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Cheap flights from Oakland, California to Chicago from $109

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Oakland, California to Chicago departing on 2/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Cheap round-trip flights

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Alaska Airlines Logo
10:30 am - 11:55 pmOAK-ORD
11h 25m2 stops
Alaska Airlines Logo
8:00 am - 4:23 pmORD-OAK
10h 23m1 stop
$298Alaska Airlines
Find Deal
Sat, Jan 17 - Mon, Jan 26
Alaska Airlines Logo
2:49 pm - 12:24 amOAK-ORD
7h 35m1 stop
Alaska Airlines Logo
8:00 am - 1:55 pmORD-OAK
7h 55m1 stop
$299Alaska Airlines
Find Deal
Mon, Nov 17 - Tue, Nov 18
Alaska Airlines Logo
6:30 am - 9:40 pmOAK-ORD
13h 10m1 stop
Alaska Airlines Logo
8:00 am - 1:55 pmORD-OAK
7h 55m1 stop
$302Alaska Airlines
Find Deal
Tue, Nov 11 - Wed, Nov 12
Delta Logo
12:30 pm - 9:21 pmOAK-ORD
6h 51m1 stop
Delta Logo
2:14 pm - 12:08 amORD-OAK
11h 54m2 stops
$316Delta
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Fri, Dec 5 - Sun, Dec 7
Southwest Logo
5:25 am - 1:30 pmOAK-ORD
6h 05m1 stop
Southwest Logo
7:15 am - 1:00 pmORD-OAK
7h 45m1 stop
$319Southwest
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Tue, Nov 11 - Wed, Nov 12
Southwest Logo
12:45 pm - 10:35 pmOAK-ORD
7h 50m2 stops
Southwest Logo
7:15 am - 1:00 pmORD-OAK
7h 45m1 stop
$320Southwest
Find Deal
Tue, Nov 11 - Wed, Nov 12
Delta Logo
4:50 pm - 8:39 amOAK-ORD
13h 49m2 stops
Delta Logo
2:14 pm - 12:08 amORD-OAK
11h 54m2 stops
$321Delta
Find Deal
Fri, Dec 5 - Sun, Dec 7
Southwest Logo
12:45 pm - 10:35 pmOAK-ORD
7h 50m2 stops
Southwest Logo
1:00 pm - 9:20 pmORD-OAK
10h 20m2 stops
$325Southwest
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Tue, Nov 11 - Wed, Nov 12
Delta Logo
12:28 pm - 9:25 pmOAK-ORD
6h 57m1 stop
Delta Logo
5:29 pm - 9:39 pmORD-OAK
6h 10m1 stop
$329Delta
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Sat, Nov 15 - Sat, Nov 22
Southwest Logo
5:25 am - 1:30 pmOAK-ORD
6h 05m1 stop
Southwest Logo
3:05 pm - 11:25 pmORD-OAK
10h 20m1 stop
$331Southwest
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Wed, Dec 10 - Sat, Dec 20

Alaska Airlines flights from Oakland, California to Chicago O'Hare Intl Airport

Our best Alaska Airlines deals on Oakland, California to Chicago O'Hare Intl Airport flight tickets
Alaska Airlines
Jan 17
OAK10:30 amOakland
11h 25m
2 stops
ORD11:55 pmChicago O'Hare Intl
Jan 26
ORD8:00 amChicago O'Hare Intl
10h 23m
1 stop
OAK4:23 pmOakland
$298
Find similar
Alaska Airlines
Nov 17
OAK2:49 pmOakland
7h 35m
1 stop
ORD12:24 amChicago O'Hare Intl
Nov 18
ORD8:00 amChicago O'Hare Intl
7h 55m
1 stop
OAK1:55 pmOakland
$299
Find similar
Alaska Airlines
Nov 11
OAK6:30 amOakland
13h 10m
1 stop
ORD9:40 pmChicago O'Hare Intl
Nov 12
ORD8:00 amChicago O'Hare Intl
7h 55m
1 stop
OAK1:55 pmOakland
$302
Find similar

Delta flights from Oakland, California to Chicago O'Hare Intl Airport

Our best Delta deals on Oakland, California to Chicago O'Hare Intl Airport flight tickets
Delta
Dec 5
OAK12:30 pmOakland
6h 51m
1 stop
ORD9:21 pmChicago O'Hare Intl
Dec 7
ORD2:14 pmChicago O'Hare Intl
11h 54m
2 stops
OAK12:08 amOakland
$316
Find similar
Delta
Dec 5
OAK4:50 pmOakland
13h 49m
2 stops
ORD8:39 amChicago O'Hare Intl
Dec 7
ORD2:14 pmChicago O'Hare Intl
11h 54m
2 stops
OAK12:08 amOakland
$321
Find similar
Delta
Nov 15
OAK12:28 pmOakland
6h 57m
1 stop
ORD9:25 pmChicago O'Hare Intl
Nov 22
ORD5:29 pmChicago O'Hare Intl
6h 10m
1 stop
OAK9:39 pmOakland
$329
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Oakland, California to Chicago O'Hare Intl Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated October 19, 2025.
Use the filters below to find and compare flights from Oakland, California to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sat 1/17

