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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 2/24. 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.
Southwest Logo
7:00 am - 3:25 pm
OAK
-
ORD
6h 25m
1 stop
Southwest Logo
4:25 pm - 9:45 pm
ORD
-
OAK
7h 20m
1 stop
$237Southwest
Tue, Feb 17 - Tue, Feb 24
Delta Logo
12:33 pm - 9:35 pm
OAK
-
ORD
7h 02m
1 stop
Delta Logo
7:09 pm - 11:49 pm
ORD
-
OAK
6h 40m
1 stop
$239Delta
Sat, Apr 18 - Wed, Apr 22
Southwest Logo
7:00 am - 3:25 pm
OAK
-
ORD
6h 25m
1 stop
Southwest Logo
1:00 pm - 7:50 pm
ORD
-
OAK
8h 50m
2 stops
$242Southwest
Tue, Feb 17 - Tue, Feb 24
Delta Logo
5:55 am - 3:18 pm
OAK
-
ORD
7h 23m
1 stop
Delta Logo
6:15 am - 4:24 pm
ORD
-
OAK
12h 09m
2 stops
$244Delta
Sat, Apr 11 - Sat, Apr 18
Hawaiian Airlines Logo
6:15 am - 11:56 pm
OAK
-
ORD
15h 41m
1 stop
Hawaiian Airlines Logo
5:29 pm - 11:58 pm
ORD
-
OAK
8h 29m
1 stop
$247Hawaiian Airlines
Sat, Mar 7 - Sat, Mar 14
Alaska Airlines Logo
6:15 am - 4:33 pm
OAK
-
ORD
8h 18m
1 stop
Alaska Airlines Logo
1:00 pm - 10:49 pm
ORD
-
OAK
11h 49m
1 stop
$250Alaska Airlines
Tue, Feb 24 - Thu, Feb 26
Alaska Airlines Logo
2:09 pm - 11:59 pm
OAK
-
ORD
7h 50m
1 stop
Alaska Airlines Logo
7:59 pm - 6:39 pm
ORD
-
OAK
24h 40m
1 stop
$260Alaska Airlines
Wed, Apr 22 - Thu, Apr 30
Alaska Airlines Logo
5:31 pm - 4:33 pm
OAK
-
ORD
21h 02m
1 stop
Alaska Airlines Logo
5:29 pm - 11:54 pm
ORD
-
OAK
8h 25m
1 stop
$263Alaska Airlines
Mon, Mar 2 - Fri, Mar 6
Alaska Airlines Logo
2:09 pm - 11:59 pm
OAK
-
ORD
7h 50m
1 stop
Alaska Airlines Logo
8:50 am - 10:32 pm
ORD
-
OAK
15h 42m
2 stops
$265Alaska Airlines
Sat, Apr 25 - Tue, Apr 28
Southwest Logo
7:00 am - 3:25 pm
OAK
-
ORD
6h 25m
1 stop
Southwest Logo
6:25 pm - 12:10 am
ORD
-
OAK
7h 45m
1 stop
$270Southwest
Tue, Feb 17 - Fri, Feb 20

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 17
OAK7:00 amOakland
6h 25m
1 stop
ORD3:25 pmChicago O'Hare Intl
Feb 24
ORD4:25 pmChicago O'Hare Intl
7h 20m
1 stop
OAK9:45 pmOakland
$237
Southwest
Feb 17
OAK7:00 amOakland
6h 25m
1 stop
ORD3:25 pmChicago O'Hare Intl
Feb 24
ORD1:00 pmChicago O'Hare Intl
8h 50m
2 stops
OAK7:50 pmOakland
$242
Southwest
Feb 17
OAK7:00 amOakland
6h 25m
1 stop
ORD3:25 pmChicago O'Hare Intl
Mar 5
ORD7:20 pmChicago O'Hare Intl
7h 30m
1 stop
OAK12:50 amOakland
$270

