at least 2 weeks before departure in order to get a below-average price.
On average*, there is no price difference when choosing to fly in the morning or the evening on this flight route.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for Booking Chicago to Oakland Flights

How long does a flight from Chicago to Oakland take?
An average nonstop flight takes 4h 35m, covering a distance of 1846 miles.
How many flights are there between Chicago and Oakland?
There are 72 (nonstop) flights between Chicago and Oakland per week, averaging 11 per day.
Which airlines provide the cheapest flights from Chicago to Oakland?
In the past 3 days, the cheapest round-trip tickets were found on Spirit Airlines ($131) and Multiple Airlines ($205)
Do I need a passport to fly between Chicago and Oakland?
No.
Which airlines fly most frequently between Chicago and Oakland?
Southwest (10 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly Chicago to Oakland?
For Chicago to Oakland, Saturday is the cheapest day to fly on average and Tuesday is the most expensive. Flying from Oakland back to Chicago, the best deals are generally found on Thursday, with Sunday being the most expensive.

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

Airports
Origin
Chicago
$131
only
$131
Destination
Oakland
$131
only
$131
Sat, Apr 14
ORD
OAK
4h 35m
Mon, Apr 16
OAK
ORD
4h 18m
Trip: 3 days
5.6OkayShow reviews
Overall 5.6 Okay
Based on 198 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
ORD
OAK
Excellent 8.3

No nonesense, on time, friendly, attentive, dialed in process

Really barebones, no wifi, no reclining, baggage fees seem excessive, no entertainment, USB power would be nice I'd pay $5 each way for that

ORD
OAK
Excellent 8.0

Smooth flights.

15 minute delay leaving. 2 hour delay coming back.

ORD
OAK
Good 6.0

Departed on time; arrived on time

Uncomfortable seats; no storage pocket; insufficient tray table

ORD
OAK
Good 6.0

There wasnt any power outlet and wifi

ORD
OAK
Excellent 8.0

Every thing on time all was good.

Mon, Feb 12
ORD
OAK
21h 11m
Wed, Feb 14
OAK
ORD
15h 04m
Trip: 3 days
Overall 0.0 Poor
Based on 0 reviews
Tue, May 8
ORD
OAK
4h 35m
Sat, May 12
OAK
ORD
4h 18m
Trip: 5 days
5.6OkayShow reviews
Overall 5.6 Okay
Based on 198 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
ORD
OAK
Good 7.6

The flights left on time and arrived earlier than posted time. Flight was very smooth and the Landing was very gentle. airplane to clean.

I understand the get from A to B as cheaply as possible but even the food you order was just limited to snacks. But this is not a deal breaker.

ORD
OAK
Excellent 8.0

Every thing on time all was good.

ORD
OAK
Excellent 9.5

Flight on time. Crew very friendly and fun. I knew what to expect.

I'm a grandma but have reasonably decent tech skills. I find Spirit's website a little difficult to maneuver in. I think they are trying to be too "cute" and have lost a little intuitiveness.

ORD
OAK
Okay 4.0

Onboarding was very simple and fast. It took less than 20 minutes

My back was completely messed up from those seats. It was too long a flight to have those hard seats. The pull down tray was also uncomfortable to use for my laptop or not ok.

ORD
OAK
Good 6.0

Departed on time; arrived on time

Uncomfortable seats; no storage pocket; insufficient tray table

Mon, Apr 16
ORD
OAK
4h 35m
Wed, Apr 18
OAK
ORD
4h 18m
Trip: 3 days
5.6OkayShow reviews
Overall 5.6 Okay
Based on 198 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
ORD
OAK
Mediocre 2.0

Customer unfriendly

ORD
OAK
Good 7.6

The flights left on time and arrived earlier than posted time. Flight was very smooth and the Landing was very gentle. airplane to clean.

I understand the get from A to B as cheaply as possible but even the food you order was just limited to snacks. But this is not a deal breaker.

ORD
OAK
Good 6.0

There wasnt any power outlet and wifi

ORD
OAK
Excellent 8.0

Every thing on time all was good.

