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

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Sat 12/16
Sat 12/23
Any month
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Good to Know

Low Season:
October
Best time to beat the crowds
3%
expected price decrease
High Season:
December
Most popular time to fly
23%
expected price increase
Average Price:
$406
(avg. price over the last 2 weeks)
Good Deal:
$406
or less (round trip)

When to Book Flights from Oakland to Chicago

Average price per month
Flight prices as travel date approaches
-1 day
-2 days

Top tips for Finding a Cheap Flight

The cheapest flight from Oakland to Chicago was found 53 days before departure, on average.
Book at least 2 weeks before departure in order to get a below-average price.
Morning departure is around 6% cheaper 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 Flights

How long does a flight from Oakland to Chicago take?
An average nonstop flight takes 4h 18m, covering a distance of 1846 miles.
How many flights are there between Oakland and Chicago?
There are 56 (nonstop) flights between Oakland and Chicago per week, averaging 8 per day.
Which airlines provide the cheapest flights from Oakland to Chicago?
In the past 3 days, the cheapest round-trip tickets were found on Spirit Airlines ($141) and Multiple Airlines ($163)
Do I need a passport to fly between Oakland and Chicago?
No.
Which airlines fly most frequently between Oakland and Chicago?
Southwest (8 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly Oakland to Chicago?
For Oakland to Chicago, Saturday is the cheapest day to fly on average and Monday is the most expensive. Flying from Chicago back to Oakland, the best deals are generally found on Tuesday, with Wednesday being the most expensive.

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

Airports
Origin
Oakland
$141
only
$141
Destination
Chicago
$141
only
$141
Sat, Apr 14
OAK
ORD
4h 18m
Sat, Apr 21
ORD
OAK
4h 35m
Trip: 8 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 188 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
OAK
ORD
Excellent 8.0

First time I have flown with Spirit - had to get used to new rules. Everything went smoothly- still a few things that aren't clear.

If we are given a cost gradient for seating, why not do it for drinks and food. Sell a few outstanding spirits, food, beverages etc- customers will either want to pay extra or not.

OAK
ORD
Excellent 10.0

Everything was fast and easy

Having to pay 55 dollars for 1 bag being over weight

OAK
ORD
Good 7.5

Punctuality

Small tray tables

OAK
ORD
Mediocre 3.3

Flight was on time for boarding and arrived early at destination.

Zero snacks, had to pay $16 to just sit down, had to pay $49 for a CARRYON. Ended up being approximately the same price as flying a better Airline.

OAK
ORD
Good 6.0

The short tray tables didn't allow me to put my laptop on them.

Thu, Jan 18
OAK
ORD
10h 40m
Wed, Jan 24
ORD
OAK
27h 53m
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Apr 18
OAK
ORD
4h 18m
Wed, Apr 25
ORD
OAK
4h 35m
Trip: 8 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 188 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
OAK
ORD
Okay 5.3

I didn't pay the lowest amount on this lowest of budget airlines (still upset I couldn't change my fair when I saw a flash sale a week after purchase). Comfortable because I paid to upgrade seats so no one [else] would be tortured physically by my toddler!

Surly flight attendant should get another job, she was short with every passenger. All food AND drinks are sold on flight, no complimentary ANYTHING, which is not convenient given long flights and airport security but we got what we paid for which is a ride to our destination...oh yeah, 45 minute delay due to missing paperwork :,(, time made up in air but we sat for 45 minutes. Knowing the real delay time would have been nice so I could return to terminal to get food.

OAK
ORD
Good 7.0

Very short lines for security and boarding. Extremely efficient

Seating legroom was limited. I'm only 5'7 and found legroom limited.

OAK
ORD
Good 6.5

The crew was nice

Cheap flight with no amenities. Everything cost extra and more than other major airlines. Planes are small and seats are cramped. No wifi. This was my first and last time with Spirit Airlines. Buyer beware! Pay for luggage online before your flight to save money! I first paid $52 compared to $30 something online.

OAK
ORD
Good 6.0

The short tray tables didn't allow me to put my laptop on them.

OAK
ORD
Excellent 10.0

Everything was fast and easy

Having to pay 55 dollars for 1 bag being over weight

Wed, Apr 25
OAK
ORD
4h 18m
Sat, Apr 28
ORD
OAK
4h 35m
Trip: 4 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 188 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
OAK
ORD
Mediocre 2.0

0

1. Baggage charge expensive! over paid extra fee for $65.00 compared to other airlines only for $25.00; was not aware of hidden fees! 2. Fight attendant, (white woman, tall, large woman, dark hair) was very rude to me. While giving flight demonstration she said, "you need to turn that off" (referring to my cell phone). Then she said it the second time, very rudely "TURN IT OFF!!!" This is very unprofessional, this is not acceptable. I had my music off and was listening to her in the first place! Her facial expression and tone of voice was very degrading and racist.

