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Oakland

$66+ 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 6/3. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — OAK
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$136
(Cheapflightsfares)

One-way from

$66
(FlightHub)

Popular in

December

Cheapest in

September

Average price

$297

Good round-trip deal

$287 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 May 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 May 1, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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.
Tue 6/311:50 amORD - OAK
1 stop10h 24mSpirit Airlines
Mon 6/99:09 pmOAK - ORD
1 stop11h 46mSpirit Airlines
Deal found 4/29$136
This Alaska Airlines deal was found by Cheapflights users on 4/29. 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 5/288:00 amORD - OAK
1 stop7h 36mAlaska Airlines
Sat 5/3112:48 pmOAK - ORD
1 stop9h 11mAlaska Airlines
Deal found 4/29$206
This Orbitz deal was found by Cheapflights users on 4/29. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/296:00 amORD - OAK
1 stop8h 08mMultiple Airlines
Thu 6/59:09 pmOAK - ORD
1 stop6h 16mMultiple Airlines
Deal found 4/29$234
This Southwest deal was found by Cheapflights users on 4/29. 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 6/48:35 amMDW - OAK
1 stop6h 25mSouthwest
Tue 6/104:25 pmOAK - MDW
1 stop6h 25mSouthwest
Deal found 4/29$247
This Delta deal was found by Cheapflights users on 4/29. 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.
Thu 6/57:15 pmORD - OAK
1 stop6h 34mDelta
Wed 6/1112:30 pmOAK - ORD
1 stop7h 39mDelta
Deal found 4/29$257
This Delta deal was found by Cheapflights users on 4/29. 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 5/301:55 pmMDW - OAK
2 stops11h 54mDelta
Mon 6/26:00 amOAK - MDW
2 stops9h 45mDelta
Deal found 4/29$267
This Delta deal was found by Cheapflights users on 4/30. 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 5/237:19 pmSTL - OAK
1 stop6h 30mDelta
Wed 5/286:00 amOAK - STL
1 stop5h 34mDelta
Deal found 4/30$337
This Mytrip deal was found by Cheapflights users on 4/30. 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 5/288:49 amMLI - OAK
3 stops39h 36mMultiple Airlines
Wed 6/411:51 amOAK - MLI
1 stop21h 55mMultiple Airlines
Deal found 4/30$356
This Hawaiian Airlines deal was found by Cheapflights users on 4/30. 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.
Wed 10/227:00 amSTL - OAK
1 stop8h 35mHawaiian Airlines
Mon 10/272:35 pmOAK - STL
1 stop7h 21mHawaiian Airlines
Deal found 4/30$360
This Southwest deal was found by Cheapflights users on 4/30. 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 6/112:00 pmSTL - OAK
1 stop7h 30mSouthwest
Thu 6/192:25 pmOAK - STL
1 stop8h 15mSouthwest
Deal found 4/30$362
This Alaska Airlines deal was found by Cheapflights users on 4/30. 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 11/67:00 amSTL - OAK
1 stop8h 35mAlaska Airlines
Sun 11/910:10 amOAK - STL
1 stop11h 46mAlaska Airlines
Deal found 4/30$405
This Mytrip deal was found by Cheapflights users on 4/30. 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.
Thu 5/89:50 amSTL - OAK
3 stops27h 06mMultiple Airlines
Sat 5/105:45 amOAK - STL
2 stops25h 30mMultiple Airlines
Deal found 4/30$456

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 May 1, 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

Tue 6/3

11:50 am-8:14 pm

1 stop10h 24m

Oakland

Mon 6/9

9:09 pm-10:55 am

1 stop11h 46m

$136

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Wed 5/28

8:00 am-1:36 pm

1 stop7h 36m

Oakland

Sat 5/31

12:48 pm-11:59 pm

1 stop9h 11m

$206

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Thu 5/29

6:00 am-12:08 pm

1 stop8h 08m

Oakland

Thu 6/5

9:09 pm-5:25 am

1 stop6h 16m

$234

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Wed 6/4

8:35 am-1:00 pm

1 stop6h 25m

Oakland

Tue 6/10

4:25 pm-12:50 am

1 stop6h 25m

$247

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Thu 6/5

7:15 pm-11:49 pm

1 stop6h 34m

Oakland

Tue 6/10

12:30 pm-10:09 pm

1 stop7h 39m

$257

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Fri 5/30

1:55 pm-11:49 pm

2 stops11h 54m

Oakland

Mon 6/2

6:00 am-5:45 pm

2 stops9h 45m

$267

St. LouisOakland

STL - OAK

STLOAK

Lambert-St Louis

Fri 5/23

7:19 pm-11:49 pm

1 stop6h 30m

Oakland

Wed 5/28

6:00 am-1:34 pm

1 stop5h 34m

$337

MolineOakland

MLI - OAK

MLIOAK

Moline Quad-City

Wed 5/28

8:49 am-10:25 pm

3 stops39h 36m

Oakland

Wed 6/4

11:51 am-11:46 am

1 stop21h 55m

$356

St. LouisOakland

STL - OAK

STLOAK

Lambert-St Louis

Wed 6/11

2:00 pm-7:30 pm

1 stop7h 30m

Oakland

Thu 6/19

2:25 pm-12:40 am

1 stop8h 15m

$362

St. LouisOakland

STL - OAK

STLOAK

Lambert-St Louis

Wed 5/28

6:52 am-7:14 pm

2 stops14h 22m

Oakland

Wed 6/4

6:52 pm-9:18 am

2 stops12h 26m

$425

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 26 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 May 1, 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 May 1, 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
9,972 reviews

Food

7.1

Entertainment

7.1

Comfort

7.9

Crew

8.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
9,972 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Food

7.1

Entertainment

7.1

Comfort

7.9

Crew

8.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,294 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Food

7.1

Entertainment

7.1

Comfort

7.9

Crew

8.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,934 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Food

7.1

Entertainment

7.1

Comfort

7.9

Crew

8.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.9
Good
2,409 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Food

7.1

Entertainment

7.1

Comfort

7.9

Crew

8.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Sun Country Air
6.9
Okay
346 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Food

7.1

Entertainment

7.1

Comfort

7.9

Crew

8.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 $66 on Spirit Airlines. Other airlines that offer cheap prices include Southwest from $100 and Hawaiian Airlines from $103 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$129Average$242FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$238Average$362FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$247Average$390FlexibilityNo cancel feeOn-time63%
DeltaCheapest$256Average$416FlexibilityNo cancel feeOn-timeN/A

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