ORD
OAK
Excellent 8.0

Smooth flights.

15 minute delay leaving. 2 hour delay coming back.

Thu, Apr 19
ORD
OAK
4h 35m
Sat, Apr 21
OAK
ORD
4h 18m
Trip: 3 days
5.6OkayShow reviews
Overall 5.6 Okay
Based on 198 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
ORD
OAK
Good 6.0

Departed on time; arrived on time

Uncomfortable seats; no storage pocket; insufficient tray table

ORD
OAK
Excellent 9.5

Flight on time. Crew very friendly and fun. I knew what to expect.

I'm a grandma but have reasonably decent tech skills. I find Spirit's website a little difficult to maneuver in. I think they are trying to be too "cute" and have lost a little intuitiveness.

ORD
OAK
Good 7.6

Charges for luggage ... people only bring what they need ... one hostess is constantly walking to collect garbage = we are not clean like Koreans

Happy kid was kicking my sit for 4 hours ... licor drinking parents didn't take care ... small price to be part of the village ... kid too young to understand ... maybe not even aware of self

ORD
OAK
Excellent 9.5

Just great! Pay for things you need only.

All good

ORD
OAK
Good 7.6

The flights left on time and arrived earlier than posted time. Flight was very smooth and the Landing was very gentle. airplane to clean.

I understand the get from A to B as cheaply as possible but even the food you order was just limited to snacks. But this is not a deal breaker.

Tue, Apr 24
ORD
OAK
4h 35m
Sat, Apr 28
OAK
ORD
4h 18m
Trip: 5 days
5.6OkayShow reviews
Overall 5.6 Okay
Based on 198 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
ORD
OAK
Okay 4.0

Onboarding was very simple and fast. It took less than 20 minutes

My back was completely messed up from those seats. It was too long a flight to have those hard seats. The pull down tray was also uncomfortable to use for my laptop or not ok.

ORD
OAK
Good 7.6

The flights left on time and arrived earlier than posted time. Flight was very smooth and the Landing was very gentle. airplane to clean.

I understand the get from A to B as cheaply as possible but even the food you order was just limited to snacks. But this is not a deal breaker.

ORD
OAK
Excellent 9.5

Flight on time. Crew very friendly and fun. I knew what to expect.

I'm a grandma but have reasonably decent tech skills. I find Spirit's website a little difficult to maneuver in. I think they are trying to be too "cute" and have lost a little intuitiveness.

ORD
OAK
Good 7.6

Charges for luggage ... people only bring what they need ... one hostess is constantly walking to collect garbage = we are not clean like Koreans

Happy kid was kicking my sit for 4 hours ... licor drinking parents didn't take care ... small price to be part of the village ... kid too young to understand ... maybe not even aware of self

ORD
OAK
Excellent 8.0

Every thing on time all was good.

Tue, Feb 13
ORD
OAK
10h 21m
Wed, Feb 14
OAK
ORD
15h 04m
Trip: 2 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Apr 25
ORD
OAK
4h 35m
Wed, May 2
OAK
ORD
4h 18m
Trip: 8 days
5.6OkayShow reviews
Overall 5.6 Okay
Based on 198 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
ORD
OAK
Good 7.6

The flights left on time and arrived earlier than posted time. Flight was very smooth and the Landing was very gentle. airplane to clean.

I understand the get from A to B as cheaply as possible but even the food you order was just limited to snacks. But this is not a deal breaker.

ORD
OAK
Excellent 8.3

No nonesense, on time, friendly, attentive, dialed in process

Really barebones, no wifi, no reclining, baggage fees seem excessive, no entertainment, USB power would be nice I'd pay $5 each way for that

ORD
OAK
Excellent 9.5

Flight on time. Crew very friendly and fun. I knew what to expect.

I'm a grandma but have reasonably decent tech skills. I find Spirit's website a little difficult to maneuver in. I think they are trying to be too "cute" and have lost a little intuitiveness.

