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Cheap flights from Oakland, California to Chicago from $77

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 1/20. 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
11:08 am - 11:50 pm
OAK
-
ORD
10h 42m1 stop
Alaska Airlines Logo
6:06 pm - 4:23 pm
ORD
-
OAK
24h 17m1 stop
$154Alaska Airlines
Wed, Jan 14 - Tue, Jan 20
Southwest Logo
5:25 am - 1:30 pm
OAK
-
ORD
6h 05m1 stop
Southwest Logo
1:00 pm - 7:45 pm
ORD
-
OAK
8h 45m1 stop
$159Southwest
Wed, Jan 7 - Wed, Jan 14
Southwest Logo
5:25 am - 1:30 pm
OAK
-
ORD
6h 05m1 stop
Southwest Logo
2:15 pm - 9:25 pm
ORD
-
OAK
9h 10m2 stops
$164Southwest
Wed, Jan 7 - Wed, Jan 14
Alaska Airlines Logo
5:17 pm - 11:50 pm
OAK
-
ORD
28h 33m1 stop
Alaska Airlines Logo
8:00 am - 4:28 pm
ORD
-
OAK
10h 28m1 stop
$169Alaska Airlines
Mon, Jan 12 - Sat, Jan 17
Alaska Airlines Logo
8:03 pm - 1:10 pm
OAK
-
ORD
15h 07m1 stop
Alaska Airlines Logo
8:00 am - 4:23 pm
ORD
-
OAK
10h 23m1 stop
$176Alaska Airlines
Mon, Feb 9 - Wed, Feb 11
Alaska Airlines Logo
11:43 am - 5:10 pm
OAK
-
ORD
27h 27m1 stop
Alaska Airlines Logo
6:06 pm - 4:28 pm
ORD
-
OAK
24h 22m1 stop
$181Alaska Airlines
Tue, Jan 20 - Fri, Jan 23
Alaska Airlines Logo
8:10 am - 11:50 pm
OAK
-
ORD
13h 40m1 stop
Alaska Airlines Logo
8:00 am - 4:28 pm
ORD
-
OAK
10h 28m1 stop
$184Alaska Airlines
Sat, Jan 17 - Sat, Jan 24
Southwest Logo
10:20 am - 10:35 pm
OAK
-
ORD
10h 15m2 stops
Southwest Logo
2:15 pm - 9:25 pm
ORD
-
OAK
9h 10m2 stops
$185Southwest
Wed, Jan 7 - Wed, Jan 14
Alaska Airlines Logo
11:08 am - 11:50 pm
OAK
-
ORD
10h 42m1 stop
Alaska Airlines Logo
8:00 am - 9:46 am
ORD
-
OAK
27h 46m2 stops
$187Alaska Airlines
Wed, Jan 14 - Tue, Jan 20
Alaska Airlines Logo
6:15 am - 11:56 pm
OAK
-
ORD
15h 41m1 stop
Alaska Airlines Logo
7:00 am - 4:37 pm
ORD
-
OAK
11h 37m1 stop
$190Alaska Airlines
Tue, Mar 3 - Wed, Mar 4

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
Jan 7
OAK5:25 amOakland
6h 05m
1 stop
ORD1:30 pmChicago O'Hare Intl
Jan 14
ORD1:00 pmChicago O'Hare Intl
8h 45m
1 stop
OAK7:45 pmOakland
$159
Find similar
Southwest
Jan 12
OAK5:25 amOakland
6h 05m
1 stop
ORD1:30 pmChicago O'Hare Intl
Jan 21
ORD7:15 amChicago O'Hare Intl
7h 40m
1 stop
OAK12:55 pmOakland
$162
Find similar
Southwest
Jan 7
OAK5:25 amOakland
6h 05m
1 stop
ORD1:30 pmChicago O'Hare Intl
Jan 14
ORD2:15 pmChicago O'Hare Intl
9h 10m
2 stops
OAK9:25 pmOakland
$164
Find similar

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 14
OAK11:08 amOakland
10h 42m
1 stop
ORD11:50 pmChicago O'Hare Intl
Jan 20
ORD6:06 pmChicago O'Hare Intl
24h 17m
1 stop
OAK4:23 pmOakland
$154
Find similar
Alaska Airlines
Jan 12
OAK5:17 pmOakland
28h 33m
1 stop
ORD11:50 pmChicago O'Hare Intl
Jan 17
ORD8:00 amChicago O'Hare Intl
10h 28m
1 stop
OAK4:28 pmOakland
$169
Find similar
Alaska Airlines
Feb 9
OAK8:03 pmOakland
15h 07m
1 stop
ORD1:10 pmChicago O'Hare Intl
Feb 11
ORD8:00 amChicago O'Hare Intl
10h 23m
1 stop
OAK4:23 pmOakland
$176
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 December 4, 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

Wed 1/14

11:08 am-11:50 pm

1 stop10h 42m

Chicago O'Hare Intl

Tue 1/20

6:06 pm-4:23 pm

1 stop24h 17m

$154

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 1/7

5:25 am-1:30 pm

1 stop6h 05m

Chicago O'Hare Intl

Wed 1/14

1:00 pm-7:45 pm

1 stop8h 45m

$159

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 1/7

5:25 am-1:30 pm

1 stop6h 05m

Chicago O'Hare Intl

Wed 1/14

2:15 pm-9:25 pm

2 stops9h 10m

$164

OaklandChicago

OAK - ORD

OAKORD

Oakland

Mon 1/12

5:17 pm-11:50 pm

1 stop28h 33m

Chicago O'Hare Intl

Sat 1/17

8:00 am-4:28 pm

1 stop10h 28m

$169

OaklandChicago

OAK - ORD

OAKORD

Oakland

Mon 2/9

8:03 pm-1:10 pm

1 stop15h 07m

Chicago O'Hare Intl

Wed 2/11

8:00 am-4:23 pm

1 stop10h 23m

$176

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 1/20

11:43 am-5:10 pm

1 stop27h 27m

Chicago O'Hare Intl

Fri 1/23

6:06 pm-4:28 pm

1 stop24h 22m

$181

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sat 1/17

8:10 am-11:50 pm

1 stop13h 40m

Chicago O'Hare Intl

Sat 1/24

8:00 am-4:28 pm

1 stop10h 28m

$184

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 1/7

10:20 am-10:35 pm

2 stops10h 15m

Chicago O'Hare Intl

Wed 1/14

2:15 pm-9:25 pm

2 stops9h 10m

$185

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 1/14

11:08 am-11:50 pm

1 stop10h 42m

Chicago O'Hare Intl

Tue 1/20

8:00 am-9:46 am

2 stops27h 46m

$187

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 3/3

6:15 am-11:56 pm

1 stop15h 41m

Chicago O'Hare Intl

Wed 3/4

7:00 am-4:37 pm

1 stop11h 37m

$190

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 February is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Oakland, California averaging around $273.

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 $500.

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 $410 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $462. 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 9% 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 December 2025, prices for Oakland, California to Chicago O'Hare Intl Airport flights are approximately 134% 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 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
8,161 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $163Free CancellationRating
7.4
9,063 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $189Free CancellationRating
8.0
11,396 reviews
Search Alaska Airlines flights
SouthwestPriceFrom $246Free CancellationRating
8.0
4,253 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
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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