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O'Hare Intl

$65+ 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 9/24. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — ORD
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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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 September 11, 2025.

Round-trip from

$152
(Booking.com)

One-way from

$65
(CheapOair)

Popular in

March

Cheapest in

February

Average price

$216
From Oakland to Chicago O'Hare Intl
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One-way flight from Oakland to Chicago O'Hare Intl
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Highest demand for flights based on searches. 11% potential increase in price ($43 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 September 11, 2025.

This Booking.com deal was found by Cheapflights users on 9/10. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2410:56 amOAK - ORD
2 stops8h 36mSpirit Airlines
Wed 10/111:15 amORD - OAK
1 stop14h 17mSpirit Airlines
Deal found 9/10$152
This Cheapflightsfares deal was found by Cheapflights users on 9/9. 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.
Fri 9/266:30 amOAK - ORD
1 stop13h 02mSpirit Airlines
Tue 9/3011:15 amORD - OAK
1 stop14h 17mSpirit Airlines
Deal found 9/9$166
This CheapOair deal was found by Cheapflights users on 9/9. 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 9/236:30 amOAK - ORD
1 stop13h 02mSpirit Airlines
Tue 9/3011:15 amORD - OAK
1 stop14h 17mSpirit Airlines
Deal found 9/9$176
This Cheapflightsfares deal was found by Cheapflights users on 9/9. 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 9/236:30 amOAK - ORD
1 stop13h 02mSpirit Airlines
Wed 10/111:15 amORD - OAK
1 stop14h 17mSpirit Airlines
Deal found 9/9$177
This Southwest deal was found by Cheapflights users on 9/9. 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.
Sat 10/113:25 pmOAK - ORD
1 stop5h 40mSouthwest
Sat 10/187:00 amORD - OAK
1 stop9h 00mSouthwest
Deal found 9/9$185
This CheapOair deal was found by Cheapflights users on 9/9. 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 9/276:30 amOAK - ORD
1 stop13h 02mSpirit Airlines
Tue 9/3011:15 amORD - OAK
1 stop14h 17mSpirit Airlines
Deal found 9/9$188
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1710:56 amOAK - ORD
2 stops32h 36mMultiple Airlines
Mon 9/229:54 pmORD - OAK
1 stop27h 38mMultiple Airlines
Deal found 9/9$189
This Expedia deal was found by Cheapflights users on 9/10. 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.
Thu 9/256:30 amOAK - ORD
1 stop13h 02mMultiple Airlines
Tue 10/76:00 amORD - OAK
1 stop20h 03mMultiple Airlines
Deal found 9/10$190
This Alaska Airlines deal was found by Cheapflights users on 9/9. 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 9/309:39 amOAK - ORD
1 stop10h 28mAlaska Airlines
Tue 10/76:00 amORD - OAK
1 stop30h 23mAlaska Airlines
Deal found 9/9$191

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 September 11, 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 10/29

2:49 pm-12:24 am

1 stop7h 35m

Chicago O'Hare Intl

Tue 11/4

8:00 am-1:55 pm

1 stop7h 55m

$191

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 10/28

6:30 am-12:24 am

1 stop15h 54m

Chicago O'Hare Intl

Wed 11/19

8:00 am-11:59 pm

1 stop17h 59m

$191

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 9/30

6:15 am-10:07 pm

1 stop13h 52m

Chicago O'Hare Intl

Sat 10/4

6:00 am-12:03 am

1 stop20h 03m

$205

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 11/4

5:40 am-3:25 pm

1 stop7h 45m

Chicago O'Hare Intl

Fri 11/7

4:25 pm-11:00 pm

1 stop8h 35m

$233

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 11/13

6:30 am-12:24 am

1 stop15h 54m

Chicago O'Hare Intl

Mon 11/17

6:00 am-11:59 pm

1 stop19h 59m

$238

OaklandChicago

OAK - ORD

OAKORD

Oakland

Mon 10/20

6:40 am-11:59 pm

1 stop15h 19m

Chicago O'Hare Intl

Sat 10/25

6:00 am-12:03 am

1 stop20h 03m

$250

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 11/4

5:40 am-3:25 pm

1 stop7h 45m

Chicago O'Hare Intl

Sat 11/8

7:15 am-12:20 pm

1 stop7h 05m

$252

OaklandChicago

OAK - ORD

OAKORD

Oakland

Mon 10/27

6:30 am-6:22 am

1 stop21h 52m

Chicago O'Hare Intl

Wed 11/19

2:05 pm-11:59 pm

2 stops11h 54m

$253

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 10/23

6:40 am-6:24 am

1 stop21h 44m

Chicago O'Hare Intl

Mon 10/27

6:00 am-11:59 pm

1 stop19h 59m

$256

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sat 11/8

12:30 pm-9:43 pm

1 stop7h 13m

Chicago O'Hare Intl

Tue 11/11

7:33 am-11:48 am

1 stop6h 15m

$257

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 21 results
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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, August is the cheapest month in which you can book a flight from Oakland, California to Chicago O'Hare Intl Airport (average of $245). Flying from Oakland, California to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $321). 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 September 11, 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 21% 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 September 11, 2025.
Read reviews from past customers who have flown Southwest, United Airlines, and Spirit 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
4,248 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
United Airlines
7.4
Good
8,937 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Spirit Airlines
6.3
Okay
8,023 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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. 3 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 Southwest fly from Oakland, California to Chicago O'Hare Intl Airport in about 7h 35m. The time it takes to get you to your destination can typically vary by up to 10m. 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 Southwest. Users have found that Spirit Airlines is 68% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from Oakland, California to Chicago O'Hare Intl Airport one-way?

    The cheapest airlines for a one-way flight from Oakland, California to Chicago O'Hare Intl Airport are Southwest ($93), Alaska Airlines ($95), and Hawaiian Airlines ($95).

  • 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, August is the cheapest month in which you can book a flight from Oakland, California to Chicago O'Hare Intl Airport (average of $245). Flying from Oakland, California to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $321). 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
Gurnee
Hoffman Estates
Des Plaines
Elgin
Arlington Heights
Beloit
Racine
Rockford
Orland Park
Oak Brook
Downers Grove
Naperville
Elk Grove Village
Evanston
Merrillville
Bridgeview
Warrenville

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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 3 airlines flying from Oakland to O'Hare Intl

Discover the top 3 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$108Average$221FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$163Average$287FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$242Average$388FlexibilityNo cancel feeOn-time63%

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