ORD
OAK
Excellent 9.5

Just great! Pay for things you need only.

All good

ORD
OAK
Excellent 8.0

Every thing on time all was good.

Thu, Apr 26
ORD
OAK
4h 35m
Sat, Apr 28
OAK
ORD
4h 18m
Trip: 3 days
5.6OkayShow reviews
Overall 5.6 Okay
Based on 198 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
ORD
OAK
Excellent 8.0

Smooth flights.

15 minute delay leaving. 2 hour delay coming back.

ORD
OAK
Excellent 8.0

Every thing on time all was good.

ORD
OAK
Okay 4.0

Onboarding was very simple and fast. It took less than 20 minutes

My back was completely messed up from those seats. It was too long a flight to have those hard seats. The pull down tray was also uncomfortable to use for my laptop or not ok.

ORD
OAK
Excellent 9.5

Flight on time. Crew very friendly and fun. I knew what to expect.

I'm a grandma but have reasonably decent tech skills. I find Spirit's website a little difficult to maneuver in. I think they are trying to be too "cute" and have lost a little intuitiveness.

ORD
OAK
Excellent 9.5

Just great! Pay for things you need only.

All good

Sun, Jan 7
ORD
OAK
14h 47m
Thu, Jan 11
OAK
ORD
7h 12m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Sat, Apr 28
ORD
OAK
4h 35m
Sun, May 6
OAK
ORD
4h 18m
Trip: 9 days
5.6OkayShow reviews
Overall 5.6 Okay
Based on 198 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
ORD
OAK
Mediocre 2.0

Customer unfriendly

ORD
OAK
Good 6.0

Departed on time; arrived on time

Uncomfortable seats; no storage pocket; insufficient tray table

ORD
OAK
Good 7.6

The flights left on time and arrived earlier than posted time. Flight was very smooth and the Landing was very gentle. airplane to clean.

I understand the get from A to B as cheaply as possible but even the food you order was just limited to snacks. But this is not a deal breaker.

ORD
OAK
Good 6.0

There wasnt any power outlet and wifi

ORD
OAK
Excellent 8.0

Smooth flights.

15 minute delay leaving. 2 hour delay coming back.

Mon, Jan 15
ORD
OAK
15h 57m
Sat, Jan 20
OAK
ORD
10h 40m
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Thu, May 3
ORD
OAK
4h 35m
Sat, May 5
OAK
ORD
4h 18m
Trip: 3 days
5.6OkayShow reviews
Overall 5.6 Okay
Based on 198 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
ORD
OAK
Okay 4.0

Onboarding was very simple and fast. It took less than 20 minutes

My back was completely messed up from those seats. It was too long a flight to have those hard seats. The pull down tray was also uncomfortable to use for my laptop or not ok.

ORD
OAK
Excellent 10.0

Take off wasn't harsh like usually is. Fight attentand was very attentive

ORD
OAK
Excellent 9.5

Flight on time. Crew very friendly and fun. I knew what to expect.

I'm a grandma but have reasonably decent tech skills. I find Spirit's website a little difficult to maneuver in. I think they are trying to be too "cute" and have lost a little intuitiveness.

ORD
OAK
Good 6.0

Departed on time; arrived on time

Uncomfortable seats; no storage pocket; insufficient tray table

ORD
OAK
Excellent 8.3

No nonesense, on time, friendly, attentive, dialed in process

Really barebones, no wifi, no reclining, baggage fees seem excessive, no entertainment, USB power would be nice I'd pay $5 each way for that

Fri, May 4
ORD
OAK
4h 35m
Sun, May 13
OAK
ORD
4h 18m
Trip: 10 days
5.6OkayShow reviews
Overall 5.6 Okay
Based on 198 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
ORD
OAK
Mediocre 2.0

Customer unfriendly

ORD
OAK
Okay 4.0

Onboarding was very simple and fast. It took less than 20 minutes

My back was completely messed up from those seats. It was too long a flight to have those hard seats. The pull down tray was also uncomfortable to use for my laptop or not ok.

