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$132+ Cheap flights from O'Hare Intl (ORD) to Oakland, CA (OAK)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/29. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — OAK
Feb 11 — Feb 181
Wed 2/11
Wed 2/18
1 adult, Economy
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Cheap flight deals from O'Hare Intl to Oakland

Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) to Oakland (OAK). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 12, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$263
(Alaska Airlines)

One-way from

$132
(Alaska Airlines)

Popular in

April

Cheapest in

September

Average price

$416
Provider with most accurate pricing for Chicago O'Hare Intl-Oakland flight deals.
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Provider most trusted by Cheapflights users for Chicago O'Hare Intl-Oakland flights.
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From Chicago O'Hare Intl to Oakland
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One-way flight from Chicago O'Hare Intl to Oakland
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Highest demand for flights based on searches. 9% potential increase in price ($42 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Find flight deals from O'Hare Intl to Oakland

Cheapest flights from O'Hare Intl to Oakland
Explore the most affordable flight options available from O'Hare Intl to Oakland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 12, 2026.

This Alaska Airlines deal was found by Cheapflights users on 1/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/53:52 pm
ORD
-
OAK
1 stop24h 28m
Alaska Airlines
Fri 5/87:19 pm
OAK
-
ORD
1 stop21h 44m
Alaska Airlines
Deal found 1/9$263
This Kiwi.com deal was found by Cheapflights users on 1/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/263:54 pm
ORD
-
OAK
1 stop8h 55m
Hawaiian Airlines
Thu 3/56:15 am
OAK
-
ORD
1 stop8h 18m
Hawaiian Airlines
Deal found 1/12$264
This Orbitz deal was found by Cheapflights users on 1/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/102:06 pm
ORD
-
OAK
1 stop21h 40m
Alaska Airlines
Sun 2/226:15 am
OAK
-
ORD
1 stop15h 41m
Alaska Airlines
Deal found 1/12$270
This Alaska Airlines deal was found by Cheapflights users on 1/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/237:59 pm
ORD
-
OAK
1 stop24h 40m
Alaska Airlines
Wed 4/297:00 am
OAK
-
ORD
1 stop10h 03m
Alaska Airlines
Deal found 1/11$273
This Southwest deal was found by Cheapflights users on 1/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/114:25 pm
ORD
-
OAK
1 stop7h 20m
Southwest
Wed 2/187:20 am
OAK
-
ORD
1 stop6h 05m
Southwest
Deal found 1/12$275
This Delta deal was found by Cheapflights users on 1/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/247:15 am
ORD
-
OAK
1 stop6h 40m
Delta
Tue 3/1712:35 pm
OAK
-
ORD
1 stop6h 59m
Delta
Deal found 1/10$276
This Delta deal was found by Cheapflights users on 1/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/77:05 pm
ORD
-
OAK
1 stop6h 41m
Delta
Tue 4/1412:33 pm
OAK
-
ORD
1 stop7h 02m
Delta
Deal found 1/10$277
This Alaska Airlines deal was found by Cheapflights users on 1/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/118:00 am
ORD
-
OAK
1 stop10h 23m
Alaska Airlines
Wed 2/186:15 am
OAK
-
ORD
1 stop8h 18m
Alaska Airlines
Deal found 1/12$279
This Alaska Airlines deal was found by Cheapflights users on 1/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/263:54 pm
ORD
-
OAK
1 stop8h 55m
Alaska Airlines
Wed 3/186:40 pm
OAK
-
ORD
1 stop9h 59m
Alaska Airlines
Deal found 1/10$280
This Alaska Airlines deal was found by Cheapflights users on 1/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/263:54 pm
ORD
-
OAK
1 stop8h 55m
Alaska Airlines
Sun 3/16:15 am
OAK
-
ORD
1 stop27h 46m
Alaska Airlines
Deal found 1/12$283

Cheapflights Fare Finder

 
Customize your flight search to find flights from O'Hare Intl to Oakland 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, Cheapflights users made 2,558,603 searches. Data last updated January 12, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Oakland that are best for you.

