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O'Hare Intl

$119+ Cheap flights from Oakland, CA (OAK) to O'Hare Intl (ORD)

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 1/17. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — ORD
Jan 14 — Jan 211
Wed 1/14
Wed 1/21
1 adult, Economy
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Cheap flight deals from Oakland to O'Hare Intl

Cheapest flights from Oakland to O'Hare Intl
Explore the most affordable flight options available from Oakland to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 15, 2025.

This Delta deal was found by Cheapflights users on 12/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2512:34 pmOAK - ORD
1 stop7h 02mDelta
Mon 1/57:30 amORD - OAK
2 stops17h 23mDelta
Deal found 12/14$400
This Southwest deal was found by Cheapflights users on 12/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/245:25 amOAK - ORD
1 stop6h 05mSouthwest
Thu 12/252:15 pmORD - OAK
1 stop8h 20mSouthwest
Deal found 12/14$469
This Alaska Airlines deal was found by Cheapflights users on 12/15. 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 12/162:31 pmOAK - ORD
1 stop7h 28mAlaska Airlines
Wed 1/78:00 amORD - OAK
1 stop10h 23mAlaska Airlines
Deal found 12/15$481
This Alaska Airlines deal was found by Cheapflights users on 12/13. 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 12/189:35 amOAK - ORD
1 stop17h 27mAlaska Airlines
Sat 1/173:35 pmORD - OAK
1 stop20h 53mAlaska Airlines
Deal found 12/13$483
This Delta deal was found by Cheapflights users on 12/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/165:55 amOAK - ORD
2 stops9h 02mDelta
Wed 1/77:20 amORD - OAK
1 stop6h 37mDelta
Deal found 12/15$487
This Alaska Airlines deal was found by Cheapflights users on 12/14. 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.
Mon 12/156:40 amOAK - ORD
1 stop8h 15mAlaska Airlines
Mon 1/56:00 amORD - OAK
1 stop29h 06mAlaska Airlines
Deal found 12/14$525
This Delta deal was found by Cheapflights users on 12/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2512:34 pmOAK - ORD
1 stop7h 02mDelta
Thu 1/17:25 amORD - OAK
1 stop17h 22mDelta
Deal found 12/14$530

Find flight deals from Oakland to O'Hare Intl

Discover tips and strategies to find the most affordable flight options for your journey from Oakland (OAK) to O'Hare Intl (ORD). 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 December 15, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$256
(Kiwi.com)

One-way from

$119
(Delta)

Popular in

October

Cheapest in

July

Average price

$451
Provider with most accurate pricing for Oakland-Chicago O'Hare Intl flight deals.
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Provider most trusted by Cheapflights users for Oakland-Chicago O'Hare Intl flights.
Search Deals
From Oakland to Chicago O'Hare Intl
Search Deals
One-way flight from Oakland to Chicago O'Hare Intl
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($72 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Oakland to O'Hare Intl 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 December 15, 2025.
Use the filters below to find and compare flights from Oakland to Chicago O'Hare Intl Airport that are best for you.

Fly from

Oakland

Fly to

O'Hare Intl

Route

Depart

Return

Price

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 3/3

6:15 am-4:33 pm

1 stop8h 18m

Chicago O'Hare Intl

Wed 3/4

3:54 pm-10:49 pm

1 stop8h 55m

$277

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sat 1/10

7:00 am-10:35 pm

2 stops13h 35m

Chicago O'Hare Intl

Sat 1/17

1:00 pm-7:20 pm

1 stop8h 20m

$279

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 1/27

5:55 am-1:38 pm

1 stop5h 43m

Chicago O'Hare Intl

Tue 2/3

2:50 pm-11:53 pm

2 stops11h 03m

$280

OaklandChicago

OAK - ORD

OAKORD

Oakland

Fri 3/6

6:15 am-11:56 pm

1 stop15h 41m

Chicago O'Hare Intl

Mon 3/9

5:29 pm-4:37 pm

1 stop25h 08m

$283

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 1/8

5:17 pm-11:50 pm

1 stop28h 33m

Chicago O'Hare Intl

Mon 1/12

8:00 am-11:03 am

1 stop29h 03m

$283

OaklandChicago

OAK - ORD

OAKORD

Oakland

Fri 1/30

8:10 am-2:38 pm

1 stop28h 28m

Chicago O'Hare Intl

Mon 2/2

6:06 pm-4:23 pm

1 stop24h 17m

$283

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 1/15

5:17 pm-11:50 pm

1 stop28h 33m

Chicago O'Hare Intl

Tue 1/20

8:00 am-9:46 am

2 stops27h 46m

$288

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sun 2/8

5:17 pm-11:50 pm

1 stop28h 33m

Chicago O'Hare Intl

Fri 2/13

2:07 pm-9:24 am

1 stop21h 17m

$290

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 3/12

6:15 am-4:33 pm

1 stop8h 18m

Chicago O'Hare Intl

Mon 3/16

5:29 pm-9:14 am

1 stop17h 45m

$298

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 1/8

5:17 pm-11:50 pm

1 stop28h 33m

Chicago O'Hare Intl

Sun 1/11

3:35 pm-4:23 pm

1 stop26h 48m

$323

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/14

Showing 1-10 of 23 results
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Compare providers for flights from Oakland to O'Hare Intl

