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Oakland

$75+ 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 5/20. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — OAK
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
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 April 17, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$156
(eDestinos)

One-way from

$75
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$288

Good round-trip deal

$352 or less

Good one-way deal

$166 or less
Provider with most accurate pricing for Chicago (CHI)-San Francisco flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-San Francisco flights.
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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. 7% potential increase in price ($24 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 April 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 April 17, 2025.

This eDestinos deal was found by Cheapflights users on 4/16. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/79:02 pmORD - OAK
2 stops14h 39mSpirit Airlines
Tue 5/139:09 pmOAK - ORD
1 stop11h 46mSpirit Airlines
Deal found 4/16$156
This Southwest deal was found by Cheapflights users on 4/17. 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.
Fri 5/309:10 pmMDW - OAK
Nonstop4h 35mSouthwest
Sun 6/15:55 amOAK - MDW
Nonstop4h 10mSouthwest
Deal found 4/17$198
This Southwest deal was found by Cheapflights users on 4/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/296:55 pmORD - OAK
1 stop6h 25mSouthwest
Sat 5/315:20 amOAK - ORD
1 stop7h 40mSouthwest
Deal found 4/15$199
This Alaska Airlines deal was found by Cheapflights users on 4/16. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/316:00 amORD - OAK
1 stop9h 36mAlaska Airlines
Sat 6/72:31 pmOAK - ORD
1 stop7h 28mAlaska Airlines
Deal found 4/16$242
This Delta deal was found by Cheapflights users on 4/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/107:20 pmORD - OAK
1 stop6h 37mDelta
Wed 6/1812:30 pmOAK - ORD
1 stop7h 39mDelta
Deal found 4/16$257
This Delta deal was found by Cheapflights users on 4/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/79:20 amMDW - OAK
2 stops8h 55mDelta
Tue 5/136:00 amOAK - MDW
2 stops9h 45mDelta
Deal found 4/16$267
This Hawaiian Airlines deal was found by Cheapflights users on 4/16. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/63:44 pmORD - OAK
1 stop7h 32mHawaiian Airlines
Tue 5/202:31 pmOAK - ORD
1 stop7h 28mHawaiian Airlines
Deal found 4/16$276
This Mytrip deal was found by Cheapflights users on 4/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/236:12 pmORD - OAK
2 stops28h 02mMultiple Airlines
Mon 5/269:09 pmOAK - ORD
1 stop6h 16mMultiple Airlines
Deal found 4/17$320
This Delta deal was found by Cheapflights users on 4/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/147:30 amSTL - OAK
1 stop6h 26mDelta
Sat 5/1712:39 pmOAK - STL
1 stop6h 53mDelta
Deal found 4/17$327
This Alaska Airlines deal was found by Cheapflights users on 4/16. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/63:08 pmSTL - OAK
1 stop10h 36mAlaska Airlines
Sun 5/116:00 amOAK - STL
1 stop15h 59mAlaska Airlines
Deal found 4/16$364
This Mytrip deal was found by Cheapflights users on 4/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/1110:10 amSTL - OAK
3 stops25h 31mSpirit Airlines
Fri 5/169:09 pmOAK - STL
2 stops34h 06mSpirit Airlines
Deal found 4/17$411
This Mytrip deal was found by Cheapflights users on 4/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1412:15 pmSTL - OAK
3 stops33h 59mMultiple Airlines
Sat 5/175:45 amOAK - STL
2 stops25h 30mMultiple Airlines
Deal found 4/17$532

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 April 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

Wed 5/7

9:02 pm-9:41 am

2 stops14h 39m

Oakland

Tue 5/13

9:09 pm-10:55 am

1 stop11h 46m

$156

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Fri 5/30

9:10 pm-11:45 pm

Nonstop4h 35m

Oakland

Sun 6/1

5:55 am-12:05 pm

Nonstop4h 10m

$198

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Thu 5/29

6:55 pm-11:20 pm

1 stop6h 25m

Oakland

Sat 5/31

5:20 am-3:00 pm

1 stop7h 40m

$199

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Sat 5/31

6:00 am-1:36 pm

1 stop9h 36m

Oakland

Sat 6/7

2:31 pm-11:59 pm

1 stop7h 28m

$242

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Tue 6/10

7:20 pm-11:57 pm

1 stop6h 37m

Oakland

Wed 6/18

12:30 pm-10:09 pm

1 stop7h 39m

$257

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Wed 5/7

9:20 am-4:15 pm

2 stops8h 55m

Oakland

Tue 5/13

6:00 am-5:45 pm

2 stops9h 45m

$267

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Tue 5/6

3:44 pm-9:16 pm

1 stop7h 32m

Oakland

Tue 5/20

2:31 pm-11:59 pm

1 stop7h 28m

$276

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Fri 5/23

6:12 pm-8:14 pm

2 stops28h 02m

Oakland

Mon 5/26

9:09 pm-5:25 am

1 stop6h 16m

$320

St. LouisOakland

STL - OAK

STLOAK

Lambert-St Louis

Wed 5/14

7:30 am-11:56 am

1 stop6h 26m

Oakland

Sat 5/17

12:39 pm-9:32 pm

1 stop6h 53m

$327

St. LouisOakland

STL - OAK

STLOAK

Lambert-St Louis

Tue 5/6

3:08 pm-11:44 pm

1 stop10h 36m

Oakland

Sun 5/11

6:00 am-11:59 pm

1 stop15h 59m

$364

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/16

Showing 1-10 of 31 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, 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 April 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.

Rainfall in Oakland by month

Plan your trip to Oakland by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Oakland, California ranges from 0.0 - 4.8 inches per month. January is typically the wettest month, when rainfall can reach 4.8 in. July is typically the driest time to visit Oakland, California when rainfall is around 0.0 in.

Temperature in Oakland by month

Plan your trip to Oakland by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Oakland, California, use this chart to help with planning. For those seeking warmer temperatures, August is the ideal time of year to visit, when temperatures reach an average of 66.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 51.8 F).

Reviews of airlines servicing Oakland

Get insights into the airlines that provide service to Oakland. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Oakland. Reviews last updated April 17, 2025.
See what other customers who have flown with Alaska Airlines, Southwest and Delta from Illinois to Oakland have to say. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,882 reviews

Boarding

8.2

Crew

8.5

Food

7.1

Entertainment

7.1

Comfort

7.9

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,882 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Boarding

8.2

Crew

8.5

Food

7.1

Entertainment

7.1

Comfort

7.9

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Southwest
8.0
Very good
4,280 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Boarding

8.2

Crew

8.5

Food

7.1

Entertainment

7.1

Comfort

7.9

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,917 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Boarding

8.2

Crew

8.5

Food

7.1

Entertainment

7.1

Comfort

7.9

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Hawaiian Airlines
7.9
Good
2,382 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Boarding

8.2

Crew

8.5

Food

7.1

Entertainment

7.1

Comfort

7.9

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Sun Country Air
6.9
Okay
349 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Boarding

8.2

Crew

8.5

Food

7.1

Entertainment

7.1

Comfort

7.9

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

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.

  • 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 $75 on Spirit Airlines. Other airlines that offer cheap prices include Southwest from $90 and Alaska Airlines from $108 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

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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 4 airlines flying from Illinois to Oakland

Discover the top 4 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 April 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$129Average$242FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$238Average$362FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$247Average$396FlexibilityNo cancel feeOn-time63%
DeltaCheapest$256Average$416FlexibilityNo cancel feeOn-timeN/A

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