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O'Hare Intl

$99+ 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 5/5. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — ORD
Apr 2 — Apr 91
Thu 4/2
Thu 4/9
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 3, 2026.

This Southwest deal was found by Cheapflights users on 2/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/281:50 pm
OAK
-
ORD
1 stop7h 05m
Southwest
Wed 4/296:15 am
ORD
-
OAK
1 stop8h 15m
Southwest
Deal found 2/26$230
This Southwest deal was found by Cheapflights users on 2/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/281:50 pm
OAK
-
ORD
1 stop7h 05m
Southwest
Sat 5/24:15 pm
ORD
-
OAK
1 stop6h 45m
Southwest
Deal found 2/26$245
This CheapOair deal was found by Cheapflights users on 2/26. 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.
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 2/26$259
This CheapOair deal was found by Cheapflights users on 2/26. 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.
Mon 5/186:02 am
OAK
-
ORD
1 stop15h 53m
Alaska Airlines
Tue 5/199:00 am
ORD
-
OAK
1 stop11h 21m
Alaska Airlines
Deal found 2/26$266
This Delta deal was found by Cheapflights users on 3/1. 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 3/3112:35 pm
OAK
-
ORD
1 stop6h 59m
Delta
Tue 4/78:55 am
ORD
-
OAK
2 stops9h 05m
Delta
Deal found 3/1$270
This CheapOair deal was found by Cheapflights users on 2/26. 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.
Mon 4/276:20 am
OAK
-
ORD
1 stop15h 39m
Alaska Airlines
Wed 4/296:00 am
ORD
-
OAK
1 stop9h 15m
Alaska Airlines
Deal found 2/26$271
This Alaska Airlines deal was found by Cheapflights users on 3/2. 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 4/282:09 pm
OAK
-
ORD
1 stop7h 50m
Alaska Airlines
Mon 5/46:00 am
ORD
-
OAK
1 stop29h 13m
Alaska Airlines
Deal found 3/2$274
This Southwest deal was found by Cheapflights users on 2/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/272:00 pm
OAK
-
ORD
2 stops7h 55m
Southwest
Wed 4/296:15 am
ORD
-
OAK
1 stop8h 15m
Southwest
Deal found 2/26$275

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 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$230
(Southwest)

One-way from

$99
(Southwest)

Popular in

October

Cheapest in

July

Average price

$508
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. 13% potential increase in price ($63 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 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 3, 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

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 4/22

7:19 pm-1:13 pm

1 stop15h 54m

Chicago O'Hare Intl

Sat 4/25

8:50 am-2:38 pm

1 stop7h 48m

$265

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 3/31

12:35 pm-9:34 pm

1 stop6h 59m

Chicago O'Hare Intl

Thu 4/2

6:15 am-11:46 pm

2 stops19h 31m

$345

OaklandChicago

OAK - ORD

OAKORD

Oakland

Mon 3/30

5:00 am-1:15 pm

1 stop6h 15m

Chicago O'Hare Intl

Mon 4/6

6:15 am-3:00 pm

2 stops10h 45m

$348

OaklandChicago

OAK - ORD

OAKORD

Oakland

Fri 4/3

5:00 am-1:15 pm

1 stop6h 15m

Chicago O'Hare Intl

Mon 4/6

3:05 pm-9:25 pm

1 stop8h 20m

$348

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 4/15

6:40 pm-6:39 am

1 stop9h 59m

Chicago O'Hare Intl

Thu 4/16

7:24 pm-11:43 pm

1 stop30h 19m

$349

OaklandChicago

OAK - ORD

OAKORD

Oakland

Fri 5/8

6:20 am-4:56 pm

1 stop8h 36m

Chicago O'Hare Intl

Sun 5/10

8:50 am-10:17 am

1 stop27h 27m

$388

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 4/1

7:00 am-11:59 pm

1 stop14h 59m

Chicago O'Hare Intl

Mon 4/6

7:24 pm-11:43 pm

1 stop30h 19m

$393

OaklandChicago

OAK - ORD

OAKORD

Oakland

Fri 4/10

8:10 pm-1:13 pm

1 stop15h 03m

Chicago O'Hare Intl

Thu 4/16

6:00 am-11:43 pm

1 stop19h 43m

$422

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 5/21

7:15 am-6:50 pm

2 stops9h 35m

Chicago O'Hare Intl

Sun 5/24

6:15 am-2:40 pm

2 stops10h 25m

$476

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sat 3/7

12:40 pm-9:52 pm

1 stop7h 12m

Chicago O'Hare Intl

Mon 3/9

7:10 pm-11:46 pm

1 stop6h 36m

$479

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/2

Showing 1-10 of 23 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 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 $123). 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 3, 2026.
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
11,977 reviews

Overall

8.0

Food

7.1

Entertainment

7.0

Comfort

7.8

Boarding

8.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Alaska Airlines
8.0
Very good
11,977 reviews
Alaska Airlines
8.0
Very good
11,977 reviews

Overall

8.0

Food

7.1

Entertainment

7.0

Comfort

7.8

Boarding

8.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Southwest
8.0
Very good
4,307 reviews
Alaska Airlines
8.0
Very good
11,977 reviews

Overall

8.0

Food

7.1

Entertainment

7.0

Comfort

7.8

Boarding

8.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
United Airlines
7.4
Good
9,375 reviews
Alaska Airlines
8.0
Very good
11,977 reviews

Overall

8.0

Food

7.1

Entertainment

7.0

Comfort

7.8

Boarding

8.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Spirit Airlines
6.3
Okay
8,486 reviews
Alaska Airlines
8.0
Very good
11,977 reviews

Overall

8.0

Food

7.1

Entertainment

7.0

Comfort

7.8

Boarding

8.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading

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 15m. The time it takes to get you to your destination can typically vary by up to 9h 39m. 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 73% 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 $123). 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
Naperville
Gurnee
Hoffman Estates
Beloit
Delavan
Des Plaines
Elgin
Downers Grove
Lake Geneva
Elk Grove Village
Skokie
Oak Brook
South Holland
Libertyville
Oakbrook Terrace
Waukegan
Warrenville
Bridgeview

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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 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$108Average$222FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$163Average$356FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$237Average$532FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$246Average$384FlexibilityNo cancel feeOn-time63%

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