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Cheap flights from Oakland, California to Chicago from $93

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 9/30. 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

Logo
6:30 am - 9:32 pmOAK-ORD
13h 02m1 stop
Logo
8:49 pm - 11:32 pmORD-OAK
28h 43m2 stops
$255
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Thu, Sep 25 - Sun, Sep 28
Southwest Logo
3:25 pm - 11:05 pmOAK-ORD
5h 40m1 stop
Southwest Logo
12:40 pm - 7:45 pmORD-OAK
9h 05m2 stops
$256Southwest
Find Deal
Sat, Oct 18 - Tue, Oct 21
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
$261Alaska Airlines
Find Deal
Thu, Nov 13 - Tue, Nov 18
Alaska Airlines Logo
7:12 pm - 5:01 amOAK-ORD
7h 49m1 stop
Alaska Airlines Logo
2:05 pm - 11:59 pmORD-OAK
11h 54m2 stops
$262Alaska Airlines
Find Deal
Fri, Nov 14 - Mon, Nov 17
Spirit Airlines Logo
6:30 am - 4:59 pmOAK-ORD
8h 29m1 stop
Spirit Airlines Logo
6:05 pm - 11:32 pmORD-OAK
7h 27m1 stop
$266Spirit Airlines
Find Deal
Fri, Sep 26 - Mon, Sep 29
Spirit Airlines Logo
6:30 am - 9:32 pmOAK-ORD
13h 02m1 stop
Spirit Airlines Logo
6:05 pm - 11:32 pmORD-OAK
7h 27m1 stop
$267Spirit Airlines
Find Deal
Sat, Sep 27 - Mon, Sep 29
Hawaiian Airlines Logo
8:03 pm - 6:22 amOAK-ORD
8h 19m1 stop
Hawaiian Airlines Logo
3:25 pm - 11:59 pmORD-OAK
10h 34m1 stop
$276Hawaiian Airlines
Find Deal
Fri, Oct 31 - Tue, Nov 4
Delta Logo
5:45 am - 4:28 pmOAK-ORD
8h 43m2 stops
Delta Logo
7:40 pm - 12:03 amORD-OAK
6h 23m1 stop
$282Delta
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Sat, Nov 15 - Mon, Nov 17
Delta Logo
5:45 am - 6:26 pmOAK-ORD
10h 41m2 stops
Delta Logo
2:30 pm - 9:39 pmORD-OAK
9h 09m2 stops
$287Delta
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Sun, Nov 9 - Sat, Nov 15
Hawaiian Airlines Logo
8:05 pm - 6:24 amOAK-ORD
8h 19m1 stop
Hawaiian Airlines Logo
5:59 pm - 12:03 amORD-OAK
8h 04m1 stop
$316Hawaiian Airlines
Find Deal
Sat, Oct 4 - Sat, Oct 11

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

Our best Hawaiian Airlines deals on Oakland, California to Chicago O'Hare Intl Airport flight tickets
Hawaiian Airlines
Oct 31
OAK8:03 pmOakland
8h 19m
1 stop
ORD6:22 amChicago O'Hare Intl
Nov 4
ORD3:25 pmChicago O'Hare Intl
10h 34m
1 stop
OAK11:59 pmOakland
$276
Find similar
Hawaiian Airlines
Oct 4
OAK8:05 pmOakland
8h 19m
1 stop
ORD6:24 amChicago O'Hare Intl
Oct 11
ORD5:59 pmChicago O'Hare Intl
8h 04m
1 stop
OAK12:03 amOakland
$316
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
Oct 18
OAK3:25 pmOakland
5h 40m
1 stop
ORD11:05 pmChicago O'Hare Intl
Oct 21
ORD12:40 pmChicago O'Hare Intl
9h 05m
2 stops
OAK7:45 pmOakland
$256
Find similar
Southwest
Oct 3
OAK5:35 amOakland
6h 25m
1 stop
ORD2:00 pmChicago O'Hare Intl
Oct 7
ORD7:00 amChicago O'Hare Intl
9h 30m
2 stops
OAK2:30 pmOakland
$270
Find similar
Southwest
Oct 30
OAK5:35 amOakland
6h 25m
1 stop
ORD2:00 pmChicago O'Hare Intl
Nov 2
ORD4:25 pmChicago O'Hare Intl
8h 35m
1 stop
OAK11:00 pmOakland
$280
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 September 15, 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

Thu 9/25

6:30 am-9:32 pm

1 stop13h 02m

Chicago O'Hare Intl

Sun 9/28

8:49 pm-11:32 pm

2 stops28h 43m

$255

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sat 10/18

3:25 pm-11:05 pm

1 stop5h 40m

Chicago O'Hare Intl

Tue 10/21

12:40 pm-7:45 pm

2 stops9h 05m

$256

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 11/13

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

$261

OaklandChicago

OAK - ORD

OAKORD

Oakland

Fri 11/14

7:12 pm-5:01 am

1 stop7h 49m

Chicago O'Hare Intl

Mon 11/17

2:05 pm-11:59 pm

2 stops11h 54m

$262

OaklandChicago

OAK - ORD

OAKORD

Oakland

Fri 9/26

6:30 am-4:59 pm

1 stop8h 29m

Chicago O'Hare Intl

Mon 9/29

6:05 pm-11:32 pm

1 stop7h 27m

$266

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sat 9/27

6:30 am-9:32 pm

1 stop13h 02m

Chicago O'Hare Intl

Mon 9/29

6:05 pm-11:32 pm

1 stop7h 27m

$267

OaklandChicago

OAK - ORD

OAKORD

Oakland

Fri 10/31

8:03 pm-6:22 am

1 stop8h 19m

Chicago O'Hare Intl

Tue 11/4

3:25 pm-11:59 pm

1 stop10h 34m

$276

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sat 11/15

5:45 am-4:28 pm

2 stops8h 43m

Chicago O'Hare Intl

Mon 11/17

7:40 pm-12:03 am

1 stop6h 23m

$282

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sun 11/9

5:45 am-6:26 pm

2 stops10h 41m

Chicago O'Hare Intl

Sat 11/15

2:30 pm-9:39 pm

2 stops9h 09m

$287

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sat 10/4

8:05 pm-6:24 am

1 stop8h 19m

Chicago O'Hare Intl

Sat 10/11

5:59 pm-12:03 am

1 stop8h 04m

$316

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 $399. 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 $513.

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 $413 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $465. 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 16% 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 September 2025, prices for Oakland, California to Chicago O'Hare Intl Airport flights are approximately 59% 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 5h 40m 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
8,015 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $163Free CancellationRating
7.4
8,929 reviews
Search United Airlines flights
SouthwestPriceFrom $242Free CancellationRating
8.0
4,242 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
Rockford
Schaumburg
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Racine
Hammond
Orland Park
Tinley Park
Elgin
Aurora
Janesville
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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