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Cheap flights from Oakland, California to Chicago from $137

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 6/23. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
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
5:35 pm - 5:00 am
OAK
-
ORD
9h 25m
1 stop
Alaska Airlines Logo
6:20 am - 2:10 pm
ORD
-
OAK
9h 50m
1 stop
$349Alaska Airlines
Tue, Jul 14 - Wed, Jul 15
Delta Logo
6:00 am - 8:55 pm
OAK
-
ORD
12h 55m
2 stops
Delta Logo
12:40 pm - 11:59 pm
ORD
-
OAK
13h 19m
2 stops
$350Delta
Tue, Sep 22 - Fri, Sep 25
Delta Logo
6:00 am - 4:17 pm
OAK
-
ORD
8h 17m
2 stops
Delta Logo
5:00 pm - 11:49 pm
ORD
-
OAK
8h 49m
1 stop
$352Delta
Sun, Sep 6 - Sat, Sep 12
Delta Logo
12:29 pm - 9:47 pm
OAK
-
ORD
7h 18m
1 stop
Delta Logo
7:40 pm - 11:59 pm
ORD
-
OAK
6h 19m
1 stop
$354Delta
Fri, Sep 25 - Mon, Sep 28
Alaska Airlines Logo
2:50 pm - 11:36 pm
OAK
-
ORD
6h 46m
1 stop
Alaska Airlines Logo
6:20 am - 2:10 pm
ORD
-
OAK
9h 50m
1 stop
$355Alaska Airlines
Thu, Jul 16 - Wed, Jul 29
Delta Logo
6:00 am - 4:17 pm
OAK
-
ORD
8h 17m
2 stops
Delta Logo
9:30 am - 4:31 pm
ORD
-
OAK
9h 01m
2 stops
$357Delta
Sun, Sep 6 - Sat, Sep 12
Alaska Airlines Logo
3:13 pm - 11:59 pm
OAK
-
ORD
6h 46m
1 stop
Alaska Airlines Logo
7:59 pm - 11:06 am
ORD
-
OAK
17h 07m
1 stop
$358Alaska Airlines
Thu, Sep 10 - Sun, Sep 13
Delta Logo
6:00 am - 5:23 pm
OAK
-
ORD
9h 23m
2 stops
Delta Logo
7:40 pm - 11:59 pm
ORD
-
OAK
6h 19m
1 stop
$359Delta
Wed, Sep 30 - Fri, Oct 2
Delta Logo
6:00 am - 4:23 pm
OAK
-
ORD
8h 23m
2 stops
Delta Logo
7:40 pm - 11:50 pm
ORD
-
OAK
6h 10m
1 stop
$360Delta
Tue, Jul 14 - Tue, Jul 28
Alaska Airlines Logo
7:52 am - 5:00 am
OAK
-
ORD
19h 08m
1 stop
Alaska Airlines Logo
8:20 pm - 11:21 am
ORD
-
OAK
17h 01m
2 stops
$362Alaska Airlines
Wed, Jul 1 - Tue, Jul 7

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
Jul 14
OAK5:35 pmOakland
9h 25m
1 stop
ORD5:00 amChicago O'Hare Intl
Jul 15
ORD6:20 amChicago O'Hare Intl
9h 50m
1 stop
OAK2:10 pmOakland
$349
Alaska Airlines
Jul 16
OAK2:50 pmOakland
6h 46m
1 stop
ORD11:36 pmChicago O'Hare Intl
Jul 29
ORD6:20 amChicago O'Hare Intl
9h 50m
1 stop
OAK2:10 pmOakland
$355
Alaska Airlines
Sep 10
OAK3:13 pmOakland
6h 46m
1 stop
ORD11:59 pmChicago O'Hare Intl
Sep 13
ORD7:59 pmChicago O'Hare Intl
17h 07m
1 stop
OAK11:06 amOakland
$358

