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Oakland

$89+ 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 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — OAK
Mar 31 — Apr 71
Tue 3/31
Tue 4/7
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 March 1, 2026.

This Alaska Airlines deal was found by Cheapflights users on 2/25. 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 5/126:00 am
ORD
-
OAK
1 stop9h 15m
Alaska Airlines
Tue 5/196:02 am
OAK
-
ORD
1 stop29h 12m
Alaska Airlines
Deal found 2/25$230
This Southwest deal was found by Cheapflights users on 2/25. 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.
Tue 5/1210:30 am
ORD
-
OAK
1 stop10h 20m
Southwest
Tue 5/1912:25 pm
OAK
-
ORD
2 stops9h 30m
Southwest
Deal found 2/25$234
This Southwest deal was found by Cheapflights users on 2/26. 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.
Fri 5/19:50 pm
MDW
-
OAK
Nonstop4h 35m
Southwest
Sun 5/35:10 pm
OAK
-
MDW
1 stop6h 45m
Southwest
Deal found 2/26$241
This CheapOair deal was found by Cheapflights users on 2/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/142:10 pm
ORD
-
OAK
1 stop11h 40m
Alaska Airlines
Tue 5/192:58 pm
OAK
-
ORD
1 stop20h 16m
Alaska Airlines
Deal found 2/26$242
This CheapOair deal was found by Cheapflights users on 2/25. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/76:00 am
ORD
-
OAK
1 stop9h 15m
Alaska Airlines
Mon 5/113:18 pm
OAK
-
ORD
1 stop19h 55m
Alaska Airlines
Deal found 2/25$244
This Southwest deal was found by Cheapflights users on 3/1. 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 4/148:50 pm
MDW
-
OAK
Nonstop4h 35m
Southwest
Tue 4/2111:55 pm
OAK
-
MDW
Nonstop4h 05m
Southwest
Deal found 3/1$245
This CheapOair deal was found by Cheapflights users on 2/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/218:20 am
ORD
-
OAK
1 stop27h 57m
Alaska Airlines
Mon 4/276:20 am
OAK
-
ORD
1 stop15h 39m
Alaska Airlines
Deal found 2/27$253
This CheapOair deal was found by Cheapflights users on 2/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/258:50 am
ORD
-
OAK
1 stop7h 48m
Alaska Airlines
Tue 4/282:09 pm
OAK
-
ORD
1 stop7h 50m
Alaska Airlines
Deal found 2/26$255
This Alaska Airlines deal was found by Cheapflights users on 2/26. 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.
Wed 4/296:00 am
ORD
-
OAK
1 stop9h 15m
Alaska Airlines
Sat 5/22:09 pm
OAK
-
ORD
1 stop7h 50m
Alaska Airlines
Deal found 2/26$259
This Southwest deal was found by Cheapflights users on 2/25. 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.
Wed 5/611:55 am
ORD
-
OAK
2 stops10h 25m
Southwest
Tue 5/121:50 pm
OAK
-
ORD
1 stop7h 05m
Southwest
Deal found 2/25$261
This CheapOair deal was found by Cheapflights users on 2/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:00 am
ORD
-
OAK
1 stop9h 15m
Alaska Airlines
Wed 4/227:19 pm
OAK
-
ORD
1 stop15h 54m
Alaska Airlines
Deal found 2/26$262
This Alaska Airlines deal was found by Cheapflights users on 2/28. 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 4/143:50 pm
STL
-
OAK
1 stop9h 53m
Alaska Airlines
Tue 4/216:40 pm
OAK
-
STL
1 stop27h 19m
Alaska Airlines
Deal found 2/28$263

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 March 1, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$224
(Alaska Airlines)

One-way from

$89
(Southwest)

Popular in

December

Cheapest in

April

Average price

$364

Good round-trip deal

$274 or less

Good one-way deal

$272 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 ($63 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
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 March 1, 2026.
Use the filters below to find and compare flights from Illinois to Oakland that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Tue 3/31

5:55 am-10:15 am

1 stop6h 20m

Oakland

Tue 4/7

9:05 pm-5:00 am

1 stop5h 55m

$285

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Fri 4/17

9:50 pm-12:25 am

Nonstop4h 35m

Oakland

Mon 4/20

11:55 pm-6:00 am

Nonstop4h 05m

$285

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Fri 4/17

4:15 pm-11:55 pm

2 stops9h 40m

Oakland

Mon 4/20

2:00 pm-11:55 pm

2 stops7h 55m

$315

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Sun 4/26

8:35 am-1:40 pm

1 stop7h 05m

Oakland

Sat 5/2

7:50 pm-5:00 am

1 stop7h 10m

$322

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Thu 5/21

9:50 pm-12:25 am

Nonstop4h 35m

Oakland

Mon 5/25

8:30 pm-4:35 am

1 stop6h 05m

$328

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Mon 6/22

6:00 pm-10:25 pm

1 stop6h 25m

Oakland

Mon 6/29

11:55 pm-6:00 am

Nonstop4h 05m

$343

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Thu 4/23

7:20 pm-12:05 am

1 stop6h 45m

Oakland

Sun 4/26

5:00 am-3:00 pm

2 stops8h 00m

$358

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Tue 3/31

5:55 am-10:15 am

1 stop6h 20m

Oakland

Sat 4/4

9:55 pm-5:40 am

1 stop5h 45m

$375

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Thu 3/12

9:30 pm-12:10 am

Nonstop4h 40m

Oakland

Wed 3/18

11:55 pm-5:55 am

Nonstop4h 00m

$377

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Tue 6/23

6:05 am-2:05 pm

2 stops10h 00m

Oakland

Tue 6/30

5:30 am-5:50 pm

2 stops10h 20m

$381

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/27

Showing 1-10 of 60 resultsSorted by cheapest first
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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 February is currently the most expensive (average of $211). 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 March 1, 2026.

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 in the evening could potentially save you up to 51% 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 6h 25m. Southwest provides one of the quickest options available for as low as $187. 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 $119 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 February is currently the most expensive (average of $211). 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 March 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$83Average$229FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$236Average$422FlexibilityNo cancel feeOn-time63%

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