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$110+ 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 1/24. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — OAK
Nov 26 — Dec 31
Wed 11/26
Wed 12/3
1 adult, Economy
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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 October 27, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$261
(Delta)

One-way from

$110
(Kissandfly.com)

Popular in

December

Cheapest in

July

Average price

$321

Good round-trip deal

$336 or less

Good one-way deal

$306 or less
Provider with most accurate pricing for Chicago (CHI)-San Francisco flight deals.
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From Illinois to Oakland
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One-way flight from Illinois to Oakland
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Highest demand for flights based on searches. 10% potential increase in price ($37 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Illinois to Oakland.
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Price to beat on a one-way flight from Illinois to Oakland.
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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 October 27, 2025.

This Delta deal was found by Cheapflights users on 10/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/107:40 pmORD - OAK
1 stop6h 28mDelta
Wed 1/75:55 amOAK - ORD
1 stop5h 43mDelta
Deal found 10/27$261
This Delta deal was found by Cheapflights users on 10/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/137:20 amORD - OAK
1 stop6h 30mDelta
Thu 1/85:55 amOAK - ORD
2 stops9h 26mDelta
Deal found 10/27$266
This Delta deal was found by Cheapflights users on 10/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/51:14 pmMDW - OAK
2 stops12h 54mDelta
Sun 12/75:55 amOAK - MDW
2 stops10h 05mDelta
Deal found 10/26$271
This Alaska Airlines deal was found by Cheapflights users on 10/24. 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.
Fri 11/145:53 pmORD - OAK
1 stop8h 06mAlaska Airlines
Sun 11/166:30 amOAK - ORD
1 stop21h 52mAlaska Airlines
Deal found 10/24$283
This Southwest deal was found by Cheapflights users on 10/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/226:15 pmORD - OAK
1 stop7h 00mSouthwest
Thu 11/275:15 amOAK - ORD
1 stop6h 50mSouthwest
Deal found 10/25$286
This Delta deal was found by Cheapflights users on 10/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/127:40 pmORD - OAK
1 stop6h 28mDelta
Sun 12/1412:30 pmOAK - ORD
1 stop6h 51mDelta
Deal found 10/26$290
This Alaska Airlines deal was found by Cheapflights users on 10/25. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/95:51 pmORD - OAK
1 stop8h 08mAlaska Airlines
Tue 12/166:40 amOAK - ORD
1 stop13h 50mAlaska Airlines
Deal found 10/25$292
This Cheapflightsfares deal was found by Cheapflights users on 10/26. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/55:51 pmORD - OAK
1 stop8h 08mAlaska Airlines
Sat 12/132:31 pmOAK - ORD
1 stop7h 28mAlaska Airlines
Deal found 10/26$299
This Delta deal was found by Cheapflights users on 10/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/237:40 pmORD - OAK
1 stop6h 23mDelta
Thu 11/275:55 amOAK - ORD
1 stop5h 49mDelta
Deal found 10/25$300
This Delta deal was found by Cheapflights users on 10/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/131:14 pmMDW - OAK
2 stops10h 46mDelta
Mon 12/155:55 amOAK - MDW
2 stops10h 23mDelta
Deal found 10/26$300
This Alaska Airlines deal was found by Cheapflights users on 10/27. 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 12/103:35 pmORD - OAK
1 stop21h 06mAlaska Airlines
Mon 1/53:01 pmOAK - ORD
1 stop24h 11mAlaska Airlines
Deal found 10/27$302
This Southwest deal was found by Cheapflights users on 10/26. 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.
Sat 12/62:05 pmMDW - OAK
Nonstop4h 40mSouthwest
Mon 12/87:55 amOAK - MDW
1 stop6h 15mSouthwest
Deal found 10/26$308

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 October 27, 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

Wed 12/10

7:20 am-11:50 am

1 stop6h 30m

Oakland

Thu 1/8

12:38 pm-9:52 pm

1 stop7h 14m

$261

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Mon 12/15

7:40 pm-12:08 am

1 stop6h 28m

Oakland

Thu 1/8

12:38 pm-9:52 pm

1 stop7h 14m

$261

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Fri 12/5

7:40 pm-12:08 am

1 stop6h 28m

Oakland

Sun 12/7

5:55 am-6:27 pm

2 stops10h 32m

$266

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Fri 12/5

1:14 pm-12:08 am

2 stops12h 54m

Oakland

Sun 12/7

5:55 am-6:00 pm

2 stops10h 05m

$271

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Wed 1/14

6:43 pm-10:53 pm

1 stop6h 10m

Oakland

Tue 1/20

4:54 pm-11:53 pm

2 stops28h 59m

$277

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Fri 1/16

6:06 pm-4:28 pm

1 stop24h 22m

Oakland

Tue 1/20

11:43 am-11:55 pm

1 stop10h 12m

$282

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Tue 2/17

6:50 pm-5:43 pm

1 stop24h 53m

Oakland

Mon 2/23

6:30 am-5:04 am

1 stop20h 34m

$283

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Fri 11/14

5:53 pm-11:59 pm

1 stop8h 06m

Oakland

Sat 11/15

2:49 pm-12:24 am

1 stop7h 35m

$283

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Sat 11/22

6:15 pm-11:15 pm

1 stop7h 00m

Oakland

Thu 11/27

5:15 am-2:05 pm

1 stop6h 50m

$286

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Thu 1/15

8:00 am-7:23 pm

2 stops13h 23m

Oakland

Tue 1/20

11:43 am-11:55 pm

1 stop10h 12m

$288

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

Showing 1-10 of 60 results
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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, October is the cheapest month in which you can book a flight from Illinois to Oakland, California (average of $80). Flying from Illinois to Oakland, California in June is currently the most expensive (average of $198). 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 October 27, 2025.

One of the essential ways to save on airfare from Illinois to Oakland, California is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight at noon could potentially save you up to 26% on airfare.

What is the cheapest day to fly from Illinois to Oakland, California?

Use this chart to determine the cheapest time to fly round-trip from Illinois to Oakland. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Illinois to Oakland, California flight should consider departing on Sunday afternoons when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 6h 30m. Delta provides one of the quickest options available for as low as $261. 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 $117 on Southwest. Other airlines that offer cheap prices include Delta from $131 and Alaska Airlines from $170 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, October is the cheapest month in which you can book a flight from Illinois to Oakland, California (average of $80). Flying from Illinois to Oakland, California in June is currently the most expensive (average of $198). 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

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Top 2 airlines flying from Illinois to Oakland

Discover the top 2 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 October 27, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$83Average$234FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$245Average$440FlexibilityNo cancel feeOn-time63%

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