HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
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 5/26. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — ORD
May 30 — Jun 61
Sat 5/30
Sat 6/6
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Oakland to O'Hare Intl with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 April 30, 2026.

This Delta deal was found by Cheapflights users on 4/27. 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 6/912:33 pm
OAK
-
ORD
1 stop7h 24m
Delta
Thu 7/27:45 am
ORD
-
OAK
1 stop6h 08m
Delta
Deal found 4/27$306
This Delta deal was found by Cheapflights users on 4/28. 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 5/2612:28 pm
OAK
-
ORD
1 stop7h 22m
Delta
Wed 6/107:37 pm
ORD
-
OAK
1 stop6h 17m
Delta
Deal found 4/28$308
This Delta deal was found by Cheapflights users on 4/28. 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.
Wed 7/296:00 am
OAK
-
ORD
2 stops10h 29m
Delta
Wed 8/196:59 pm
ORD
-
OAK
1 stop6h 50m
Delta
Deal found 4/28$311
This Southwest deal was found by Cheapflights users on 4/29. 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 5/2711:10 am
OAK
-
ORD
2 stops9h 45m
Southwest
Wed 6/310:30 am
ORD
-
OAK
2 stops9h 45m
Southwest
Deal found 4/29$312
This Alaska Airlines deal was found by Cheapflights users on 4/28. 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 5/1910:29 am
OAK
-
ORD
1 stop6h 21m
Alaska Airlines
Wed 5/279:00 am
ORD
-
OAK
1 stop7h 14m
Alaska Airlines
Deal found 4/28$313
This Alaska Airlines deal was found by Cheapflights users on 4/27. 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 5/286:02 am
OAK
-
ORD
1 stop10h 48m
Alaska Airlines
Tue 6/99:00 am
ORD
-
OAK
1 stop16h 50m
Alaska Airlines
Deal found 4/27$314
This Delta deal was found by Cheapflights users on 4/29. 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 6/912:33 pm
OAK
-
ORD
1 stop7h 24m
Delta
Fri 6/197:37 pm
ORD
-
OAK
1 stop6h 17m
Delta
Deal found 4/29$315
This Delta deal was found by Cheapflights users on 4/28. 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.
Wed 7/296:00 am
OAK
-
ORD
2 stops10h 29m
Delta
Tue 8/1811:30 am
ORD
-
OAK
2 stops14h 19m
Delta
Deal found 4/28$316
This lol.travel deal was found by Cheapflights users on 4/26. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/256:02 am
OAK
-
ORD
1 stop29h 12m
Alaska Airlines
Tue 6/29:00 am
ORD
-
OAK
1 stop7h 14m
Alaska Airlines
Deal found 4/26$317
This CheapOair deal was found by Cheapflights users on 4/26. 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 9/811:55 am
OAK
-
ORD
1 stop9h 46m
Alaska Airlines
Tue 9/227:59 pm
ORD
-
OAK
1 stop16h 45m
Alaska Airlines
Deal found 4/26$319
This Alaska Airlines deal was found by Cheapflights users on 4/25. 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 6/42:58 pm
OAK
-
ORD
1 stop6h 57m
Alaska Airlines
Sat 6/63:28 pm
ORD
-
OAK
1 stop10h 31m
Alaska Airlines
Deal found 4/25$320
This CheapOair deal was found by Cheapflights users on 4/26. 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.
Sun 5/247:00 am
OAK
-
ORD
1 stop7h 48m
Alaska Airlines
Wed 5/279:00 am
ORD
-
OAK
1 stop7h 14m
Alaska Airlines
Deal found 4/26$323

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 April 30, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$306
(Delta)

One-way from

$129
(Delta)

Popular in

October

Cheapest in

July

Average price

$457
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. 15% potential increase in price ($71 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 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 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 April 30, 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 8/11

