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O'Hare Intl

$125+ 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 2/15. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — ORD
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Find 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 October 30, 2025.

This SmartFares deal was found by Cheapflights users on 10/30. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/411:21 amOAK - ORD
1 stop9h 09mAlaska Airlines
Wed 12/105:51 pmORD - OAK
1 stop8h 08mAlaska Airlines
Deal found 10/30$296
This Travelocity deal was found by Cheapflights users on 10/28. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/196:30 amOAK - ORD
1 stop15h 54mAlaska Airlines
Tue 12/28:59 pmORD - OAK
2 stops18h 33mAlaska Airlines
Deal found 10/28$298
This Cheapflightsfares deal was found by Cheapflights users on 10/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/42:31 pmOAK - ORD
1 stop7h 28mAlaska Airlines
Thu 12/115:51 pmORD - OAK
1 stop8h 08mAlaska Airlines
Deal found 10/29$299
This KAYAK deal was found by Cheapflights users on 10/29. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/52:31 pmOAK - ORD
1 stop7h 28mAlaska Airlines
Mon 12/86:00 amORD - OAK
1 stop9h 32mAlaska Airlines
Deal found 10/29$300
This Alaska Airlines deal was found by Cheapflights users on 10/29. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/112:31 pmOAK - ORD
1 stop7h 28mAlaska Airlines
Sat 12/138:00 amORD - OAK
1 stop28h 41mAlaska Airlines
Deal found 10/29$302
This Cheapflightsfares deal was found by Cheapflights users on 10/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/96:40 amOAK - ORD
2 stops11h 14mAlaska Airlines
Thu 12/115:51 pmORD - OAK
1 stop8h 08mAlaska Airlines
Deal found 10/29$305
This Alaska Airlines deal was found by Cheapflights users on 10/29. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/92:31 pmOAK - ORD
2 stops21h 38mAlaska Airlines
Sun 12/146:00 amORD - OAK
1 stop19h 59mAlaska Airlines
Deal found 10/29$308
This Alaska Airlines deal was found by Cheapflights users on 10/30. 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 12/159:26 amOAK - ORD
1 stop25h 43mAlaska Airlines
Tue 12/165:51 pmORD - OAK
1 stop8h 08mAlaska Airlines
Deal found 10/30$309
This KAYAK deal was found by Cheapflights users on 10/29. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/122:49 pmOAK - ORD
1 stop7h 35mAlaska Airlines
Wed 11/198:00 amORD - OAK
1 stop7h 55mAlaska Airlines
Deal found 10/29$310
This Cheapflightsfares deal was found by Cheapflights users on 10/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/62:31 pmOAK - ORD
1 stop7h 28mAlaska Airlines
Tue 12/95:51 pmORD - OAK
1 stop8h 08mAlaska Airlines
Deal found 10/30$314

Cheap 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 October 30, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$260
(Travelocity)

One-way from

$125
(Netflights)

Popular in

March

Cheapest in

February

Average price

$320
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.
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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. 8% potential increase in price ($33 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 30, 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

Wed 12/10

11:21 am-10:30 pm

1 stop9h 09m

Chicago O'Hare Intl

Tue 12/16

2:05 pm-8:46 am

1 stop20h 41m

$309

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 12/11

6:40 am-4:55 pm

1 stop8h 15m

Chicago O'Hare Intl

Wed 12/17

5:51 pm-11:59 pm

1 stop8h 08m

$316

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sat 12/13

4:50 pm-8:42 am

2 stops13h 52m

Chicago O'Hare Intl

Wed 12/17

7:20 am-11:50 am

1 stop6h 30m

$323

OaklandChicago

OAK - ORD

OAKORD

Oakland

Mon 12/1

7:59 pm-5:01 am

1 stop7h 02m

Chicago O'Hare Intl

Thu 12/4

6:00 am-1:32 pm

1 stop9h 32m

$327

OaklandChicago

OAK - ORD

OAKORD

Oakland

Mon 12/1

7:59 pm-5:01 am

1 stop7h 02m

Chicago O'Hare Intl

Wed 12/3

8:00 am-11:59 pm

1 stop17h 59m

$330

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 11/12

2:49 pm-12:24 am

1 stop7h 35m

Chicago O'Hare Intl

Wed 11/19

8:00 am-11:59 pm

1 stop17h 59m

$330

OaklandChicago

OAK - ORD

OAKORD

Oakland

Mon 11/17

2:49 pm-12:24 am

1 stop7h 35m

Chicago O'Hare Intl

Wed 11/19

8:00 am-1:55 pm

1 stop7h 55m

$330

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sun 12/14

5:55 am-6:27 pm

2 stops10h 32m

Chicago O'Hare Intl

Wed 12/17

7:20 am-11:50 am

1 stop6h 30m

$333

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sun 12/14

2:31 pm-11:59 pm

1 stop7h 28m

Chicago O'Hare Intl

Tue 12/16

5:51 pm-11:59 pm

1 stop8h 08m

$361

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sun 12/14

2:31 pm-11:59 pm

1 stop7h 28m

Chicago O'Hare Intl

Wed 12/17

5:51 pm-11:59 pm

1 stop8h 08m

$361

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 21 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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
Kiwi.comPrice 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 $111). Flying from Oakland, California to Chicago O'Hare Intl Airport in November is currently the most expensive (average of $195). 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 October 30, 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 October 30, 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
11,219 reviews

Overall

8.0

Boarding

8.1

Food

7.1

Crew

8.5

Entertainment

7.0

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Alaska Airlines
8.0
Very good
11,219 reviews
Alaska Airlines
8.0
Very good
11,219 reviews

Overall

8.0

Boarding

8.1

Food

7.1

Crew

8.5

Entertainment

7.0

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Southwest
8.0
Very good
4,243 reviews
Alaska Airlines
8.0
Very good
11,219 reviews

Overall

8.0

Boarding

8.1

Food

7.1

Crew

8.5

Entertainment

7.0

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
United Airlines
7.4
Good
8,998 reviews
Alaska Airlines
8.0
Very good
11,219 reviews

Overall

8.0

Boarding

8.1

Food

7.1

Crew

8.5

Entertainment

7.0

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Spirit Airlines
6.3
Okay
8,116 reviews
Alaska Airlines
8.0
Very good
11,219 reviews

Overall

8.0

Boarding

8.1

Food

7.1

Crew

8.5

Entertainment

7.0

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.

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 and Delta fly from Oakland, California to Chicago O'Hare Intl Airport in about 9h 09m. The time it takes to get you to your destination can typically vary by up to 4h 43m. 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 69% 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 $111). Flying from Oakland, California to Chicago O'Hare Intl Airport in November is currently the most expensive (average of $195). 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
Skokie
Des Plaines
Gurnee
Hoffman Estates
Beloit
Elgin
Oak Brook
Elk Grove Village
Naperville
Racine
Downers Grove
Rockford
Orland Park
Merrillville
Bridgeview
Warrenville
Waukegan
Aurora

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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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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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$108Average$220FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$163Average$297FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$189Average$356FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$246Average$389FlexibilityNo cancel feeOn-time63%

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