OAK
ORD
Good 7.0

Very short lines for security and boarding. Extremely efficient

Seating legroom was limited. I'm only 5'7 and found legroom limited.

OAK
ORD
Okay 4.0

price of flight

over 2 hour delay in departure time; uncomfortable seats. tiny tray table, charge for water

OAK
ORD
Good 7.5

Punctuality

Small tray tables

OAK
ORD
Good 6.5

The crew was nice

Cheap flight with no amenities. Everything cost extra and more than other major airlines. Planes are small and seats are cramped. No wifi. This was my first and last time with Spirit Airlines. Buyer beware! Pay for luggage online before your flight to save money! I first paid $52 compared to $30 something online.

Tue, May 1
OAK
ORD
4h 18m
Thu, May 10
ORD
OAK
4h 35m
Trip: 10 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 188 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
OAK
ORD
Okay 4.0

price of flight

over 2 hour delay in departure time; uncomfortable seats. tiny tray table, charge for water

OAK
ORD
Excellent 10.0

Everything was fast and easy

Having to pay 55 dollars for 1 bag being over weight

OAK
ORD
Good 6.0

Easy check in and friendly staff

Seats were very uncomfortable

OAK
ORD
Good 6.5

The crew was nice

Cheap flight with no amenities. Everything cost extra and more than other major airlines. Planes are small and seats are cramped. No wifi. This was my first and last time with Spirit Airlines. Buyer beware! Pay for luggage online before your flight to save money! I first paid $52 compared to $30 something online.

OAK
ORD
Excellent 8.0

The seats are not very comfortable

Mon, Jan 29
OAK
ORD
11h 49m
Tue, Jan 30
ORD
OAK
15h 29m
Trip: 2 days
Overall 0.0 Poor
Based on 0 reviews
Sat, May 5
OAK
ORD
4h 18m
Tue, May 8
ORD
OAK
4h 35m
Trip: 4 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 188 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
OAK
ORD
Okay 4.0

price of flight

over 2 hour delay in departure time; uncomfortable seats. tiny tray table, charge for water

OAK
ORD
Mediocre 2.0

0

1. Baggage charge expensive! over paid extra fee for $65.00 compared to other airlines only for $25.00; was not aware of hidden fees! 2. Fight attendant, (white woman, tall, large woman, dark hair) was very rude to me. While giving flight demonstration she said, "you need to turn that off" (referring to my cell phone). Then she said it the second time, very rudely "TURN IT OFF!!!" This is very unprofessional, this is not acceptable. I had my music off and was listening to her in the first place! Her facial expression and tone of voice was very degrading and racist.

OAK
ORD
Good 7.5

Punctuality

Small tray tables

OAK
ORD
Excellent 8.0

The seats are not very comfortable

OAK
ORD
Excellent 10.0

Everything was fast and easy

Having to pay 55 dollars for 1 bag being over weight

Mon, Feb 5
OAK
ORD
9h 55m
Wed, Feb 7
ORD
OAK
15h 29m
Trip: 3 days
Overall 0.0 Poor
Based on 0 reviews
Sun, May 6
OAK
ORD
4h 18m
Tue, May 8
ORD
OAK
4h 35m
Trip: 3 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 188 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
OAK
ORD
Excellent 8.0

First time I have flown with Spirit - had to get used to new rules. Everything went smoothly- still a few things that aren't clear.

If we are given a cost gradient for seating, why not do it for drinks and food. Sell a few outstanding spirits, food, beverages etc- customers will either want to pay extra or not.

OAK
ORD
Good 7.5

Punctuality

Small tray tables

OAK
ORD
Mediocre 2.0

0

1. Baggage charge expensive! over paid extra fee for $65.00 compared to other airlines only for $25.00; was not aware of hidden fees! 2. Fight attendant, (white woman, tall, large woman, dark hair) was very rude to me. While giving flight demonstration she said, "you need to turn that off" (referring to my cell phone). Then she said it the second time, very rudely "TURN IT OFF!!!" This is very unprofessional, this is not acceptable. I had my music off and was listening to her in the first place! Her facial expression and tone of voice was very degrading and racist.

OAK
ORD
Good 6.5

The crew was nice

Cheap flight with no amenities. Everything cost extra and more than other major airlines. Planes are small and seats are cramped. No wifi. This was my first and last time with Spirit Airlines. Buyer beware! Pay for luggage online before your flight to save money! I first paid $52 compared to $30 something online.