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 24
OAK6:15 amOakland
8h 18m
1 stop
ORD4:33 pmChicago O'Hare Intl
Feb 26
ORD1:00 pmChicago O'Hare Intl
11h 49m
1 stop
OAK10:49 pmOakland
$250
Alaska Airlines
Mar 9
OAK6:15 amOakland
29h 58m
1 stop
ORD2:13 pmChicago O'Hare Intl
Mar 11
ORD7:00 amChicago O'Hare Intl
11h 37m
1 stop
OAK4:37 pmOakland
$252
Alaska Airlines
Apr 22
OAK2:09 pmOakland
7h 50m
1 stop
ORD11:59 pmChicago O'Hare Intl
Apr 30
ORD7:59 pmChicago O'Hare Intl
24h 40m
1 stop
OAK6:39 pmOakland
$260

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 January 21, 2026.
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

Tue 2/17

7:00 am-3:25 pm

1 stop6h 25m

Chicago O'Hare Intl

Tue 2/24

4:25 pm-9:45 pm

1 stop7h 20m

$237

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sat 4/18

12:33 pm-9:35 pm

1 stop7h 02m

Chicago O'Hare Intl

Wed 4/22

7:09 pm-11:49 pm

1 stop6h 40m

$239

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 2/17

7:00 am-3:25 pm

1 stop6h 25m

Chicago O'Hare Intl

Tue 2/24

1:00 pm-7:50 pm

2 stops8h 50m

$242

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sat 4/11

5:55 am-3:18 pm

1 stop7h 23m

Chicago O'Hare Intl

Sat 4/18

6:15 am-4:24 pm

2 stops12h 09m

$244

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sat 3/7

6:15 am-11:56 pm

1 stop15h 41m

Chicago O'Hare Intl

Sat 3/14

5:29 pm-11:58 pm

1 stop8h 29m

$247

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 2/24

6:15 am-4:33 pm

1 stop8h 18m

Chicago O'Hare Intl

Thu 2/26

1:00 pm-10:49 pm

1 stop11h 49m

$250

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 4/22

2:09 pm-11:59 pm

1 stop7h 50m

Chicago O'Hare Intl

Thu 4/30

7:59 pm-6:39 pm

1 stop24h 40m

$260

OaklandChicago

OAK - ORD

OAKORD

Oakland

Mon 3/2

5:31 pm-4:33 pm

1 stop21h 02m

Chicago O'Hare Intl

Fri 3/6

5:29 pm-11:54 pm

1 stop8h 25m

$263

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sat 4/25

2:09 pm-11:59 pm

1 stop7h 50m

Chicago O'Hare Intl

Tue 4/28

8:50 am-10:32 pm

2 stops15h 42m

$265

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 2/17

7:00 am-3:25 pm

1 stop6h 25m

Chicago O'Hare Intl

Fri 2/20

6:25 pm-12:10 am

1 stop7h 45m

$270

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 $259.

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 $405. 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 $496.

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 evening is the least expensive time of day to depart. momondo users have found prices as low as $409 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $458. 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 1% 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 January 2026, prices for Oakland, California to Chicago O'Hare Intl Airport flights are approximately 13% 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

Fastest flight time

5h 43m

Direct flights

None
The fastest flight from Oakland, California to Chicago O'Hare Intl Airport takes 5h 43m
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.
Search flight deals

  • 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 5h 43m 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
8,362 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $163Free CancellationRating
7.4
9,190 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $206Free CancellationRating
8.0
11,768 reviews
Search Alaska Airlines flights
SouthwestPriceFrom $246Free CancellationRating
8.0
4,266 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
Schaumburg
South Haven
Rockford
Merrillville
Gurnee
Naperville
Rosemont
New Buffalo
Kenosha
Joliet
Oak Brook
Orland Park
Racine
Hammond
Janesville
Tinley Park
Elgin
Aurora
South Holland

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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