HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Oakland

$84+ Cheap flights from Illinois to Oakland, CA (OAK)

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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — OAK
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Illinois to Oakland 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 Illinois to Oakland

Keep the following information in mind while searching for Illinois to Oakland flight deals. Data was last updated September 17, 2025.

Round-trip from

$229
(CheapOair)

One-way from

$84
(Cheapflightsfares)

Popular in

December

Cheapest in

July

Average price

$297

Good round-trip deal

$448 or less

Good one-way deal

$238 or less
From Illinois to Oakland
Search Deals
One-way flight from Illinois to Oakland
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($28 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals
Price to beat on a round-trip flight from Illinois to Oakland.
Search Deals
Price to beat on a one-way flight from Illinois to Oakland.
Search Deals

Find flight deals from Illinois to Oakland

Cheapest flights from Illinois to Oakland
Explore the most affordable flight options available from Illinois to Oakland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 9/3011:15 amORD - OAK
1 stop14h 17mSpirit Airlines
Wed 10/16:30 amOAK - ORD
1 stop13h 02mSpirit Airlines
Deal found 9/15$225
This CheapOair deal was found by Cheapflights users on 9/17. 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 10/111:15 amORD - OAK
1 stop14h 17mSpirit Airlines
Fri 10/36:30 amOAK - ORD
1 stop13h 06mSpirit Airlines
Deal found 9/17$229
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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.
Mon 9/296:05 pmORD - OAK
1 stop7h 27mSpirit Airlines
Wed 10/16:30 amOAK - ORD
1 stop13h 02mSpirit Airlines
Deal found 9/15$231
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/111:15 amORD - OAK
1 stop14h 17mMultiple Airlines
Wed 10/87:06 pmOAK - ORD
1 stop7h 55mMultiple Airlines
Deal found 9/14$233
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Tue 9/3011:15 amORD - OAK
1 stop14h 17mMultiple Airlines
Sat 10/410:56 amOAK - ORD
2 stops44h 41mMultiple Airlines
Deal found 9/14$236
This KAYAK deal was found by Cheapflights users on 9/17. 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 11/128:00 amORD - OAK
1 stop7h 55mAlaska Airlines
Mon 11/178:03 pmOAK - ORD
1 stop8h 19mAlaska Airlines
Deal found 9/17$259
This KAYAK deal was found by Cheapflights users on 9/16. 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.
Tue 10/288:00 amORD - OAK
1 stop7h 55mAlaska Airlines
Thu 10/3011:05 amOAK - ORD
1 stop8h 35mAlaska Airlines
Deal found 9/16$261
This CheapOair deal was found by Cheapflights users on 9/16. 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 9/2311:15 amORD - OAK
1 stop14h 17mSpirit Airlines
Thu 10/26:30 amOAK - ORD
1 stop13h 06mSpirit Airlines
Deal found 9/16$263
This Cheapflightsfares deal was found by Cheapflights users on 9/16. 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 10/215:59 pmORD - OAK
1 stop8h 04mAlaska Airlines
Tue 10/282:49 pmOAK - ORD
1 stop7h 35mAlaska Airlines
Deal found 9/16$272
This Southwest deal was found by Cheapflights users on 9/17. 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 11/54:05 pmMDW - OAK
Nonstop4h 35mSouthwest
Mon 11/105:25 amOAK - MDW
Nonstop4h 05mSouthwest
Deal found 9/17$287
This Southwest deal was found by Cheapflights users on 9/16. 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 10/77:10 amMDW - OAK
1 stop7h 40mSouthwest
Sat 10/111:20 pmOAK - MDW
1 stop7h 10mSouthwest
Deal found 9/16$307
This Southwest deal was found by Cheapflights users on 9/16. 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.
Thu 10/308:00 amMDW - OAK
1 stop6h 25mSouthwest
Mon 11/37:50 amOAK - MDW
1 stop7h 05mSouthwest
Deal found 9/16$317

Cheapflights Fare Finder

 
Customize your flight search to find flights from Illinois to Oakland 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 17, 2025.
Use the filters below to find and compare flights from Illinois to Oakland that are best for you.

