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Cheap flights from Oakland, California to Chicago from $114

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.
Delta Logo
12:34 pm - 9:18 pm
OAK
-
ORD
6h 44m
1 stop
Delta Logo
7:35 am - 11:53 am
ORD
-
OAK
6h 18m
1 stop
$227Delta
Tue, Apr 14 - Wed, Apr 22
Delta Logo
12:34 pm - 9:18 pm
OAK
-
ORD
6h 44m
1 stop
Delta Logo
1:29 pm - 9:41 pm
ORD
-
OAK
10h 12m
2 stops
$232Delta
Tue, Apr 14 - Sat, Apr 18
Delta Logo
5:55 am - 3:18 pm
OAK
-
ORD
7h 23m
1 stop
Delta Logo
7:10 pm - 11:54 pm
ORD
-
OAK
6h 44m
1 stop
$237Delta
Sat, Apr 11 - Tue, Apr 14
Alaska Airlines Logo
2:09 pm - 11:59 pm
OAK
-
ORD
7h 50m
1 stop
Alaska Airlines Logo
6:00 am - 1:15 pm
ORD
-
OAK
9h 15m
1 stop
$242Alaska Airlines
Wed, Apr 22 - Wed, Apr 29
Delta Logo
6:00 am - 6:05 pm
OAK
-
ORD
10h 05m
2 stops
Delta Logo
2:00 pm - 11:57 pm
ORD
-
OAK
11h 57m
2 stops
$247Delta
Fri, May 29 - Tue, Jun 2
Alaska Airlines Logo
2:09 pm - 11:59 pm
OAK
-
ORD
7h 50m
1 stop
Alaska Airlines Logo
6:00 am - 1:15 pm
ORD
-
OAK
9h 15m
1 stop
$256Alaska Airlines
Wed, Apr 22 - Sat, Apr 25
Alaska Airlines Logo
2:09 pm - 11:59 pm
OAK
-
ORD
7h 50m
1 stop
Alaska Airlines Logo
6:00 am - 1:15 pm
ORD
-
OAK
9h 15m
1 stop
$257Alaska Airlines
Tue, Apr 28 - Wed, Apr 29
Alaska Airlines Logo
2:09 pm - 11:59 pm
OAK
-
ORD
7h 50m
1 stop
Alaska Airlines Logo
6:00 am - 1:15 pm
ORD
-
OAK
9h 15m
1 stop
$261Alaska Airlines
Wed, Apr 22 - Sat, Apr 25
Alaska Airlines Logo
2:09 pm - 11:59 pm
OAK
-
ORD
7h 50m
1 stop
Alaska Airlines Logo
8:50 am - 2:38 pm
ORD
-
OAK
7h 48m
1 stop
$262Alaska Airlines
Wed, Apr 22 - Tue, Apr 28
Alaska Airlines Logo
3:18 pm - 11:43 pm
OAK
-
ORD
6h 25m
1 stop
Alaska Airlines Logo
3:52 pm - 10:23 pm
ORD
-
OAK
8h 31m
1 stop
$264Alaska Airlines
Mon, May 4 - Mon, May 11

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 22
OAK2:09 pmOakland
7h 50m
1 stop
ORD11:59 pmChicago O'Hare Intl
Apr 29
ORD6:00 amChicago O'Hare Intl
9h 15m
1 stop
OAK1:15 pmOakland
$242
Alaska Airlines
Apr 22
OAK2:09 pmOakland
7h 50m
1 stop
ORD11:59 pmChicago O'Hare Intl
Apr 25
ORD6:00 amChicago O'Hare Intl
9h 15m
1 stop
OAK1:15 pmOakland
$256
Alaska Airlines
Apr 28
OAK2:09 pmOakland
7h 50m
1 stop
ORD11:59 pmChicago O'Hare Intl
Apr 29
ORD6:00 amChicago O'Hare Intl
9h 15m
1 stop
OAK1:15 pmOakland
$257

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 14
OAK11:10 amOakland
9h 45m
2 stops
ORD10:55 pmChicago O'Hare Intl
Apr 21
ORD7:45 amChicago O'Hare Intl
9h 45m
2 stops
OAK3:30 pmOakland
$267
Southwest
May 6
OAK3:00 pmOakland
6h 55m
1 stop
ORD11:55 pmChicago O'Hare Intl
May 9
ORD7:00 amChicago O'Hare Intl
7h 25m
1 stop
OAK12:25 pmOakland
$271
Southwest
May 6
OAK11:10 amOakland
9h 45m
2 stops
ORD10:55 pmChicago O'Hare Intl
May 9
ORD4:15 pmChicago O'Hare Intl
6h 45m
1 stop
OAK9:00 pmOakland
$276

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 23, 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
Quickest round-trip

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 4/14

12:34 pm-9:18 pm

1 stop6h 44m

Chicago O'Hare Intl

Wed 4/22

7:35 am-11:53 am

1 stop6h 18m

$227

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 4/14

12:34 pm-9:18 pm

1 stop6h 44m

Chicago O'Hare Intl

Sat 4/18

1:29 pm-9:41 pm

2 stops10h 12m

$232

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sat 4/11

5:55 am-3:18 pm

1 stop7h 23m

Chicago O'Hare Intl

Tue 4/14

7:10 pm-11:54 pm

1 stop6h 44m

$237

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 4/22

2:09 pm-11:59 pm

1 stop7h 50m

Chicago O'Hare Intl

Wed 4/29

6:00 am-1:15 pm

1 stop9h 15m

$242

OaklandChicago

OAK - ORD

OAKORD

Oakland

Fri 5/29

6:00 am-6:05 pm

2 stops10h 05m

Chicago O'Hare Intl

Tue 6/2

2:00 pm-11:57 pm

2 stops11h 57m

$247

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 4/22

2:09 pm-11:59 pm

1 stop7h 50m

Chicago O'Hare Intl

Sat 4/25

6:00 am-1:15 pm

1 stop9h 15m

$256

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 4/28

2:09 pm-11:59 pm

1 stop7h 50m

Chicago O'Hare Intl

Wed 4/29

6:00 am-1:15 pm

1 stop9h 15m

$257

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 4/22

2:09 pm-11:59 pm

1 stop7h 50m

Chicago O'Hare Intl

Sat 4/25

6:00 am-1:15 pm

1 stop9h 15m

$261

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 4/22

2:09 pm-11:59 pm

1 stop7h 50m

Chicago O'Hare Intl

Tue 4/28

8:50 am-2:38 pm

1 stop7h 48m

$262

OaklandChicago

OAK - ORD

OAKORD

Oakland

Mon 5/4

3:18 pm-11:43 pm

1 stop6h 25m

Chicago O'Hare Intl

Mon 5/11

3:52 pm-10:23 pm

1 stop8h 31m

$264

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 $402. 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 $499.

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 $451. 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 7% 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 25m

Direct flights

None
The fastest flight from Oakland, California to Chicago O'Hare Intl Airport takes 6h 25m
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 25m 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
8,533 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $163Free CancellationRating
7.4
9,459 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $237Free CancellationRating
7.9
12,094 reviews
Search Alaska Airlines flights
SouthwestPriceFrom $246Free CancellationRating
8.0
4,325 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 4,325 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
Rosemont
Naperville
New Buffalo
Orland Park
Kenosha
Oak Brook
Joliet
Janesville
Racine
Hammond
Aurora
Elgin
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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