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Cheap flights from Oakland, California to Chicago from $119

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 3/1. 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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Find the cheapest flights from Oakland, California to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Alaska Airlines Logo
5:17 pm - 2:38 pmOAK-ORD
19h 21m1 stop
Alaska Airlines Logo
8:00 am - 4:23 pmORD-OAK
10h 23m1 stop
$258Alaska Airlines
Find Deal
Fri, Feb 6 - Tue, Feb 10
Delta Logo
12:30 pm - 9:21 pmOAK-ORD
6h 51m1 stop
Delta Logo
7:40 pm - 12:08 amORD-OAK
6h 28m1 stop
$259Delta
Find Deal
Tue, Dec 9 - Tue, Dec 16
Alaska Airlines Logo
6:35 pm - 5:04 amOAK-ORD
8h 29m1 stop
Alaska Airlines Logo
7:45 am - 5:43 pmORD-OAK
11h 58m1 stop
$260Alaska Airlines
Find Deal
Tue, Mar 3 - Wed, Mar 4
Alaska Airlines Logo
6:30 am - 5:04 amOAK-ORD
20h 34m1 stop
Alaska Airlines Logo
6:50 pm - 11:38 pmORD-OAK
30h 48m1 stop
$262Alaska Airlines
Find Deal
Tue, Mar 3 - Wed, Mar 4
Delta Logo
5:55 am - 4:57 pmOAK-ORD
9h 02m2 stops
Delta Logo
7:40 pm - 12:08 amORD-OAK
6h 28m1 stop
$264Delta
Find Deal
Tue, Dec 9 - Tue, Dec 16
Alaska Airlines Logo
2:31 pm - 11:59 pmOAK-ORD
7h 28m1 stop
Alaska Airlines Logo
8:00 am - 2:07 pmORD-OAK
8h 07m1 stop
$268Alaska Airlines
Find Deal
Tue, Dec 16 - Thu, Dec 25
Southwest Logo
5:10 am - 1:30 pmOAK-ORD
6h 20m1 stop
Southwest Logo
2:15 pm - 10:45 pmORD-OAK
10h 30m2 stops
$294Southwest
Find Deal
Fri, Feb 6 - Mon, Feb 9
Southwest Logo
8:55 pm - 1:30 pmOAK-ORD
14h 35m2 stops
Southwest Logo
2:15 pm - 10:45 pmORD-OAK
10h 30m2 stops
$305Southwest
Find Deal
Fri, Feb 6 - Mon, Feb 9
Southwest Logo
5:10 am - 1:30 pmOAK-ORD
6h 20m1 stop
Southwest Logo
7:15 am - 4:45 pmORD-OAK
11h 30m2 stops
$324Southwest
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Sun, Feb 15 - Thu, Feb 19
Southwest Logo
5:25 am - 1:30 pmOAK-ORD
6h 05m1 stop
Southwest Logo
4:25 pm - 9:45 pmORD-OAK
7h 20m1 stop
$329Southwest
Find Deal
Thu, Jan 8 - Tue, Jan 13

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
Feb 6
OAK5:17 pmOakland
19h 21m
1 stop
ORD2:38 pmChicago O'Hare Intl
Feb 10
ORD8:00 amChicago O'Hare Intl
10h 23m
1 stop
OAK4:23 pmOakland
$258
Find similar
Alaska Airlines
Mar 3
OAK6:35 pmOakland
8h 29m
1 stop
ORD5:04 amChicago O'Hare Intl
Mar 4
ORD7:45 amChicago O'Hare Intl
11h 58m
1 stop
OAK5:43 pmOakland
$260
Find similar
Alaska Airlines
Mar 3
OAK6:30 amOakland
20h 34m
1 stop
ORD5:04 amChicago O'Hare Intl
Mar 4
ORD6:50 pmChicago O'Hare Intl
30h 48m
1 stop
OAK11:38 pmOakland
$262
Find similar