Fly from

O'Hare Intl

Fly to

Oakland

Route

Depart

Return

Price

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Tue 5/5

3:52 pm-2:20 pm

1 stop24h 28m

Oakland

Fri 5/8

7:19 pm-7:03 pm

1 stop21h 44m

$263

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Thu 4/23

7:59 pm-9:53 am

1 stop15h 54m

Oakland

Mon 4/27

7:19 pm-2:41 pm

1 stop17h 22m

$273

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Tue 4/7

7:05 pm-11:46 pm

1 stop6h 41m

Oakland

Tue 4/14

12:33 pm-9:35 pm

1 stop7h 02m

$277

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Tue 3/17

3:54 pm-10:49 pm

1 stop8h 55m

Oakland

Wed 3/18

6:40 pm-6:39 am

1 stop9h 59m

$277

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Wed 2/11

8:00 am-4:23 pm

1 stop10h 23m

Oakland

Wed 2/18

6:15 am-4:33 pm

1 stop8h 18m

$279

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Wed 2/25

3:54 pm-10:49 pm

1 stop8h 55m

Oakland

Sat 2/28

6:15 am-11:56 pm

1 stop15h 41m

$279

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Tue 2/24

7:00 am-4:37 pm

1 stop11h 37m

Oakland

Sat 2/28

6:15 am-11:56 pm

1 stop15h 41m

$279

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Thu 4/23

7:59 pm-10:37 pm

1 stop28h 38m

Oakland

Sun 4/26

7:19 pm-11:43 pm

1 stop26h 24m

$283

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Thu 2/26

3:54 pm-10:49 pm

1 stop8h 55m

Oakland

Sun 3/1

6:15 am-12:01 pm

1 stop27h 46m

$283

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Wed 2/11

7:15 am-7:50 pm

2 stops14h 35m

Oakland

Wed 2/18

11:05 am-10:35 pm

2 stops9h 30m

$286

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/11

Showing 1-10 of 24 results
1
2
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Compare providers for flights from O'Hare Intl to Oakland

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from O'Hare Intl to Oakland in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago O'Hare Intl Airport-Oakland, California flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago O'Hare Intl Airport-Oakland, California flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago O'Hare Intl Airport-Oakland, California flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago O'Hare Intl Airport-Oakland, California flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago O'Hare Intl Airport-Oakland, California flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from O'Hare Intl to Oakland

Have a flexible travel schedule? Discover the best time to fly to Oakland from O'Hare Intl with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago O'Hare Intl Airport to Oakland

What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Oakland, California?

Currently, October is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Oakland, California (average of $80). Flying from Chicago O'Hare Intl Airport to Oakland, California in November is currently the most expensive (average of $207). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

How much does it cost to fly round-trip from Chicago O'Hare Intl Airport to Oakland, California?

Reviews of airlines servicing Oakland

Get insights into the airlines that provide service to Oakland. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Oakland. Reviews last updated January 12, 2026.
Read through reviews of airlines operating flights from Chicago O'Hare Intl Airport to Oakland, such as Southwest and Spirit Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,255 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,255 reviews
Southwest
8.0
Very good
4,255 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Spirit Airlines
6.3
Okay
8,297 reviews
Southwest
8.0
Very good
4,255 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Related info for your journey

Find useful and relevant information for your journey from O'Hare Intl to Oakland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Oakland from Chicago O'Hare Intl?

    Oakland (OAK), located 7.0 mi from the city center, is the airport you fly into when you book flights from Chicago O'Hare Intl to Oakland. 2 airlines have flights to Oakland from Chicago O'Hare Intl on a regular basis. Booking flights from Chicago O'Hare Intl to Oakland should not be difficult; the airport handles an average of 0 inbound flights from Chicago O'Hare Intl per day.

  • How long is the flight from Chicago O'Hare Intl Airport to Oakland, California?

    Alaska Airlines and Delta can get you from Chicago O'Hare Intl Airport to Oakland, California in just under 6h 41m. Your travel time can differ by up to 17h 47m. Airlines will cover a distance of 1830 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines flying from Chicago O'Hare Intl Airport to Oakland, California round-trip?

    Currently priced at $53, Spirit Airlines will fly you from Chicago O'Hare Intl Airport to Oakland, California and back. In addition to Spirit Airlines, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on Southwest for as low as $236. Spirit Airlines is 85% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Chicago O'Hare Intl Airport to Oakland, California one-way?

    One-way options have recently been found by users for as low as $98 on Alaska Airlines. Other airlines that offer cheap prices include Southwest from $108 and Delta from $137 one-way.

  • Can I find deals for flights from O'Hare Intl to Oakland that include hotel bookings?

    Yes. In addition to deals on O'Hare Intl to Oakland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from O'Hare Intl to Oakland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from O'Hare Intl to Oakland.

  • Can I find deals for business class flights from O'Hare Intl to Oakland?

    Yes. Cheapflights offers flight deals from O'Hare Intl to Oakland by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Oakland, California?

    Currently, October is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Oakland, California (average of $80). Flying from Chicago O'Hare Intl Airport to Oakland, California in November is currently the most expensive (average of $207). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Alternative routes for O'Hare Intl to Oakland

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from O'Hare Intl to Oakland

Discover the top 2 airlines that operate flights from O'Hare Intl to Oakland. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$83Average$223FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$236Average$419FlexibilityNo cancel feeOn-time63%

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