Fly from

Illinois

Fly to

Oakland

Route

Depart

Return

Price

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Fri 11/14

3:25 pm-11:59 pm

1 stop10h 34m

Oakland

Sat 11/15

2:49 pm-12:24 am

1 stop7h 35m

$276

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Tue 3/10

2:05 pm-7:14 pm

1 stop7h 09m

Oakland

Wed 3/11

6:35 pm-5:04 am

1 stop8h 29m

$277

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Wed 11/5

12:05 pm-6:35 pm

1 stop8h 30m

Oakland

Mon 11/10

5:25 am-11:30 am

Nonstop4h 05m

$297

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Fri 11/14

5:53 pm-11:59 pm

1 stop8h 06m

Oakland

Sat 11/15

9:48 am-11:59 pm

2 stops12h 11m

$302

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Tue 10/14

5:25 pm-9:45 pm

1 stop6h 20m

Oakland

Sat 10/18

5:05 am-2:00 pm

1 stop6h 55m

$307

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Mon 12/15

5:15 pm-9:45 pm

1 stop6h 30m

Oakland

Tue 1/6

12:30 pm-7:55 pm

1 stop5h 25m

$307

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Wed 10/1

6:20 am-1:36 pm

1 stop9h 16m

Oakland

Wed 10/8

7:06 pm-5:01 am

1 stop7h 55m

$317

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Sat 11/8

8:30 am-3:15 pm

1 stop8h 45m

Oakland

Sun 11/16

5:25 am-11:30 am

Nonstop4h 05m

$320

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Mon 12/15

7:15 am-4:40 pm

2 stops11h 25m

Oakland

Tue 1/6

8:30 pm-1:30 pm

2 stops15h 00m

$323

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Wed 12/17

5:00 am-11:40 am

2 stops8h 40m

Oakland

Sat 12/27

5:10 am-11:15 am

Nonstop4h 05m

$323

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/17

Showing 1-10 of 60 results
1
2
3
...
6

Best time to book a flight from Illinois to Oakland

Have a flexible travel schedule? Discover the best time to fly to Oakland from Illinois 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 Illinois to Oakland

What is the cheapest month to book a flight from Illinois to Oakland, California?

Currently, April is the cheapest month in which you can book a flight from Illinois to Oakland, California (average of $183). Flying from Illinois to Oakland, California in November is currently the most expensive (average of $259). 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 IL to OAK?

Find hourly flight availability from Illinois to Oakland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 17, 2025.

When flying from Illinois to Oakland, California, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Related info for your journey

Find useful and relevant information for your journey from Illinois to Oakland. 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 into for flights to Oakland from Illinois?

    Oakland (OAK), located 7.0 mi from the city center, is the airport you fly into when you book flights from Illinois to Oakland.

  • How long is the flight from Illinois to Oakland, California?

    A quick flight from Illinois to Oakland, California can take about 7h 09m. Hawaiian Airlines provides one of the quickest options available for as low as $277. Illinois and Oakland, California are separated by a distance of 1830 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Illinois to Oakland, California one-way?

    One-way options have recently been found by users for as low as $138 on Alaska Airlines. Other airlines that offer cheap prices include Hawaiian Airlines from $138 and Delta from $144 one-way.

  • What are the most popular routes from Illinois to Oakland, California?

    While some choose either Chicago Midway - Oakland or Lambert-St Louis - Oakland, Chicago O'Hare Intl - Oakland is the most popular route from Illinois to Oakland, California.

  • Can I find deals for flights from Illinois to Oakland that include hotel bookings?

    Yes. In addition to deals on Illinois to Oakland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Illinois to Oakland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Illinois to Oakland.

  • Can I find deals for business class flights from Illinois to Oakland?

    Yes. Cheapflights offers flight deals from Illinois to Oakland 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 Illinois to Oakland, California?

    Currently, April is the cheapest month in which you can book a flight from Illinois to Oakland, California (average of $183). Flying from Illinois to Oakland, California in November is currently the most expensive (average of $259). 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

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.

Alternative routes for Illinois to Oakland

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to Los Angeles flights
John F Kennedy Intl to Las Vegas flights
Dallas/Fort Worth to Las Vegas flights
Seattle to Los Angeles flights
Newark to Las Vegas flights
John F Kennedy Intl to San Francisco flights
Seattle to Las Vegas flights
O'Hare Intl to Las Vegas flights
Newark to Los Angeles flights
Los Angeles to San Francisco flights
San Francisco to Las Vegas flights
Dallas/Fort Worth to Los Angeles flights
San Francisco to Los Angeles flights
Los Angeles to Las Vegas flights
Seattle to Ontario flights
O'Hare Intl to Los Angeles flights
LaGuardia to Los Angeles flights
Atlanta to Las Vegas flights
Hobby to Las Vegas flights
Newark to San Francisco flights
Santa Ana to Las Vegas flights
LaGuardia to Las Vegas flights
Boston to Las Vegas flights
Reagan-National to Los Angeles flights
Burbank to Las Vegas flights
Ontario to San Francisco flights
Denver to Las Vegas flights
Dulles Intl to Los Angeles flights
San Francisco to Ontario flights
Dulles Intl to Las Vegas flights
San Francisco to Santa Ana flights
Seattle to San Diego flights
Boston to Los Angeles flights
John F Kennedy Intl to Ontario flights
Minneapolis to Las Vegas flights
San Jose to Los Angeles flights
Midway to Las Vegas flights
George Bush Intcntl to Las Vegas flights
San Jose to Las Vegas flights
O'Hare Intl to San Francisco flights
Los Angeles to San Jose flights
Reagan-National to Las Vegas flights
Austin to Las Vegas flights
Philadelphia to Las Vegas flights
Seattle to San Francisco flights
Dallas/Fort Worth to San Francisco flights
LaGuardia to San Francisco flights
Boston to San Francisco flights
Ontario to Las Vegas flights
Oakland to Las Vegas flights

Top 3 airlines flying from Illinois to Oakland

Discover the top 3 airlines that operate flights from Illinois to Oakland. 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 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$83Average$229FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$236Average$357FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$242Average$401FlexibilityNo 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.