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Cheap flights from Oakland, California to Chicago from $111

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 4/11. 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.
Southwest Logo
3:00 pm - 11:55 pm
OAK
-
ORD
6h 55m
1 stop
Southwest Logo
3:05 pm - 9:45 pm
ORD
-
OAK
8h 40m
1 stop
$243Southwest
Tue, Apr 21 - Sat, Apr 25
Southwest Logo
6:10 am - 6:50 pm
OAK
-
ORD
10h 40m
2 stops
Southwest Logo
4:15 pm - 9:00 pm
ORD
-
OAK
6h 45m
1 stop
$248Southwest
Tue, Apr 21 - Sat, Apr 25
Southwest Logo
12:25 pm - 11:55 pm
OAK
-
ORD
9h 30m
2 stops
Southwest Logo
7:00 am - 4:55 pm
ORD
-
OAK
11h 55m
2 stops
$253Southwest
Tue, Apr 21 - Sat, Apr 25
Alaska Airlines Logo
7:19 pm - 1:13 pm
OAK
-
ORD
15h 54m
1 stop
Alaska Airlines Logo
7:59 pm - 10:17 am
ORD
-
OAK
16h 18m
1 stop
$257Alaska Airlines
Tue, Apr 28 - Mon, May 4
Southwest Logo
3:00 pm - 11:55 pm
OAK
-
ORD
6h 55m
1 stop
Southwest Logo
4:15 pm - 9:00 pm
ORD
-
OAK
6h 45m
1 stop
$265Southwest
Tue, Apr 21 - Sat, Apr 25
Alaska Airlines Logo
7:19 pm - 11:43 pm
OAK
-
ORD
26h 24m
1 stop
Alaska Airlines Logo
7:59 pm - 6:15 pm
ORD
-
OAK
24h 16m
1 stop
$269Alaska Airlines
Wed, Apr 22 - Thu, Apr 30
Southwest Logo
12:25 pm - 11:55 pm
OAK
-
ORD
9h 30m
2 stops
Southwest Logo
4:15 pm - 9:00 pm
ORD
-
OAK
6h 45m
1 stop
$270Southwest
Tue, Apr 21 - Sat, Apr 25
Alaska Airlines Logo
10:57 am - 11:59 pm
OAK
-
ORD
11h 02m
2 stops
Alaska Airlines Logo
7:59 pm - 10:17 am
ORD
-
OAK
16h 18m
1 stop
$271Alaska Airlines
Wed, Apr 29 - Fri, May 1
Alaska Airlines Logo
7:19 pm - 1:13 pm
OAK
-
ORD
15h 54m
1 stop
Alaska Airlines Logo
6:00 am - 10:32 pm
ORD
-
OAK
18h 32m
1 stop
$274Alaska Airlines
Wed, Apr 22 - Thu, Apr 30
Southwest Logo
11:10 am - 10:55 pm
OAK
-
ORD
9h 45m
2 stops
Southwest Logo
7:00 am - 4:55 pm
ORD
-
OAK
11h 55m
2 stops
$275Southwest
Tue, Apr 21 - Sat, Apr 25

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
Apr 28
OAK7:19 pmOakland
15h 54m
1 stop
ORD1:13 pmChicago O'Hare Intl
May 4
ORD7:59 pmChicago O'Hare Intl
16h 18m
1 stop
OAK10:17 amOakland
$257
Alaska Airlines
Apr 22
OAK7:19 pmOakland
26h 24m
1 stop
ORD11:43 pmChicago O'Hare Intl
Apr 30
ORD7:59 pmChicago O'Hare Intl
24h 16m
1 stop
OAK6:15 pmOakland
$269
Alaska Airlines
Apr 29
OAK10:57 amOakland
11h 02m
2 stops
ORD11:59 pmChicago O'Hare Intl
May 1
ORD7:59 pmChicago O'Hare Intl
16h 18m
1 stop
OAK10:17 amOakland
$271

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
Apr 21
OAK3:00 pmOakland
6h 55m
1 stop
ORD11:55 pmChicago O'Hare Intl
Apr 25
ORD3:05 pmChicago O'Hare Intl
8h 40m
1 stop
OAK9:45 pmOakland
$243
Southwest
Apr 21
OAK6:10 amOakland
10h 40m
2 stops
ORD6:50 pmChicago O'Hare Intl
Apr 25
ORD4:15 pmChicago O'Hare Intl
6h 45m
1 stop
OAK9:00 pmOakland
$248
Southwest
Apr 21
OAK12:25 pmOakland
9h 30m
2 stops
ORD11:55 pmChicago O'Hare Intl
Apr 25
ORD7:00 amChicago O'Hare Intl
11h 55m
2 stops
OAK4:55 pmOakland
$253

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 March 8, 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 4/21

3:00 pm-11:55 pm

1 stop6h 55m

Chicago O'Hare Intl

Sat 4/25

3:05 pm-9:45 pm

1 stop8h 40m

$243

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 4/21

6:10 am-6:50 pm

2 stops10h 40m

Chicago O'Hare Intl

Sat 4/25

4:15 pm-9:00 pm

1 stop6h 45m

$248

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 4/21

12:25 pm-11:55 pm

2 stops9h 30m

Chicago O'Hare Intl

Sat 4/25

7:00 am-4:55 pm

2 stops11h 55m

$253

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 4/28

7:19 pm-1:13 pm

1 stop15h 54m

Chicago O'Hare Intl

Mon 5/4

7:59 pm-10:17 am

1 stop16h 18m

$257
Quickest round-trip

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 4/21

3:00 pm-11:55 pm

1 stop6h 55m

Chicago O'Hare Intl

Sat 4/25

4:15 pm-9:00 pm

1 stop6h 45m

$265

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 4/22

7:19 pm-11:43 pm

1 stop26h 24m

Chicago O'Hare Intl

Thu 4/30

7:59 pm-6:15 pm

1 stop24h 16m

$269

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 4/21

12:25 pm-11:55 pm

2 stops9h 30m

Chicago O'Hare Intl

Sat 4/25

4:15 pm-9:00 pm

1 stop6h 45m

$270

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 4/29

10:57 am-11:59 pm

2 stops11h 02m

Chicago O'Hare Intl

Fri 5/1

7:59 pm-10:17 am

1 stop16h 18m

$271

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 4/22

7:19 pm-1:13 pm

1 stop15h 54m

Chicago O'Hare Intl

Thu 4/30

6:00 am-10:32 pm

1 stop18h 32m

$274

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 4/21

11:10 am-10:55 pm

2 stops9h 45m

Chicago O'Hare Intl

Sat 4/25

7:00 am-4:55 pm

2 stops11h 55m

$275

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 August is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Oakland, California averaging around $336.

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 $494.

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 $450. 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 10% 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 30m

Direct flights

None
The fastest flight from Oakland, California to Chicago O'Hare Intl Airport takes 6h 30m
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 30m 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
8,504 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $153Free CancellationRating
7.4
9,408 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $237Free CancellationRating
8.0
12,001 reviews
Search Alaska Airlines flights
SouthwestPriceFrom $246Free CancellationRating
8.0
4,313 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 1 time per week, with 4,313 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 $371 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
Schaumburg
South Haven
Rockford
Merrillville
Gurnee
Naperville
Rosemont
New Buffalo
Orland Park
Kenosha
Oak Brook
Joliet
Racine
Janesville
Hammond
Aurora
Tinley Park
Elgin
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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