10:30 am-11:55 pm

2 stops11h 25m

Chicago O'Hare Intl

Mon 1/26

8:00 am-4:23 pm

1 stop10h 23m

$298

OaklandChicago

OAK - ORD

OAKORD

Oakland

Mon 11/17

2:49 pm-12:24 am

1 stop7h 35m

Chicago O'Hare Intl

Tue 11/18

8:00 am-1:55 pm

1 stop7h 55m

$299

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 11/11

6:30 am-9:40 pm

1 stop13h 10m

Chicago O'Hare Intl

Wed 11/12

8:00 am-1:55 pm

1 stop7h 55m

$302

OaklandChicago

OAK - ORD

OAKORD

Oakland

Fri 12/5

12:30 pm-9:21 pm

1 stop6h 51m

Chicago O'Hare Intl

Sun 12/7

2:14 pm-12:08 am

2 stops11h 54m

$316

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 11/11

5:25 am-1:30 pm

1 stop6h 05m

Chicago O'Hare Intl

Wed 11/12

7:15 am-1:00 pm

1 stop7h 45m

$319

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 11/11

12:45 pm-10:35 pm

2 stops7h 50m

Chicago O'Hare Intl

Wed 11/12

7:15 am-1:00 pm

1 stop7h 45m

$320

OaklandChicago

OAK - ORD

OAKORD

Oakland

Fri 12/5

4:50 pm-8:39 am

2 stops13h 49m

Chicago O'Hare Intl

Sun 12/7

2:14 pm-12:08 am

2 stops11h 54m

$321

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 11/11

12:45 pm-10:35 pm

2 stops7h 50m

Chicago O'Hare Intl

Wed 11/12

1:00 pm-9:20 pm

2 stops10h 20m

$325

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sat 11/15

12:28 pm-9:25 pm

1 stop6h 57m

Chicago O'Hare Intl

Sat 11/22

5:29 pm-9:39 pm

1 stop6h 10m

$329

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 12/10

5:25 am-1:30 pm

1 stop6h 05m

Chicago O'Hare Intl

Sat 12/20

3:05 pm-11:25 pm

1 stop10h 20m

$331

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Oakland, California to Chicago O'Hare Intl Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

The month of July is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Oakland, California averaging around $232.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Wednesday when prices can be found for as low as $403. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Oakland, California because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $505.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Oakland, California in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $411 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $466. Of course, these prices can vary depending on the time of year and what airport you fly to.

Can stopping save me money on Oakland, California to Chicago O'Hare Intl Airport flights?

You could potentially save up to 2% on your flight if you consider stops on a Oakland, California to Chicago O'Hare Intl Airport flight.

How have Oakland, California to Chicago O'Hare Intl Airport flight prices changed over time?

As of October 2025, prices for Oakland, California to Chicago O'Hare Intl Airport flights are approximately 10% cheaper when compared to flights at the same time last year.

When to book flights from Oakland, California to Chicago O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Oakland, California to Chicago O'Hare Intl Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Oakland, California to Chicago O'Hare Intl Airport (OAK to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Oakland, California to Chicago O'Hare Intl Airport

Direct flights

None
There are no direct flights from Oakland, California to Chicago O'Hare Intl Airport. There are no popular flight routes from Oakland, California to Chicago O'Hare Intl Airport.
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  • How far is Oakland to Chicago O'Hare Intl by plane?

    The distance between Oakland and Chicago O'Hare Intl is about 1830.7 mi. Typically, this will take 6h 05m by plane in normal conditions.

  • When did momondo last update prices for flights from Oakland Airport to Chicago O'Hare Intl Airport?

    Prices for flights from Oakland Airport to Chicago O'Hare Intl Airport refresh daily.

  • How many operators does momondo search for flights from Oakland Airport to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from Oakland Airport to Chicago O'Hare Intl Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Oakland Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The travel and health documents required for your trip to Chicago O'Hare Intl Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago O'Hare Intl Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular airline from Oakland, California to Chicago O'Hare Intl Airport?

Best airlines flying from Oakland, California to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Oakland, California to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $108Free CancellationRating
6.3
8,101 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $163Free CancellationRating
7.4
8,993 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $189Free CancellationRating
8.0
11,134 reviews
Search Alaska Airlines flights
SouthwestPriceFrom $246Free CancellationRating
8.0
4,241 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
South Haven
Schaumburg
Rockford
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Racine
Orland Park
Hammond
Tinley Park
Janesville
Elgin
Aurora
Benton Harbor

Why use momondo?

Why should I use momondo to find a flight deal from Oakland to Chicago?

It is quick and easy to find Oakland to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Oakland to Chicago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Oakland to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from Oakland to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Oakland to Chicago.

I’m not ready to book a flight from Oakland to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Oakland to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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