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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 4/25. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — ORD
Feb 27 — Mar 61
Fri 2/27
Fri 3/6
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 January 28, 2026.

This Alaska Airlines deal was found by Cheapflights users on 1/26. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/137:00 am
OAK
-
ORD
1 stop9h 46m
Alaska Airlines
Wed 5/203:43 pm
ORD
-
OAK
1 stop9h 54m
Alaska Airlines
Deal found 1/26$237
This Alaska Airlines deal was found by Cheapflights users on 1/26. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/122:09 pm
OAK
-
ORD
1 stop7h 50m
Alaska Airlines
Tue 5/193:43 pm
ORD
-
OAK
1 stop9h 54m
Alaska Airlines
Deal found 1/26$240
This Southwest deal was found by Cheapflights users on 1/26. 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.
Wed 3/47:50 am
OAK
-
ORD
2 stops12h 45m
Southwest
Tue 3/107:00 am
ORD
-
OAK
1 stop8h 15m
Southwest
Deal found 1/26$242
This CheapOair deal was found by Cheapflights users on 1/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/127:19 pm
OAK
-
ORD
1 stop21h 27m
Alaska Airlines
Wed 5/203:43 pm
ORD
-
OAK
1 stop9h 54m
Alaska Airlines
Deal found 1/27$243
This CheapOair deal was found by Cheapflights users on 1/26. 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.
Wed 4/292:09 pm
OAK
-
ORD
1 stop7h 50m
Alaska Airlines
Mon 5/47:59 pm
ORD
-
OAK
1 stop20h 39m
Alaska Airlines
Deal found 1/26$250
This Alaska Airlines deal was found by Cheapflights users on 1/26. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/163:12 pm
OAK
-
ORD
1 stop6h 29m
Alaska Airlines
Wed 5/203:43 pm
ORD
-
OAK
1 stop9h 54m
Alaska Airlines
Deal found 1/26$253
This CheapOair deal was found by Cheapflights users on 1/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/286:15 am
OAK
-
ORD
1 stop8h 18m
Alaska Airlines
Sat 3/77:00 am
ORD
-
OAK
1 stop11h 37m
Alaska Airlines
Deal found 1/27$257
This Alaska Airlines deal was found by Cheapflights users on 1/27. 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.
Wed 4/222:09 pm
OAK
-
ORD
1 stop7h 50m
Alaska Airlines
Thu 4/307:59 pm
ORD
-
OAK
1 stop24h 16m
Alaska Airlines
Deal found 1/27$260
This Alaska Airlines deal was found by Cheapflights users on 1/26. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/137:00 am
OAK
-
ORD
1 stop9h 46m
Alaska Airlines
Mon 5/187:59 pm
ORD
-
OAK
1 stop15h 50m
Alaska Airlines
Deal found 1/26$263
This CheapOair deal was found by Cheapflights users on 1/25. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/156:40 pm
OAK
-
ORD
1 stop9h 59m
Alaska Airlines
Sat 4/186:00 am
ORD
-
OAK
1 stop13h 46m
Alaska Airlines
Deal found 1/25$267
This CheapOair deal was found by Cheapflights users on 1/26. 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.
Wed 2/256:15 am
OAK
-
ORD
1 stop8h 18m
Alaska Airlines
Wed 3/47:00 am
ORD
-
OAK
1 stop11h 37m
Alaska Airlines
Deal found 1/26$268
This Alaska Airlines deal was found by Cheapflights users on 1/27. 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.
Tue 2/246:15 am
OAK
-
ORD
1 stop15h 41m
Alaska Airlines
Wed 2/253:54 pm
ORD
-
OAK
1 stop8h 55m
Alaska Airlines
Deal found 1/27$270

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 January 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$237
(Alaska Airlines)

One-way from

$119
(Delta)

Popular in

October

Cheapest in

February

Average price

$453
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 ($73 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 January 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 January 28, 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

Oakland

Fly to

O'Hare Intl

Route

Depart

Return

Price

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 5/12

2:09 pm-11:59 pm

1 stop7h 50m

Chicago O'Hare Intl

Tue 5/19

3:43 pm-11:37 pm

1 stop9h 54m

$240

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 2/24

6:15 am-4:33 pm

1 stop8h 18m

Chicago O'Hare Intl

Wed 2/25

7:00 am-4:37 pm

1 stop11h 37m

$260

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 4/22

6:46 am-7:03 pm

1 stop10h 17m

Chicago O'Hare Intl

Thu 4/30

3:52 pm-10:23 pm

1 stop8h 31m

$268

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 2/25

4:59 pm-8:38 am

2 stops13h 39m

Chicago O'Hare Intl

Wed 3/4

2:05 pm-11:51 pm

2 stops11h 46m

$279

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 2/25

8:30 pm-1:00 pm

2 stops14h 30m

Chicago O'Hare Intl

Fri 2/27

6:25 pm-12:10 am

1 stop7h 45m

$281

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 4/30

2:09 pm-11:59 pm

1 stop7h 50m

Chicago O'Hare Intl

Mon 5/4

7:59 pm-10:17 am

1 stop16h 18m

$285

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sat 5/16

1:15 pm-9:58 pm

1 stop6h 43m

Chicago O'Hare Intl

Sun 5/31

6:59 pm-11:49 pm

1 stop6h 50m

$289

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 5/13

7:00 am-6:46 pm

1 stop9h 46m

Chicago O'Hare Intl

Thu 5/21

3:43 pm-11:37 pm

1 stop9h 54m

$292

OaklandChicago

OAK - ORD

OAKORD

Oakland

Fri 5/1

6:55 pm-1:13 pm

1 stop16h 18m

Chicago O'Hare Intl

Mon 5/4

7:59 pm-10:17 am

1 stop16h 18m

$302

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 4/16

12:34 pm-9:18 pm

1 stop6h 44m

Chicago O'Hare Intl

Sun 4/19

7:12 pm-11:54 pm

1 stop6h 42m

$303

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 20 results
1
2

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 January.
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, October is the cheapest month in which you can book a flight from Oakland, California to Chicago O'Hare Intl Airport (average of $125). 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 January 28, 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
11,801 reviews

Boarding

8.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Crew

8.5

Food

7.1

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
11,801 reviews
Alaska Airlines
8.0
Very good
11,801 reviews

Boarding

8.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Crew

8.5

Food

7.1

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
4,268 reviews
Alaska Airlines
8.0
Very good
11,801 reviews

Boarding

8.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Crew

8.5

Food

7.1

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
9,209 reviews
Alaska Airlines
8.0
Very good
11,801 reviews

Boarding

8.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Crew

8.5

Food

7.1

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
8,387 reviews
Alaska Airlines
8.0
Very good
11,801 reviews

Boarding

8.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Crew

8.5

Food

7.1

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 7h 50m. The time it takes to get you to your destination can typically vary by up to 6h 40m. 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, October is the cheapest month in which you can book a flight from Oakland, California to Chicago O'Hare Intl Airport (average of $125). 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
Elgin
Hoffman Estates
Beloit
Delavan
Oak Brook
Des Plaines
Downers Grove
Elk Grove Village
Skokie
Libertyville
Lake Geneva
Waukegan
Bridgeview
Kenosha
Warrenville
Aurora

Browse thousands of different options on Cheapflights for your next trip

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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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Medford to Midway flights
Los Angeles to Rockford flights
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San Francisco to Rockford flights
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Tijuana to Midway flights
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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 January 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$108Average$220FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$163Average$359FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$189Average$532FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$246Average$386FlexibilityNo cancel feeOn-time63%

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