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$129+ 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 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — OAK
May 19 — May 261
Tue 5/19
Tue 5/26
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 April 19, 2026.

This Alaska Airlines deal was found by Cheapflights users on 4/17. 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.
Wed 5/202:10 pm
ORD
-
OAK
1 stop11h 40m
Alaska Airlines
Tue 5/262:58 pm
OAK
-
ORD
1 stop20h 16m
Alaska Airlines
Deal found 4/17$257
This Alaska Airlines deal was found by Cheapflights users on 4/16. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/279:00 am
ORD
-
OAK
1 stop7h 14m
Alaska Airlines
Mon 6/12:58 pm
OAK
-
ORD
1 stop6h 57m
Alaska Airlines
Deal found 4/16$271
This CheapOair deal was found by Cheapflights users on 4/14. 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.
Wed 7/17:59 pm
ORD
-
OAK
1 stop15h 58m
Alaska Airlines
Tue 7/78:15 pm
OAK
-
ORD
1 stop15h 06m
Alaska Airlines
Deal found 4/14$274
This Alaska Airlines deal was found by Cheapflights users on 4/16. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/279:00 am
ORD
-
OAK
1 stop7h 14m
Alaska Airlines
Wed 6/310:29 am
OAK
-
ORD
1 stop6h 21m
Alaska Airlines
Deal found 4/16$280
This CheapOair deal was found by Cheapflights users on 4/14. 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 5/77:59 pm
ORD
-
OAK
1 stop16h 18m
Alaska Airlines
Sat 5/168:15 pm
OAK
-
ORD
1 stop14h 59m
Alaska Airlines
Deal found 4/14$285
This CheapOair deal was found by Cheapflights users on 4/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/17:59 pm
ORD
-
OAK
1 stop16h 18m
Alaska Airlines
Sat 5/93:18 pm
OAK
-
ORD
1 stop19h 55m
Alaska Airlines
Deal found 4/16$288
This CheapOair deal was found by Cheapflights users on 4/15. 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.
Tue 6/99:00 am
ORD
-
OAK
1 stop16h 50m
Alaska Airlines
Tue 6/238:15 pm
OAK
-
ORD
1 stop15h 06m
Alaska Airlines
Deal found 4/15$290
This Delta deal was found by Cheapflights users on 4/16. 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.
Fri 5/297:45 pm
ORD
-
OAK
1 stop6h 12m
Delta
Tue 6/212:28 pm
OAK
-
ORD
1 stop7h 22m
Delta
Deal found 4/16$291
This Alaska Airlines deal was found by Cheapflights users on 4/16. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/239:00 am
ORD
-
OAK
1 stop7h 14m
Alaska Airlines
Thu 5/282:58 pm
OAK
-
ORD
1 stop6h 57m
Alaska Airlines
Deal found 4/16$294
This Delta deal was found by Cheapflights users on 4/16. 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.
Thu 5/283:47 pm
ORD
-
OAK
2 stops10h 10m
Delta
Mon 6/112:28 pm
OAK
-
ORD
1 stop7h 22m
Delta
Deal found 4/16$296
This Alaska Airlines deal was found by Cheapflights users on 4/16. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/239:00 am
ORD
-
OAK
1 stop7h 14m
Alaska Airlines
Sun 5/247:00 am
OAK
-
ORD
1 stop7h 48m
Alaska Airlines
Deal found 4/16$297
This CheapOair deal was found by Cheapflights users on 4/15. 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.
Wed 5/68:50 am
ORD
-
OAK
1 stop7h 48m
Alaska Airlines
Sun 5/106:20 am
OAK
-
ORD
1 stop8h 36m
Alaska Airlines
Deal found 4/15$298

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 April 19, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$257
(CheapOair)

One-way from

$129
(CheapOair)

Popular in

February

Cheapest in

September

Average price

$264
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. 12% potential increase in price ($51 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 April 19, 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

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Fri 5/29

7:45 pm-11:57 pm

1 stop6h 12m

Oakland

Mon 6/1

12:28 pm-9:50 pm

1 stop7h 22m

$291

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Fri 5/1

7:59 pm-10:17 am

1 stop16h 18m

Oakland

Mon 5/4

3:18 pm-11:43 pm

1 stop6h 25m

$291

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Tue 5/5

6:00 am-1:15 pm

1 stop9h 15m

Oakland

Wed 5/6

2:09 pm-11:59 pm

1 stop7h 50m

$291

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Sat 5/2

2:09 pm-9:41 pm

1 stop9h 32m

Oakland

Wed 5/6

12:34 pm-9:45 pm

1 stop7h 11m

$291

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Tue 5/5

6:25 am-4:24 pm

2 stops11h 59m

Oakland

Wed 5/6

12:34 pm-9:45 pm

1 stop7h 11m

$296

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Thu 6/11

7:37 pm-11:54 pm

1 stop6h 17m

Oakland

Sat 6/13

6:00 am-4:30 pm

2 stops8h 30m

$364

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Fri 5/15

6:15 am-10:35 am

1 stop6h 20m

Oakland

Mon 5/18

9:20 am-6:35 pm

1 stop7h 15m

$372

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Wed 5/20

10:30 am-5:05 pm

2 stops8h 35m

Oakland

Tue 5/26

3:00 pm-11:55 pm

1 stop6h 55m

$377

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Wed 6/24

6:20 am-2:10 pm

1 stop9h 50m

Oakland

Wed 7/1

8:15 pm-11:36 pm

1 stop25h 21m

$387

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Wed 4/29

6:00 am-1:15 pm

1 stop9h 15m

Oakland

Tue 5/12

9:33 am-11:59 pm

2 stops12h 26m

$393

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/16

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

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 April.
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, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Oakland, California (average of $251). Flying from Chicago O'Hare Intl Airport to Oakland, California in February is currently the most expensive (average of $548). 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 April 19, 2026.
Read through reviews of airlines operating flights from Chicago O'Hare Intl Airport to Oakland, such as Southwest and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,329 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,329 reviews
Southwest
8.0
Very good
4,329 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,426 reviews
Southwest
8.0
Very good
4,329 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 12m. Your travel time can differ by up to 10h 06m. 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 $245, Southwest will fly you from Chicago O'Hare Intl Airport to Oakland, California and back. In addition to Southwest, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on Delta for as low as $264. Southwest is 34% 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 $118 on Southwest. Other airlines that offer cheap prices include Delta from $118 and Alaska Airlines from $158 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, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Oakland, California (average of $251). Flying from Chicago O'Hare Intl Airport to Oakland, California in February is currently the most expensive (average of $548). 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

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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 April 19, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$245Average$417FlexibilityNo cancel feeOn-time63%
DeltaCheapest$264Average$355FlexibilityNo cancel feeOn-timeN/A

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