OAK
ORD
Okay 5.3

I didn't pay the lowest amount on this lowest of budget airlines (still upset I couldn't change my fair when I saw a flash sale a week after purchase). Comfortable because I paid to upgrade seats so no one [else] would be tortured physically by my toddler!

Surly flight attendant should get another job, she was short with every passenger. All food AND drinks are sold on flight, no complimentary ANYTHING, which is not convenient given long flights and airport security but we got what we paid for which is a ride to our destination...oh yeah, 45 minute delay due to missing paperwork :,(, time made up in air but we sat for 45 minutes. Knowing the real delay time would have been nice so I could return to terminal to get food.

Wed, Jan 24
OAK
ORD
6h 12m
Mon, Jan 29
ORD
OAK
9h 11m
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Tue, May 8
OAK
ORD
4h 18m
Thu, May 10
ORD
OAK
4h 35m
Trip: 3 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 188 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
OAK
ORD
Mediocre 2.0

0

1. Baggage charge expensive! over paid extra fee for $65.00 compared to other airlines only for $25.00; was not aware of hidden fees! 2. Fight attendant, (white woman, tall, large woman, dark hair) was very rude to me. While giving flight demonstration she said, "you need to turn that off" (referring to my cell phone). Then she said it the second time, very rudely "TURN IT OFF!!!" This is very unprofessional, this is not acceptable. I had my music off and was listening to her in the first place! Her facial expression and tone of voice was very degrading and racist.

OAK
ORD
Mediocre 3.3

Flight was on time for boarding and arrived early at destination.

Zero snacks, had to pay $16 to just sit down, had to pay $49 for a CARRYON. Ended up being approximately the same price as flying a better Airline.

OAK
ORD
Good 6.0

Easy check in and friendly staff

Seats were very uncomfortable

OAK
ORD
Excellent 8.0

The seats are not very comfortable

OAK
ORD
Good 6.5

The crew was nice

Cheap flight with no amenities. Everything cost extra and more than other major airlines. Planes are small and seats are cramped. No wifi. This was my first and last time with Spirit Airlines. Buyer beware! Pay for luggage online before your flight to save money! I first paid $52 compared to $30 something online.

Thu, Jan 25
OAK
ORD
6h 12m
Mon, Jan 29
ORD
OAK
9h 11m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Tue, May 15
OAK
ORD
4h 18m
Tue, May 22
ORD
OAK
4h 35m
Trip: 8 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 188 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
OAK
ORD
Okay 5.3

I didn't pay the lowest amount on this lowest of budget airlines (still upset I couldn't change my fair when I saw a flash sale a week after purchase). Comfortable because I paid to upgrade seats so no one [else] would be tortured physically by my toddler!

Surly flight attendant should get another job, she was short with every passenger. All food AND drinks are sold on flight, no complimentary ANYTHING, which is not convenient given long flights and airport security but we got what we paid for which is a ride to our destination...oh yeah, 45 minute delay due to missing paperwork :,(, time made up in air but we sat for 45 minutes. Knowing the real delay time would have been nice so I could return to terminal to get food.

OAK
ORD
Excellent 8.0

The seats are not very comfortable

OAK
ORD
Excellent 10.0

Everything was fast and easy

Having to pay 55 dollars for 1 bag being over weight

OAK
ORD
Good 6.0

Easy check in and friendly staff

Seats were very uncomfortable

OAK
ORD
Mediocre 2.0

0

1. Baggage charge expensive! over paid extra fee for $65.00 compared to other airlines only for $25.00; was not aware of hidden fees! 2. Fight attendant, (white woman, tall, large woman, dark hair) was very rude to me. While giving flight demonstration she said, "you need to turn that off" (referring to my cell phone). Then she said it the second time, very rudely "TURN IT OFF!!!" This is very unprofessional, this is not acceptable. I had my music off and was listening to her in the first place! Her facial expression and tone of voice was very degrading and racist.

Wed, Jan 24
OAK
ORD
6h 12m
Mon, Jan 29
ORD
OAK
9h 11m
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Wed, May 16
OAK
ORD
4h 18m
Tue, May 22
ORD
OAK
4h 35m
Trip: 7 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 188 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
OAK
ORD
Excellent 8.0

The seats are not very comfortable

OAK
ORD
Mediocre 3.3

Flight was on time for boarding and arrived early at destination.

Zero snacks, had to pay $16 to just sit down, had to pay $49 for a CARRYON. Ended up being approximately the same price as flying a better Airline.

OAK
ORD
Excellent 8.0

First time I have flown with Spirit - had to get used to new rules. Everything went smoothly- still a few things that aren't clear.

If we are given a cost gradient for seating, why not do it for drinks and food. Sell a few outstanding spirits, food, beverages etc- customers will either want to pay extra or not.