5:05 pm-8:34 am

2 stops13h 29m

Chicago O'Hare Intl

Tue 8/18

1:35 pm-11:49 pm

2 stops12h 14m

$361

OaklandChicago

OAK - ORD

OAKORD

Oakland

Fri 8/7

6:49 am-6:57 pm

1 stop10h 08m

Chicago O'Hare Intl

Mon 8/10

8:05 pm-9:26 am

1 stop15h 21m

$364

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 5/28

6:02 am-6:50 pm

1 stop10h 48m

Chicago O'Hare Intl

Sun 5/31

7:59 pm-9:45 am

1 stop15h 46m

$391

OaklandChicago

OAK - ORD

OAKORD

Oakland

Mon 7/27

12:30 pm-9:48 pm

1 stop7h 18m

Chicago O'Hare Intl

Sat 8/8

8:27 am-4:22 pm

2 stops9h 55m

$392

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 6/2

12:28 pm-9:50 pm

1 stop7h 22m

Chicago O'Hare Intl

Sat 6/6

1:44 pm-10:34 pm

2 stops10h 50m

$403

OaklandChicago

OAK - ORD

OAKORD

Oakland

Fri 8/7

6:00 am-6:29 pm

2 stops10h 29m

Chicago O'Hare Intl

Mon 8/10

11:30 am-11:49 pm

2 stops14h 19m

$406

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sun 8/30

6:49 am-7:03 pm

1 stop10h 14m

Chicago O'Hare Intl

Sun 9/6

7:00 am-12:49 pm

1 stop7h 49m

$427

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sat 5/23

6:02 am-6:50 pm

1 stop10h 48m

Chicago O'Hare Intl

Sun 5/24

9:00 am-2:14 pm

1 stop7h 14m

$444

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 6/9

5:03 pm-8:35 am

2 stops13h 32m

Chicago O'Hare Intl

Tue 6/16

6:30 am-11:54 pm

2 stops19h 24m

$455

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 7/9

12:30 pm-9:48 pm

1 stop7h 18m

Chicago O'Hare Intl

Mon 7/13

5:54 pm-11:50 pm

2 stops7h 56m

$462

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

Showing 1-10 of 21 resultsSorted by cheapest first
1
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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy2 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, July is the cheapest month in which you can book a flight from Oakland, California to Chicago O'Hare Intl Airport (average of $232). Flying from Oakland, California to Chicago O'Hare Intl Airport in October is currently the most expensive (average of $527). 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 Oakland, California to Chicago O'Hare Intl Airport?

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 April 30, 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
4,317 reviews

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

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
4,317 reviews
Southwest
8.0
Very good
4,317 reviews

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

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
12,318 reviews
Southwest
8.0
Very good
4,317 reviews

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

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
9,678 reviews
Southwest
8.0
Very good
4,317 reviews

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

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
8,638 reviews
Southwest
8.0
Very good
4,317 reviews

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

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 Delta and Alaska Airlines fly from Oakland, California to Chicago O'Hare Intl Airport in about 10h 08m. The time it takes to get you to your destination can typically vary by up to 3h 21m. 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?

    United Airlines, at $163, was found to be the cheapest airline from Oakland, California to Chicago O'Hare Intl Airport.Alternate airlines to your destination round-trip include Spirit Airlines and Alaska Airlines. Users have found that United Airlines is 58% 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, July is the cheapest month in which you can book a flight from Oakland, California to Chicago O'Hare Intl Airport (average of $232). Flying from Oakland, California to Chicago O'Hare Intl Airport in October is currently the most expensive (average of $527). 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
Rosemont
Schaumburg
Naperville
Lake Geneva
Gurnee
Delavan
Downers Grove
Oakbrook Terrace
Benton Harbor
Hoffman Estates
Des Plaines
Oak Brook
South Holland
Libertyville
Warrenville
Elk Grove Village
Bridgeview
Great Lakes
Lansing
Arlington Heights

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 April 30, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$163Average$359FlexibilityNo cancel feeOn-time69%
Spirit AirlinesCheapest$172Average$222FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$237Average$532FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$246Average$380FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.