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Oakland

$119+ 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 1/20. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — OAK
ene. 27 — feb. 31
mar. 1/27
mar. 2/3
1 adult, Economy
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Cheap 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 diciembre 28, 2025.

This Delta deal was found by Cheapflights users on 12/27. 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.
lun. 12/297:00 amORD - OAK
2 stops11h 04mDelta
sáb. 1/105:55 amOAK - ORD
2 stops9h 59mDelta
Deal found 12/27$543
This Delta deal was found by Cheapflights users on 12/27. 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.
mar. 12/307:05 pmORD - OAK
1 stop6h 53mDelta
jue. 1/812:38 pmOAK - ORD
1 stop7h 14mDelta
Deal found 12/27$583
This Delta deal was found by Cheapflights users on 12/27. 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.
mar. 12/307:05 pmORD - OAK
1 stop6h 53mDelta
mié. 1/75:55 amOAK - ORD
2 stops9h 31mDelta
Deal found 12/27$694
This Delta deal was found by Cheapflights users on 12/26. 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.
lun. 12/294:13 pmORD - OAK
2 stops9h 45mDelta
vie. 1/25:53 amOAK - ORD
2 stops9h 54mDelta
Deal found 12/26$713
This Delta deal was found by Cheapflights users on 12/27. 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.
lun. 12/299:29 amMDW - OAK
2 stops8h 35mDelta
mar. 1/65:55 amOAK - MDW
2 stops10h 37mDelta
Deal found 12/27$713
This Delta deal was found by Cheapflights users on 12/26. 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.
mar. 12/307:05 pmORD - OAK
1 stop6h 53mDelta
mar. 1/65:55 amOAK - ORD
1 stop5h 43mDelta
Deal found 12/26$754
This Delta deal was found by Cheapflights users on 12/26. 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.
lun. 12/294:13 pmORD - OAK
2 stops9h 45mDelta
mar. 1/65:55 amOAK - ORD
1 stop5h 43mDelta
Deal found 12/26$759
This Delta deal was found by Cheapflights users on 12/26. 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.
mié. 12/311:35 pmORD - OAK
2 stops11h 12mDelta
vie. 1/25:53 amOAK - ORD
2 stops9h 54mDelta
Deal found 12/26$794
This Delta deal was found by Cheapflights users on 12/26. 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.
mar. 12/309:29 amMDW - OAK
2 stops8h 35mDelta
lun. 1/55:55 amOAK - MDW
2 stops10h 37mDelta
Deal found 12/26$794
This Alaska Airlines deal was found by Cheapflights users on 12/26. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/297:00 amORD - OAK
1 stop14h 52mAlaska Airlines
sáb. 1/108:10 amOAK - ORD
1 stop13h 40mAlaska Airlines
Deal found 12/26$803
This Delta deal was found by Cheapflights users on 12/27. 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.
mié. 12/319:50 amMDW - OAK
2 stops14h 57mDelta
vie. 1/25:53 amOAK - MDW
2 stops9h 33mDelta
Deal found 12/27$819
This Southwest deal was found by Cheapflights users on 12/26. 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.
sáb. 12/2710:50 pmMDW - OAK
Nonstop4h 40mSouthwest
mié. 1/711:10 amOAK - MDW
Nonstop4h 05mSouthwest
Deal found 12/26$828

Find flight deals from Illinois to Oakland

Keep the following information in mind while searching for Illinois to Oakland flight deals. Data was last updated diciembre 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$251
(Alaska Airlines)

One-way from

$119
(Southwest)

Popular in

December

Cheapest in

July

Average price

$449

Good round-trip deal

$627 or less

Good one-way deal

$323 or less
Provider with most accurate pricing for Chicago (CHI)-San Francisco flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-San Francisco flights.
Search Deals
From Illinois to Oakland
Search Deals
One-way flight from Illinois to Oakland
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($59 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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

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 diciembre 28, 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

mié. 2/18

3:54 pm-10:49 pm

1 stop8h 55m

Oakland

sáb. 2/21

6:15 am-4:33 pm

1 stop8h 18m

$255

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

sáb. 2/14

3:54 pm-10:49 pm

1 stop8h 55m

Oakland

mié. 2/18

6:15 am-4:33 pm

1 stop8h 18m

$263

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

jue. 1/29

11:10 am-2:05 pm

Nonstop4h 55m

Oakland

mar. 2/3

11:10 am-5:15 pm

Nonstop4h 05m

$265

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

sáb. 1/17

1:00 pm-6:30 pm

1 stop7h 30m

Oakland

dom. 1/18

5:25 am-1:30 pm

1 stop6h 05m

$270

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

mié. 2/25

3:54 pm-10:49 pm

1 stop8h 55m

Oakland

sáb. 2/28

6:15 am-4:33 pm

1 stop8h 18m

$271

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

mié. 3/11

7:20 am-11:51 am

1 stop6h 31m

Oakland

mar. 3/17

12:35 pm-9:34 pm

1 stop6h 59m

$272

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

mié. 3/4

7:15 am-11:55 am

1 stop6h 40m

Oakland

sáb. 3/7

12:40 pm-9:52 pm

1 stop7h 12m

$275

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

mié. 3/4

8:15 am-3:55 pm

1 stop9h 40m

Oakland

sáb. 3/7

3:30 pm-1:55 am

1 stop8h 25m

$275

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

vie. 1/23

8:00 am-4:23 pm

1 stop10h 23m

Oakland

mar. 1/27

11:43 am-11:50 pm

1 stop10h 07m

$275

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

dom. 1/25

6:06 pm-8:40 pm

1 stop28h 34m

Oakland

vie. 1/30

8:10 am-11:50 pm

1 stop13h 40m

$283

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/27

Showing 1-10 of 52 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 November is currently the most expensive (average of $207). 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 diciembre 28, 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 43% on airfare.

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 55m. Alaska Airlines provides one of the quickest options available for as low as $265. 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 $98 on Alaska Airlines. Other airlines that offer cheap prices include Southwest from $98 and Delta from $137 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 November is currently the most expensive (average of $207). 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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Alternative routes for Illinois to Oakland

See prices for flight routes from nearby airports that may be better suited for you.
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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 diciembre 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$83Average$223FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$236Average$420FlexibilityNo cancel feeOn-time63%

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