OAK
ORD
Okay 4.0

price of flight

over 2 hour delay in departure time; uncomfortable seats. tiny tray table, charge for water

OAK
ORD
Good 7.0

Very short lines for security and boarding. Extremely efficient

Seating legroom was limited. I'm only 5'7 and found legroom limited.

Thu, Jan 25
OAK
ORD
6h 12m
Mon, Jan 29
ORD
OAK
9h 11m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Tue, May 22
OAK
ORD
4h 18m
Wed, May 23
ORD
OAK
4h 35m
Trip: 2 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 188 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
OAK
ORD
Good 7.0

Very short lines for security and boarding. Extremely efficient

Seating legroom was limited. I'm only 5'7 and found legroom limited.

OAK
ORD
Okay 4.0

price of flight

over 2 hour delay in departure time; uncomfortable seats. tiny tray table, charge for water

OAK
ORD
Excellent 8.0

The seats are not very comfortable

OAK
ORD
Mediocre 2.0

0

1. Baggage charge expensive! over paid extra fee for $65.00 compared to other airlines only for $25.00; was not aware of hidden fees! 2. Fight attendant, (white woman, tall, large woman, dark hair) was very rude to me. While giving flight demonstration she said, "you need to turn that off" (referring to my cell phone). Then she said it the second time, very rudely "TURN IT OFF!!!" This is very unprofessional, this is not acceptable. I had my music off and was listening to her in the first place! Her facial expression and tone of voice was very degrading and racist.

OAK
ORD
Good 7.5

Punctuality

Small tray tables

Tue, Jun 5
OAK
ORD
4h 18m
Wed, Jun 13
ORD
OAK
4h 35m
Trip: 9 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 188 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
OAK
ORD
Excellent 8.0

First time I have flown with Spirit - had to get used to new rules. Everything went smoothly- still a few things that aren't clear.

If we are given a cost gradient for seating, why not do it for drinks and food. Sell a few outstanding spirits, food, beverages etc- customers will either want to pay extra or not.

OAK
ORD
Good 7.5

Punctuality

Small tray tables

OAK
ORD
Okay 5.3

I didn't pay the lowest amount on this lowest of budget airlines (still upset I couldn't change my fair when I saw a flash sale a week after purchase). Comfortable because I paid to upgrade seats so no one [else] would be tortured physically by my toddler!

Surly flight attendant should get another job, she was short with every passenger. All food AND drinks are sold on flight, no complimentary ANYTHING, which is not convenient given long flights and airport security but we got what we paid for which is a ride to our destination...oh yeah, 45 minute delay due to missing paperwork :,(, time made up in air but we sat for 45 minutes. Knowing the real delay time would have been nice so I could return to terminal to get food.

OAK
ORD
Okay 4.0

price of flight

over 2 hour delay in departure time; uncomfortable seats. tiny tray table, charge for water

OAK
ORD
Mediocre 3.3

Flight was on time for boarding and arrived early at destination.

Zero snacks, had to pay $16 to just sit down, had to pay $49 for a CARRYON. Ended up being approximately the same price as flying a better Airline.

Mon, Feb 5
OAK
ORD
9h 55m
Sun, Feb 11
ORD
OAK
15h 29m
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Jun 6
OAK
ORD
4h 18m
Wed, Jun 13
ORD
OAK
4h 35m
Trip: 8 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 188 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
OAK
ORD
Excellent 8.0

The seats are not very comfortable

OAK
ORD
Mediocre 3.3

Flight was on time for boarding and arrived early at destination.

Zero snacks, had to pay $16 to just sit down, had to pay $49 for a CARRYON. Ended up being approximately the same price as flying a better Airline.

OAK
ORD
Good 7.5

Punctuality

Small tray tables

OAK
ORD
Good 6.5

The crew was nice

Cheap flight with no amenities. Everything cost extra and more than other major airlines. Planes are small and seats are cramped. No wifi. This was my first and last time with Spirit Airlines. Buyer beware! Pay for luggage online before your flight to save money! I first paid $52 compared to $30 something online.

OAK
ORD
Mediocre 2.0

0

1. Baggage charge expensive! over paid extra fee for $65.00 compared to other airlines only for $25.00; was not aware of hidden fees! 2. Fight attendant, (white woman, tall, large woman, dark hair) was very rude to me. While giving flight demonstration she said, "you need to turn that off" (referring to my cell phone). Then she said it the second time, very rudely "TURN IT OFF!!!" This is very unprofessional, this is not acceptable. I had my music off and was listening to her in the first place! Her facial expression and tone of voice was very degrading and racist.

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Prices are per person and are for e–tickets and include all taxes & fees in USD.

We attempt to get accurate prices, however, prices are not guaranteed.

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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.