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
Sep 22
OAK6:00 amOakland
12h 55m
2 stops
ORD8:55 pmChicago O'Hare Intl
Sep 25
ORD12:40 pmChicago O'Hare Intl
13h 19m
2 stops
OAK11:59 pmOakland
$350
Delta
Sep 6
OAK6:00 amOakland
8h 17m
2 stops
ORD4:17 pmChicago O'Hare Intl
Sep 12
ORD5:00 pmChicago O'Hare Intl
8h 49m
1 stop
OAK11:49 pmOakland
$352
Delta
Sep 25
OAK12:29 pmOakland
7h 18m
1 stop
ORD9:47 pmChicago O'Hare Intl
Sep 28
ORD7:40 pmChicago O'Hare Intl
6h 19m
1 stop
OAK11:59 pmOakland
$354

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 May 29, 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

Cheapest round-trip

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 7/14

5:35 pm-5:00 am

1 stop9h 25m

Chicago O'Hare Intl

Wed 7/15

6:20 am-2:10 pm

1 stop9h 50m

$349

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 9/22

6:00 am-8:55 pm

2 stops12h 55m

Chicago O'Hare Intl

Fri 9/25

12:40 pm-11:59 pm

2 stops13h 19m

$350

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sun 9/6

6:00 am-4:17 pm

2 stops8h 17m

Chicago O'Hare Intl

Sat 9/12

5:00 pm-11:49 pm

1 stop8h 49m

$352
Quickest round-trip

OaklandChicago

OAK - ORD

OAKORD

Oakland

Fri 9/25

12:29 pm-9:47 pm

1 stop7h 18m

Chicago O'Hare Intl

Mon 9/28

7:40 pm-11:59 pm

1 stop6h 19m

$354

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 7/16

2:50 pm-11:36 pm

1 stop6h 46m

Chicago O'Hare Intl

Wed 7/29

6:20 am-2:10 pm

1 stop9h 50m

$355

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sun 9/6

6:00 am-4:17 pm

2 stops8h 17m

Chicago O'Hare Intl

Sat 9/12

9:30 am-4:31 pm

2 stops9h 01m

$357

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 9/10

3:13 pm-11:59 pm

1 stop6h 46m

Chicago O'Hare Intl

Sun 9/13

7:59 pm-11:06 am

1 stop17h 07m

$358

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 9/30

6:00 am-5:23 pm

2 stops9h 23m

Chicago O'Hare Intl

Fri 10/2

7:40 pm-11:59 pm

1 stop6h 19m

$359

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 7/14

6:00 am-4:23 pm

2 stops8h 23m

Chicago O'Hare Intl

Tue 7/28

7:40 pm-11:50 pm

1 stop6h 10m

$360

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 7/1

7:52 am-5:00 am

1 stop19h 08m

Chicago O'Hare Intl

Tue 7/7

8:20 pm-11:21 am

2 stops17h 01m

$362

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 August is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Oakland, California averaging around $349.

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 $434. 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 $546.

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 $443 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $481. 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 26% 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?

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

6h 10m

Direct flights

None
The fastest flight from Oakland, California to Chicago O'Hare Intl Airport takes 6h 10m
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

Frequently asked questions about flying from Oakland, California to Chicago O'Hare Intl Airport

  • 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 10m 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 $97Free CancellationRating
6.2
Search Spirit Airlines flights
United AirlinesPriceFrom $207Free CancellationRating
7.4
9,766 reviews
Search United Airlines flights
SouthwestPriceFrom $252Free CancellationRating
8.0
4,265 reviews
Search Southwest flights
Alaska AirlinesPriceFrom $260Free CancellationRating
7.9
12,433 reviews
Search Alaska Airlines 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
Rosemont
Naperville
Orland Park
New Buffalo
Oak Brook
Kenosha
Joliet
Aurora
Racine
Janesville
Hammond
Evanston
Tinley Park
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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