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$73+ 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 4/25. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — OAK
Mar 20 — Mar 271
Fri 3/20
Fri 3/27
1 adult, Economy
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Cheap 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 February 18, 2026.

This Alaska Airlines deal was found by Cheapflights users on 2/17. 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.
Fri 5/13:52 pm
ORD
-
OAK
1 stop8h 31m
Alaska Airlines
Sun 5/36:55 pm
OAK
-
ORD
1 stop16h 18m
Alaska Airlines
Deal found 2/17$223
This Delta deal was found by Cheapflights users on 2/16. 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 4/147:10 pm
ORD
-
OAK
1 stop6h 44m
Delta
Fri 4/1712:34 pm
OAK
-
ORD
1 stop6h 44m
Delta
Deal found 2/16$237
This Alaska Airlines deal was found by Cheapflights users on 2/17. 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.
Fri 5/13:52 pm
ORD
-
OAK
1 stop8h 31m
Alaska Airlines
Mon 5/43:18 pm
OAK
-
ORD
1 stop19h 55m
Alaska Airlines
Deal found 2/17$253
This Alaska Airlines deal was found by Cheapflights users on 2/15. 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 4/73:22 pm
ORD
-
OAK
1 stop10h 21m
Alaska Airlines
Wed 4/222:09 pm
OAK
-
ORD
1 stop7h 50m
Alaska Airlines
Deal found 2/15$255
This CheapOair deal was found by Cheapflights users on 2/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/287:59 pm
ORD
-
OAK
1 stop20h 15m
Alaska Airlines
Thu 6/46:02 am
OAK
-
ORD
1 stop15h 53m
Alaska Airlines
Deal found 2/15$257
This CheapOair deal was found by Cheapflights users on 2/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/243:52 pm
ORD
-
OAK
1 stop8h 31m
Alaska Airlines
Sat 5/26:46 am
OAK
-
ORD
2 stops15h 13m
Alaska Airlines
Deal found 2/14$258
This Alaska Airlines deal was found by Cheapflights users on 2/14. 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 5/133:43 pm
ORD
-
OAK
1 stop9h 54m
Alaska Airlines
Mon 5/183:12 pm
OAK
-
ORD
1 stop25h 34m
Alaska Airlines
Deal found 2/14$263
This CheapOair deal was found by Cheapflights users on 2/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/243:52 pm
ORD
-
OAK
1 stop8h 31m
Alaska Airlines
Thu 4/302:09 pm
OAK
-
ORD
1 stop7h 50m
Alaska Airlines
Deal found 2/17$265
This Southwest deal was found by Cheapflights users on 2/15. 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 4/16:15 am
ORD
-
OAK
1 stop8h 15m
Southwest
Tue 4/76:35 am
OAK
-
ORD
1 stop6h 25m
Southwest
Deal found 2/15$267
This CheapOair deal was found by Cheapflights users on 2/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/238:50 am
ORD
-
OAK
1 stop7h 48m
Alaska Airlines
Mon 4/273:18 pm
OAK
-
ORD
2 stops13h 22m
Alaska Airlines
Deal found 2/14$272
This CheapOair deal was found by Cheapflights users on 2/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/157:59 pm
ORD
-
OAK
1 stop15h 46m
Alaska Airlines
Wed 5/2010:29 am
OAK
-
ORD
1 stop6h 21m
Alaska Airlines
Deal found 2/17$273

Find 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 February 18, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$223
(CheapOair)

One-way from

$73
(Southwest)

Popular in

April

Cheapest in

September

Average price

$548
Provider with most accurate pricing for Chicago O'Hare Intl-Oakland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago O'Hare Intl-Oakland flights.
Search Deals
From Chicago O'Hare Intl to Oakland
Search Deals
One-way flight from Chicago O'Hare Intl to Oakland
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($59 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

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 February 18, 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

Fri 5/1

3:52 pm-10:23 pm

1 stop8h 31m

Oakland

Sun 5/3

6:55 pm-1:13 pm

1 stop16h 18m

$223

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Mon 4/6

7:10 pm-11:46 pm

1 stop6h 36m

Oakland

Tue 4/21

12:34 pm-9:18 pm

1 stop6h 44m

$237

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Tue 4/7

3:22 pm-11:43 pm

1 stop10h 21m

Oakland

Wed 4/22

2:09 pm-11:59 pm

1 stop7h 50m

$255

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Tue 5/12

4:50 pm-10:35 pm

1 stop7h 45m

Oakland

Tue 5/19

12:25 pm-11:55 pm

2 stops9h 30m

$283

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Wed 4/8

3:22 pm-11:43 pm

1 stop10h 21m

Oakland

Wed 4/22

2:09 pm-11:59 pm

1 stop7h 50m

$295

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Mon 4/6

7:10 pm-11:46 pm

1 stop6h 36m

Oakland

Mon 4/20

5:04 pm-8:38 am

2 stops13h 34m

$301

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Tue 4/14

8:32 pm-11:54 pm

2 stops29h 22m

Oakland

Sat 4/18

12:34 pm-9:18 pm

1 stop6h 44m

$301

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Sun 3/8

7:10 pm-11:46 pm

1 stop6h 36m

Oakland

Tue 3/10

12:35 pm-9:34 pm

1 stop6h 59m

$308

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Mon 3/9

7:20 am-11:51 am

1 stop6h 31m

Oakland

Wed 3/11

5:55 am-4:43 pm

2 stops8h 48m

$313

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Tue 3/10

7:20 am-11:51 am

1 stop6h 31m

Oakland

Tue 3/17

12:35 pm-9:34 pm

1 stop6h 59m

$319

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/15

Showing 1-10 of 18 results
1
2

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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago O'Hare Intl Airport-Oakland, California flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 February is currently the most expensive (average of $211). 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.

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 February 18, 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
4,290 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Comfort

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
4,290 reviews
Southwest
8.0
Very good
4,290 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Comfort

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
8,465 reviews
Southwest
8.0
Very good
4,290 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Comfort

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, Delta, and Southwest can get you from Chicago O'Hare Intl Airport to Oakland, California in just under 6h 18m. Your travel time can differ by up to 2h 13m. 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 $83, 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 79% 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 February is currently the most expensive (average of $211). 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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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 February 18, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$83Average$229FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$236Average$442FlexibilityNo cancel feeOn-time63%

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