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

Our best Southwest deals on Oakland, California to Chicago O'Hare Intl Airport flight tickets
Southwest
Feb 6
OAK5:10 amOakland
6h 20m
1 stop
ORD1:30 pmChicago O'Hare Intl
Feb 9
ORD2:15 pmChicago O'Hare Intl
10h 30m
2 stops
OAK10:45 pmOakland
$294
Find similar
Southwest
Feb 6
OAK8:55 pmOakland
14h 35m
2 stops
ORD1:30 pmChicago O'Hare Intl
Feb 9
ORD2:15 pmChicago O'Hare Intl
10h 30m
2 stops
OAK10:45 pmOakland
$305
Find similar
Southwest
Feb 15
OAK5:10 amOakland
6h 20m
1 stop
ORD1:30 pmChicago O'Hare Intl
Feb 19
ORD7:15 amChicago O'Hare Intl
11h 30m
2 stops
OAK4:45 pmOakland
$324
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 November 6, 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

Fri 2/6

5:17 pm-2:38 pm

1 stop19h 21m

Chicago O'Hare Intl

Tue 2/10

8:00 am-4:23 pm

1 stop10h 23m

$258

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 12/9

12:30 pm-9:21 pm

1 stop6h 51m

Chicago O'Hare Intl

Tue 12/16

7:40 pm-12:08 am

1 stop6h 28m

$259

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 3/3

6:35 pm-5:04 am

1 stop8h 29m

Chicago O'Hare Intl

Wed 3/4

7:45 am-5:43 pm

1 stop11h 58m

$260

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 3/3

6:30 am-5:04 am

1 stop20h 34m

Chicago O'Hare Intl

Wed 3/4

6:50 pm-11:38 pm

1 stop30h 48m

$262

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 12/9

5:55 am-4:57 pm

2 stops9h 02m

Chicago O'Hare Intl

Tue 12/16

7:40 pm-12:08 am

1 stop6h 28m

$264

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 12/16

2:31 pm-11:59 pm

1 stop7h 28m

Chicago O'Hare Intl

Thu 12/25

8:00 am-2:07 pm

1 stop8h 07m

$268

OaklandChicago

OAK - ORD

OAKORD

Oakland

Fri 2/6

5:10 am-1:30 pm

1 stop6h 20m

Chicago O'Hare Intl

Mon 2/9

2:15 pm-10:45 pm

2 stops10h 30m

$294

OaklandChicago

OAK - ORD

OAKORD

Oakland

Fri 2/6

8:55 pm-1:30 pm

2 stops14h 35m

Chicago O'Hare Intl

Mon 2/9

2:15 pm-10:45 pm

2 stops10h 30m

$305

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sun 2/15

5:10 am-1:30 pm

1 stop6h 20m

Chicago O'Hare Intl

Thu 2/19

7:15 am-4:45 pm

2 stops11h 30m

$324

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 1/8

5:25 am-1:30 pm

1 stop6h 05m

Chicago O'Hare Intl

Tue 1/13

4:25 pm-9:45 pm

1 stop7h 20m

$329

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 typical price of a round-trip flight between Oakland, California and Chicago O'Hare Intl Airport?

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 $406. 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 $412 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 November 2025, prices for Oakland, California to Chicago O'Hare Intl Airport flights are approximately 31% more expensive 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
8,122 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $163Free CancellationRating
7.4
9,007 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $189Free CancellationRating
8.0
11,246 reviews
Search Alaska Airlines flights
SouthwestPriceFrom $246Free CancellationRating
8.0
4,241 reviews
Search Southwest flights

  • Southwest Flights From Oakland, California to Chicago O'Hare Intl Airport

    Southwest flies from Oakland, California to Chicago O'Hare Intl Airport around 2 times per week, with 4,240 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Oakland, California to Chicago O'Hare Intl Airport in the last 72 hours was $246 (round-trip), much lower than the average airfare cost of $389 for Southwest flights on this route.

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
Orland Park
Racine
Hammond
Tinley Park
Janesville
Aurora
Elgin
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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