ORD
OAK
Good 6.0

Departed on time; arrived on time

Uncomfortable seats; no storage pocket; insufficient tray table

ORD
OAK
Good 7.6

The flights left on time and arrived earlier than posted time. Flight was very smooth and the Landing was very gentle. airplane to clean.

I understand the get from A to B as cheaply as possible but even the food you order was just limited to snacks. But this is not a deal breaker.

ORD
OAK
Good 6.0

There wasnt any power outlet and wifi

Mon, Jan 22
ORD
OAK
10h 21m
Mon, Jan 29
OAK
ORD
10h 00m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Wed, May 9
ORD
OAK
4h 35m
Tue, May 22
OAK
ORD
4h 18m
Trip: 14 days
5.6OkayShow reviews
Overall 5.6 Okay
Based on 198 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
ORD
OAK
Okay 4.0

Onboarding was very simple and fast. It took less than 20 minutes

My back was completely messed up from those seats. It was too long a flight to have those hard seats. The pull down tray was also uncomfortable to use for my laptop or not ok.

ORD
OAK
Good 6.0

There wasnt any power outlet and wifi

ORD
OAK
Excellent 9.5

Flight on time. Crew very friendly and fun. I knew what to expect.

I'm a grandma but have reasonably decent tech skills. I find Spirit's website a little difficult to maneuver in. I think they are trying to be too "cute" and have lost a little intuitiveness.

ORD
OAK
Excellent 8.0

Every thing on time all was good.

ORD
OAK
Good 6.0

Departed on time; arrived on time

Uncomfortable seats; no storage pocket; insufficient tray table

Mon, Feb 12
ORD
OAK
15h 57m
Wed, Feb 21
OAK
ORD
15h 20m
Trip: 10 days
Overall 0.0 Poor
Based on 0 reviews
Thu, May 10
ORD
OAK
4h 35m
Wed, May 16
OAK
ORD
4h 18m
Trip: 7 days
5.6OkayShow reviews
Overall 5.6 Okay
Based on 198 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
ORD
OAK
Good 6.0

There wasnt any power outlet and wifi

ORD
OAK
Excellent 8.0

Smooth flights.

15 minute delay leaving. 2 hour delay coming back.

ORD
OAK
Good 7.6

Charges for luggage ... people only bring what they need ... one hostess is constantly walking to collect garbage = we are not clean like Koreans

Happy kid was kicking my sit for 4 hours ... licor drinking parents didn't take care ... small price to be part of the village ... kid too young to understand ... maybe not even aware of self

ORD
OAK
Excellent 8.0

Every thing on time all was good.

ORD
OAK
Excellent 9.5

Flight on time. Crew very friendly and fun. I knew what to expect.

I'm a grandma but have reasonably decent tech skills. I find Spirit's website a little difficult to maneuver in. I think they are trying to be too "cute" and have lost a little intuitiveness.

Tue, Jan 23
ORD
OAK
15h 29m
Mon, Jan 29
OAK
ORD
10h 00m
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
Fri, May 11
ORD
OAK
4h 35m
Tue, May 15
OAK
ORD
4h 18m
Trip: 5 days
5.6OkayShow reviews
Overall 5.6 Okay
Based on 198 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
ORD
OAK
Okay 4.0

Onboarding was very simple and fast. It took less than 20 minutes

My back was completely messed up from those seats. It was too long a flight to have those hard seats. The pull down tray was also uncomfortable to use for my laptop or not ok.

ORD
OAK
Mediocre 2.0

Customer unfriendly

ORD
OAK
Excellent 9.5

Flight on time. Crew very friendly and fun. I knew what to expect.

I'm a grandma but have reasonably decent tech skills. I find Spirit's website a little difficult to maneuver in. I think they are trying to be too "cute" and have lost a little intuitiveness.

ORD
OAK
Excellent 9.5

Just great! Pay for things you need only.

All good

ORD
OAK
Good 6.0

There wasnt any power outlet and wifi

Show more results
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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.