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Oakland

$72+ 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 9/12. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — OAK
Jul 6 — Jul 131
Sun 7/6
Sun 7/13
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 July 1, 2025.

Round-trip from

$169
(Booking.com)

One-way from

$72
(FlightHub)

Popular in

December

Cheapest in

September

Average price

$293

Good round-trip deal

$643 or less

Good one-way deal

$313 or less
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. 8% potential increase in price ($28 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 1, 2025.

This Booking.com deal was found by Cheapflights users on 6/29. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/173:21 pmORD - OAK
1 stop6h 53mSpirit Airlines
Sun 10/199:09 pmOAK - ORD
1 stop15h 07mSpirit Airlines
Deal found 6/29$173
This Southwest deal was found by Cheapflights users on 6/30. 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.
Sat 8/233:25 pmMDW - OAK
Nonstop4h 30mSouthwest
Sun 8/318:15 amOAK - MDW
Nonstop4h 05mSouthwest
Deal found 6/30$188
This Southwest deal was found by Cheapflights users on 6/30. 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.
Tue 7/225:25 pmORD - OAK
1 stop6h 50mSouthwest
Fri 7/252:00 pmOAK - ORD
1 stop7h 05mSouthwest
Deal found 6/30$227
This Delta deal was found by Cheapflights users on 6/30. 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.
Tue 7/229:24 amMDW - OAK
2 stops8h 50mDelta
Fri 7/254:55 pmOAK - MDW
2 stops13h 49mDelta
Deal found 6/30$298
This Delta deal was found by Cheapflights users on 7/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/127:35 amSTL - OAK
1 stop6h 20mDelta
Sat 8/164:58 pmOAK - STL
1 stop5h 40mDelta
Deal found 7/1$353
This Alaska Airlines deal was found by Cheapflights users on 6/29. 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.
Mon 9/156:30 pmSTL - OAK
2 stops26h 48mAlaska Airlines
Thu 9/186:15 amOAK - STL
1 stop9h 19mAlaska Airlines
Deal found 6/29$362
This Mytrip deal was found by Cheapflights users on 6/30. 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.
Mon 7/2810:47 amSTL - OAK
2 stops23h 41mSpirit Airlines
Mon 8/49:23 amOAK - STL
2 stops29h 08mSpirit Airlines
Deal found 6/30$363
This Southwest deal was found by Cheapflights users on 6/30. 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 8/61:20 pmSTL - OAK
1 stop5h 25mSouthwest
Sun 8/103:55 pmOAK - STL
1 stop7h 20mSouthwest
Deal found 6/30$371
This Mytrip deal was found by Cheapflights users on 6/30. 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.
Mon 7/289:20 amSTL - OAK
3 stops40h 13mMultiple Airlines
Mon 8/49:23 amOAK - STL
2 stops29h 08mMultiple Airlines
Deal found 6/30$395
This Delta deal was found by Cheapflights users on 6/29. 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.
Sat 8/236:05 amBMI - OAK
2 stops12h 11mDelta
Tue 8/2612:35 pmOAK - BMI
2 stops31h 41mDelta
Deal found 6/29$553
This Mytrip deal was found by Cheapflights users on 7/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/138:44 pmPIA - OAK
2 stops25h 41mMultiple Airlines
Tue 7/156:00 amOAK - PIA
3 stops23h 59mMultiple Airlines
Deal found 7/1$639
This Delta deal was found by Cheapflights users on 7/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/45:57 amMLI - OAK
2 stops18h 51mDelta
Tue 10/71:15 pmOAK - MLI
2 stops25h 07mDelta
Deal found 7/1$643

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 July 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

Mon 8/18

5:35 pm-11:27 pm

1 stop7h 52m

Oakland

Wed 8/20

6:00 am-5:15 pm

1 stop9h 15m

$169

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Sat 8/23

3:25 pm-5:55 pm

Nonstop4h 30m

Oakland

Sun 8/31

8:15 am-2:20 pm

Nonstop4h 05m

$188

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Sat 8/23

6:15 am-1:40 pm

2 stops9h 25m

Oakland

Sun 8/31

7:40 am-5:55 pm

2 stops8h 15m

$218

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Fri 8/15

5:55 pm-12:01 am

1 stop8h 06m

Oakland

Fri 8/22

7:07 pm-5:00 am

1 stop7h 53m

$221

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Tue 7/22

9:24 am-4:14 pm

2 stops8h 50m

Oakland

Fri 7/25

4:55 pm-8:44 am

2 stops13h 49m

$298

St. LouisOakland

STL - OAK

STLOAK

Lambert-St Louis

Tue 8/12

7:35 am-11:55 am

1 stop6h 20m

Oakland

Sat 8/16

4:58 pm-12:38 am

1 stop5h 40m

$353

St. LouisOakland

STL - OAK

STLOAK

Lambert-St Louis

Mon 9/15

6:30 pm-7:18 pm

2 stops26h 48m

Oakland

Thu 9/18

6:15 am-5:34 pm

1 stop9h 19m

$362

St. LouisOakland

STL - OAK

STLOAK

Lambert-St Louis

Mon 7/28

10:47 am-8:28 am

2 stops23h 41m

Oakland

Mon 8/4

9:23 am-4:31 pm

2 stops29h 08m

$363

St. LouisOakland

STL - OAK

STLOAK

Lambert-St Louis

Wed 8/6

1:20 pm-4:45 pm

1 stop5h 25m

Oakland

Sun 8/10

3:55 pm-1:15 am

1 stop7h 20m

$371

St. LouisOakland

STL - OAK

STLOAK

Lambert-St Louis

Mon 7/28

9:20 am-11:33 pm

3 stops40h 13m

Oakland

Mon 8/4

9:23 am-4:31 pm

2 stops29h 08m

$395

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

Showing 1-10 of 28 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 July 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.

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 July 1, 2025.
Read through reviews of airlines operating flights from Illinois to Oakland, such as Alaska Airlines, Southwest, and Delta. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Entertainment

7.1

Food

7.1

Crew

8.5

Overall

8.0

Comfort

7.8

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
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Entertainment

7.1

Food

7.1

Crew

8.5

Overall

8.0

Comfort

7.8

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
4,273 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Entertainment

7.1

Food

7.1

Crew

8.5

Overall

8.0

Comfort

7.8

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
7,973 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Entertainment

7.1

Food

7.1

Crew

8.5

Overall

8.0

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.8
Good
2,539 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Entertainment

7.1

Food

7.1

Crew

8.5

Overall

8.0

Comfort

7.8

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
340 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Entertainment

7.1

Food

7.1

Crew

8.5

Overall

8.0

Comfort

7.8

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 $72 on Spirit Airlines. Other airlines that offer cheap prices include Southwest from $90 and Hawaiian 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 3 airlines flying from Illinois to Oakland

Discover the top 3 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 July 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$127Average$219FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$238Average$362FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$246Average$382FlexibilityNo cancel feeOn-time63%

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