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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 2/8. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — OAK
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
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 November 6, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$239
(Southwest)

One-way from

$110
(Trip.com)

Popular in

November

Cheapest in

July

Average price

$387

Good round-trip deal

$387 or less

Good one-way deal

$249 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. 12% potential increase in price ($46 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 6, 2025.

This Southwest deal was found by Cheapflights users on 11/5. 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
Sun 12/145:25 amOAK - MDW
Nonstop4h 05mSouthwest
Deal found 11/5$239
This Alaska Airlines deal was found by Cheapflights users on 11/4. 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 12/183:33 pmORD - OAK
1 stop10h 26mAlaska Airlines
Mon 1/56:10 amOAK - ORD
1 stop9h 02mAlaska Airlines
Deal found 11/4$258
This Delta deal was found by Cheapflights users on 11/4. 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 12/37:40 pmORD - OAK
1 stop6h 28mDelta
Tue 12/912:30 pmOAK - ORD
1 stop6h 51mDelta
Deal found 11/4$259
This Alaska Airlines deal was found by Cheapflights users on 11/5. 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 12/246:08 pmORD - OAK
1 stop7h 51mAlaska Airlines
Mon 1/56:10 amOAK - ORD
1 stop22h 19mAlaska Airlines
Deal found 11/5$260
This Delta deal was found by Cheapflights users on 11/4. 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 12/177:20 amORD - OAK
1 stop6h 30mDelta
Wed 1/75:55 amOAK - ORD
2 stops10h 01mDelta
Deal found 11/4$264
This Alaska Airlines deal was found by Cheapflights users on 11/5. 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 12/186:08 pmORD - OAK
1 stop7h 51mAlaska Airlines
Sun 1/48:32 pmOAK - ORD
1 stop14h 44mAlaska Airlines
Deal found 11/5$268
This Alaska Airlines deal was found by Cheapflights users on 11/5. 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 12/246:08 pmORD - OAK
1 stop7h 51mAlaska Airlines
Thu 1/16:10 amOAK - ORD
1 stop22h 19mAlaska Airlines
Deal found 11/5$270
This Alaska Airlines deal was found by Cheapflights users on 11/4. 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 12/223:33 pmORD - OAK
1 stop10h 26mAlaska Airlines
Mon 1/59:35 amOAK - ORD
2 stops24h 38mAlaska Airlines
Deal found 11/4$276
This Southwest deal was found by Cheapflights users on 11/6. 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.
Fri 12/124:25 pmORD - OAK
1 stop8h 35mSouthwest
Wed 12/175:25 amOAK - ORD
1 stop6h 05mSouthwest
Deal found 11/6$279
This Southwest deal was found by Cheapflights users on 11/5. 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.
Fri 12/54:05 pmMDW - OAK
Nonstop4h 35mSouthwest
Fri 12/125:25 amOAK - MDW
Nonstop4h 05mSouthwest
Deal found 11/5$299
This Southwest deal was found by Cheapflights users on 11/4. 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 12/115:15 amMDW - OAK
1 stop6h 55mSouthwest
Thu 12/1112:45 pmOAK - MDW
1 stop8h 10mSouthwest
Deal found 11/4$331
This Southwest deal was found by Cheapflights users on 11/5. 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.
Fri 12/196:05 amMDW - OAK
1 stop7h 25mSouthwest
Mon 1/54:25 pmOAK - MDW
1 stop5h 55mSouthwest
Deal found 11/5$349

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 November 6, 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

MDW - OAK

MDWOAK

Chicago Midway

Sat 12/6

2:05 pm-4:45 pm

Nonstop4h 40m

Oakland

Sun 12/14

5:25 am-11:30 am

Nonstop4h 05m

$239

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Thu 12/11

4:05 pm-6:40 pm

Nonstop4h 35m

Oakland

Mon 1/5

4:25 pm-12:20 am

1 stop5h 55m

$249

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Thu 1/22

2:06 pm-7:23 pm

1 stop7h 17m

Oakland

Mon 1/26

5:17 pm-11:50 pm

1 stop28h 33m

$260

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Tue 3/10

7:45 am-5:43 pm

1 stop11h 58m

Oakland

Wed 3/11

6:35 pm-5:04 am

1 stop8h 29m

$262

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Thu 12/18

1:09 pm-11:59 pm

1 stop12h 50m

Oakland

Mon 1/5

6:10 am-12:13 pm

1 stop28h 03m

$272

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Thu 1/22

3:35 pm-4:23 pm

1 stop26h 48m

Oakland

Thu 1/29

8:10 am-11:50 pm

1 stop13h 40m

$283

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Sat 2/21

8:05 am-2:00 pm

1 stop7h 55m

Oakland

Sat 2/28

8:00 am-6:10 pm

1 stop8h 10m

$288

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Thu 1/15

8:05 am-2:55 pm

1 stop8h 50m

Oakland

Sun 1/25

6:30 am-12:35 pm

Nonstop4h 05m

$291

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Wed 12/24

6:08 pm-2:07 pm

1 stop21h 59m

Oakland

Wed 12/31

8:32 pm-1:16 pm

1 stop14h 44m

$292

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Mon 1/5

3:00 pm-9:20 pm

1 stop8h 20m

Oakland

Tue 1/6

5:25 am-2:45 pm

1 stop7h 20m

$301

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/5

Showing 1-10 of 54 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 November 6, 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 4h 40m. Southwest provides one of the quickest options available for as low as $239. Illinois and Oakland, California are separated by a distance of 1839 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 $129 on Alaska Airlines. Other airlines that offer cheap prices include Southwest from $130 and Delta from $130 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 November 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$83Average$234FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$245Average$441FlexibilityNo cancel feeOn-time63%

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