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O'Hare Intl

$129+ 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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — ORD
Apr 16 — Apr 231
Thu 4/16
Thu 4/23
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 March 17, 2026.

This Alaska Airlines deal was found by Cheapflights users on 3/11. 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.
Tue 4/286:46 am
OAK
-
ORD
1 stop10h 17m
Alaska Airlines
Wed 4/293:52 pm
ORD
-
OAK
1 stop8h 31m
Alaska Airlines
Deal found 3/11$217
This CheapOair deal was found by Cheapflights users on 3/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/22:09 pm
OAK
-
ORD
1 stop7h 50m
Alaska Airlines
Sat 5/93:52 pm
ORD
-
OAK
1 stop20h 25m
Alaska Airlines
Deal found 3/11$253
This Southwest deal was found by Cheapflights users on 3/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/61:50 pm
OAK
-
ORD
1 stop7h 05m
Southwest
Tue 5/124:50 pm
ORD
-
OAK
1 stop7h 45m
Southwest
Deal found 3/13$257
This CheapOair deal was found by Cheapflights users on 3/12. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/22:09 pm
OAK
-
ORD
1 stop7h 50m
Alaska Airlines
Tue 5/56:00 am
ORD
-
OAK
1 stop9h 15m
Alaska Airlines
Deal found 3/12$261
This Southwest deal was found by Cheapflights users on 3/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/81:50 pm
OAK
-
ORD
1 stop7h 05m
Southwest
Wed 4/1511:55 am
ORD
-
OAK
2 stops10h 25m
Southwest
Deal found 3/11$262
This Southwest deal was found by Cheapflights users on 3/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1512:25 pm
OAK
-
ORD
2 stops8h 30m
Southwest
Wed 4/224:50 pm
ORD
-
OAK
1 stop7h 45m
Southwest
Deal found 3/13$270
This Expedia deal was found by Cheapflights users on 3/12. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/66:20 am
OAK
-
ORD
1 stop15h 39m
Alaska Airlines
Mon 5/117:59 pm
ORD
-
OAK
1 stop16h 18m
Alaska Airlines
Deal found 3/12$273
This Alaska Airlines deal was found by Cheapflights users on 3/15. 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.
Wed 4/226:20 am
OAK
-
ORD
1 stop8h 36m
Alaska Airlines
Tue 4/286:00 am
ORD
-
OAK
2 stops18h 23m
Alaska Airlines
Deal found 3/15$279
This Southwest deal was found by Cheapflights users on 3/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/273:45 pm
OAK
-
ORD
1 stop6h 10m
Southwest
Wed 5/1310:30 am
ORD
-
OAK
2 stops9h 45m
Southwest
Deal found 3/16$280

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 March 17, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$217
(Alaska Airlines)

One-way from

$129
(Southwest)

Popular in

March

Cheapest in

July

Average price

$530
Provider with most accurate pricing for Oakland-Chicago O'Hare Intl flight deals.
Search Deals
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. 6% potential increase in price ($28 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals

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 March 17, 2026.
Use the filters below to find and compare flights from Oakland to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 4/28

9:53 am-7:52 pm

1 stop7h 59m

Chicago O'Hare Intl

Wed 4/29

3:52 pm-10:23 pm

1 stop8h 31m

$265

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 4/15

12:34 pm-9:18 pm

1 stop6h 44m

Chicago O'Hare Intl

Fri 4/17

7:10 pm-11:54 pm

1 stop6h 44m

$285
Quickest round-trip

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 4/15

3:00 pm-11:55 pm

1 stop6h 55m

Chicago O'Hare Intl

Fri 4/17

6:15 pm-10:35 pm

1 stop6h 20m

$291

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 5/27

1:50 pm-10:55 pm

1 stop7h 05m

Chicago O'Hare Intl

Sun 5/31

7:15 pm-12:45 am

1 stop7h 30m

$356

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 7/30

7:35 am-5:15 pm

1 stop7h 40m

Chicago O'Hare Intl

Wed 8/5

7:10 am-2:20 pm

2 stops9h 10m

$369

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 5/6

11:10 am-10:55 pm

2 stops9h 45m

Chicago O'Hare Intl

Sun 5/10

6:15 am-12:50 pm

2 stops8h 35m

$372

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 7/15

5:05 pm-7:26 am

2 stops12h 21m

Chicago O'Hare Intl

Fri 7/17

6:59 pm-11:49 pm

1 stop6h 50m

$389

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sat 6/6

12:28 pm-9:50 pm

1 stop7h 22m

Chicago O'Hare Intl

Tue 6/9

1:35 pm-11:49 pm

2 stops12h 14m

$392

OaklandChicago

OAK - ORD

OAKORD

Oakland

Fri 4/24

12:10 pm-11:55 pm

2 stops9h 45m

Chicago O'Hare Intl

Mon 4/27

6:15 am-1:45 pm

2 stops9h 30m

$392

OaklandChicago

OAK - ORD

OAKORD

Oakland

Fri 4/10

2:00 pm-11:55 pm

2 stops7h 55m

Chicago O'Hare Intl

Thu 4/16

8:00 am-2:55 pm

2 stops8h 55m

$416

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/12

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

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 March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star

*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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Oakland, California-Chicago O'Hare Intl Airport flight deals on Cheapflights vs. FlightHub >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 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 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, April is the cheapest month in which you can book a flight from Oakland, California to Chicago O'Hare Intl Airport (average of $115). 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.

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 March 17, 2026.
Read reviews from past customers who have flown Southwest,Alaska Airlines, andUnited 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.
Southwest
8.0
Very good
4,319 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Southwest
8.0
Very good
4,319 reviews
Southwest
8.0
Very good
4,319 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Alaska Airlines
7.9
Good
12,052 reviews
Southwest
8.0
Very good
4,319 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
United Airlines
7.4
Good
9,431 reviews
Southwest
8.0
Very good
4,319 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Spirit Airlines
6.3
Okay
8,521 reviews
Southwest
8.0
Very good
4,319 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.

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, Delta, and Southwest fly from Oakland, California to Chicago O'Hare Intl Airport in about 6h 44m. The time it takes to get you to your destination can typically vary by up to 1h 15m. 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 $108, 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 72% 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, April is the cheapest month in which you can book a flight from Oakland, California to Chicago O'Hare Intl Airport (average of $115). 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
Naperville
Lake Geneva
Hoffman Estates
Delavan
Downers Grove
Des Plaines
Elgin
Oak Brook
South Holland
Elk Grove Village
Libertyville
Waukegan
Beloit
Warrenville
Oakbrook Terrace
Bridgeview
Great Lakes

Browse thousands of different options on Cheapflights for your next trip

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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 March 17, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$108Average$222FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$163Average$359FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$237Average$527FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$246Average$372FlexibilityNo cancel feeOn-time63%

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