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 Oakland to O'Hare Intl in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
MytripPrice 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 Oakland, California-Chicago O'Hare Intl Airport flights, users find the pricing of Mytrip to be most consistent on Cheapflights vs. Mytrip Users can find the same prices on Oakland, California-Chicago O'Hare Intl Airport flight deals on Cheapflights vs. Mytrip >95% of the time. Price accuracy is based on data collected from Oakland, California-Chicago O'Hare Intl Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Oakland, California-Chicago O'Hare Intl Airport flights, Cheapflights users trust Mytrip the most. Mytrip 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 Oakland, California-Chicago O'Hare Intl Airport 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 Oakland to O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from Oakland 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 Oakland to Chicago O'Hare Intl Airport

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

Currently, December is the cheapest month in which you can book a flight from Oakland, California to Chicago O'Hare Intl Airport (average of $107). Flying from Oakland, California to Chicago O'Hare Intl Airport in November is currently the most expensive (average of $257). 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.

What is the cheapest time of day to fly from OAK to ORD?

Find hourly flight availability from Oakland to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 15, 2025.

It’s typically best to fly out from Oakland, California to Chicago O'Hare Intl Airport in the afternoon. Doing so could potentially save you 20% on the flight price compared to flying in the evening, which is usually more expensive.

Reviews of airlines servicing O'Hare Intl

Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated December 15, 2025.
Read reviews from past customers who have flown Alaska Airlines, Southwest, and United Airlines from Oakland to Chicago O'Hare Intl Airport. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
11,452 reviews

Overall

8.0

Boarding

8.1

Food

7.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Alaska Airlines
8.0
Very good
11,452 reviews
Alaska Airlines
8.0
Very good
11,452 reviews

Overall

8.0

Boarding

8.1

Food

7.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Southwest
7.9
Good
4,249 reviews
Alaska Airlines
8.0
Very good
11,452 reviews

Overall

8.0

Boarding

8.1

Food

7.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
United Airlines
7.4
Good
9,092 reviews
Alaska Airlines
8.0
Very good
11,452 reviews

Overall

8.0

Boarding

8.1

Food

7.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Spirit Airlines
6.3
Okay
8,188 reviews
Alaska Airlines
8.0
Very good
11,452 reviews

Overall

8.0

Boarding

8.1

Food

7.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.

Related info for your journey

Find useful and relevant information for your journey from Oakland to O'Hare Intl. 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 from for flights from Oakland to Chicago O'Hare Intl?

    Oakland (OAK), located 7.0 mi from the city center, is the airport you fly out of when you book flights from Oakland to Chicago O'Hare Intl. 4 airlines have flights from Oakland to Chicago O'Hare Intl on a regular basis. Booking flights from Oakland to Chicago O'Hare Intl should not be difficult; the airport handles an average of 0 outbound flights to Chicago O'Hare Intl per day.

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

    Airlines like Alaska Airlines, Southwest, and Delta fly from Oakland, California to Chicago O'Hare Intl Airport in about 5h 43m. The time it takes to get you to your destination can typically vary by up to 7h 52m. The distance between Oakland, California and Chicago O'Hare Intl Airport is about 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 Oakland, California to Chicago O'Hare Intl Airport round-trip?

    Spirit Airlines, at $100, was found to be the cheapest airline from Oakland, California to Chicago O'Hare Intl Airport.Alternate airlines to your destination round-trip include United Airlines and Alaska Airlines. Users have found that Spirit Airlines is 74% cheaper than the other options available to this destination.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Oakland to O'Hare Intl 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 Oakland, California to Chicago O'Hare Intl Airport?

    Currently, December is the cheapest month in which you can book a flight from Oakland, California to Chicago O'Hare Intl Airport (average of $107). Flying from Oakland, California to Chicago O'Hare Intl Airport in November is currently the most expensive (average of $257). 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

Traveling to a place near Chicago O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Schaumburg
Rosemont
Gurnee
Elgin
Naperville
Hoffman Estates
Beloit
Delavan
Oak Brook
Downers Grove
Des Plaines
Elk Grove Village
Skokie
Lake Geneva
Bridgeview
Warrenville
Waukegan
Aurora
Kenosha
Evanston

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Alternative routes for Oakland to O'Hare Intl

See prices for flight routes from nearby airports that may be better suited for you.
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Burbank to Midway flights
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Los Angeles to Rockford flights
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Fresno to Midway flights
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San Luis Obispo to O'Hare Intl flights
Medford to O'Hare Intl flights
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San Diego to Rockford flights
Arcata to O'Hare Intl flights
Redding to O'Hare Intl flights
Medford to Midway flights
Santa Rosa to O'Hare Intl flights
Tijuana to Midway flights
Yuma to O'Hare Intl flights
Bakersfield to Midway flights
Sacramento to Rockford flights
Ontario to Rockford flights
Tijuana to O'Hare Intl flights
San Jose to Rockford flights
Oakland to Rockford flights

Top 4 airlines flying from Oakland to O'Hare Intl

Discover the top 4 airlines that operate flights from Oakland to O'Hare Intl. 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 December 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$108Average$222FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$163Average$329FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$189Average$527FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$246Average$380FlexibilityNo cancel feeOn-time63%

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