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$52+ 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 4/16. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — OAK
Feb 27 — Mar 61
Thu 2/27
Thu 3/6
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 February 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$116
(Cheapflightsfares)

One-way from

$52
(Booking.com)

Popular in

March

Cheapest in

April

Average price

$297

Good round-trip deal

$383 or less

Good one-way deal

$198 or less
Provider with most accurate pricing for Chicago (CHI)-San Francisco flight deals.
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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. 0% potential increase in price ($2 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 February 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 February 22, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 2/21. 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.
Sat 4/58:09 amORD - OAK
1 stop11h 46mSpirit Airlines
Mon 4/146:40 pmOAK - ORD
1 stop9h 53mSpirit Airlines
Deal found 2/21$116
This Kiwi.com deal was found by Cheapflights users on 2/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/85:53 pmORD - OAK
1 stop7h 50mMultiple Airlines
Tue 4/156:40 pmOAK - ORD
1 stop9h 53mMultiple Airlines
Deal found 2/22$196
This Alaska Airlines deal was found by Cheapflights users on 2/21. 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 4/77:16 pmORD - OAK
1 stop30h 27mAlaska Airlines
Mon 4/146:43 amOAK - ORD
1 stop21h 16mAlaska Airlines
Deal found 2/21$216
This Southwest deal was found by Cheapflights users on 2/21. 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 4/259:10 pmMDW - OAK
Nonstop4h 35mSouthwest
Tue 4/295:50 amOAK - MDW
Nonstop4h 10mSouthwest
Deal found 2/21$227
This Hawaiian Airlines deal was found by Cheapflights users on 2/21. 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.
Fri 9/265:10 pmORD - OAK
1 stop8h 28mHawaiian Airlines
Thu 10/26:45 pmOAK - ORD
1 stop8h 19mHawaiian Airlines
Deal found 2/21$276
This Delta deal was found by Cheapflights users on 2/21. 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 3/87:20 amORD - OAK
1 stop7h 10mDelta
Sat 3/156:00 amOAK - ORD
1 stop5h 52mDelta
Deal found 2/21$297
This Delta deal was found by Cheapflights users on 2/22. 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 4/236:25 pmSTL - OAK
1 stop7h 18mDelta
Wed 4/306:00 amOAK - STL
1 stop5h 28mDelta
Deal found 2/22$317
This Delta deal was found by Cheapflights users on 2/20. 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 10/23:40 pmMDW - OAK
1 stop7h 52mDelta
Mon 10/610:45 pmOAK - MDW
1 stop8h 33mDelta
Deal found 2/20$343
This Southwest deal was found by Cheapflights users on 2/21. 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 5/2212:50 pmSTL - OAK
1 stop8h 25mSouthwest
Mon 5/265:05 pmOAK - STL
1 stop5h 45mSouthwest
Deal found 2/21$391
This Mytrip deal was found by Cheapflights users on 2/22. 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 4/2312:15 pmSTL - OAK
3 stops31h 20mMultiple Airlines
Wed 4/3011:32 amOAK - STL
2 stops27h 44mMultiple Airlines
Deal found 2/22$451
This Mytrip deal was found by Cheapflights users on 2/21. 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.
Sat 3/811:54 amPIA - OAK
2 stops20h 22mMultiple Airlines
Wed 3/1210:30 amOAK - PIA
2 stops29h 05mMultiple Airlines
Deal found 2/21$467
This Alaska Airlines deal was found by Cheapflights users on 2/21. 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.
Sun 4/66:44 amSTL - OAK
1 stop18h 59mAlaska Airlines
Wed 4/910:50 amOAK - STL
2 stops11h 09mAlaska Airlines
Deal found 2/21$486

Find flights from Illinois to Oakland within your budget

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 February 22, 2025.

Fly from

Illinois

Fly to

Oakland

Route

Depart

Return

Price

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Sat 4/5

8:09 am-5:55 pm

1 stop11h 46m

Oakland

Mon 4/14

6:40 pm-6:33 am

1 stop9h 53m

$116

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Tue 4/8

5:53 pm-11:43 pm

1 stop7h 50m

Oakland

Tue 4/15

6:40 pm-6:33 am

1 stop9h 53m

$196

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Mon 4/7

7:16 pm-11:43 pm

1 stop30h 27m

Oakland

Mon 4/14

6:43 am-5:59 am

1 stop21h 16m

$216

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Fri 4/25

9:10 pm-11:45 pm

Nonstop4h 35m

Oakland

Tue 4/29

5:50 am-12:00 pm

Nonstop4h 10m

$227

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Sat 3/8

7:20 am-12:30 pm

1 stop7h 10m

Oakland

Sat 3/15

6:00 am-1:52 pm

1 stop5h 52m

$297

St. LouisOakland

STL - OAK

STLOAK

Lambert-St Louis

Wed 4/23

6:25 pm-11:43 pm

1 stop7h 18m

Oakland

Wed 4/30

6:00 am-1:28 pm

1 stop5h 28m

$317

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Tue 4/8

2:57 pm-11:46 pm

2 stops10h 49m

Oakland

Tue 4/15

6:00 am-6:20 pm

2 stops10h 20m

$352

St. LouisOakland

STL - OAK

STLOAK

Lambert-St Louis

Thu 5/22

12:50 pm-7:15 pm

1 stop8h 25m

Oakland

Mon 5/26

5:05 pm-12:50 am

1 stop5h 45m

$391

St. LouisOakland

STL - OAK

STLOAK

Lambert-St Louis

Wed 4/23

12:15 pm-5:35 pm

3 stops31h 20m

Oakland

Wed 4/30

11:32 am-5:16 pm

2 stops27h 44m

$451

PeoriaOakland

PIA - OAK

PIAOAK

Greater Peoria

Sat 3/8

11:54 am-6:16 am

2 stops20h 22m

Oakland

Wed 3/12

10:30 am-5:35 pm

2 stops29h 05m

$467

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/21

Showing 1-10 of 25 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.

Travel insights for flights from Illinois to Oakland

Get recent, data-driven insights about flights from Illinois to Oakland including ideal travel times, pricing trends, and more.

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 February 22, 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 February 22, 2025.
See what other customers who have flown with Southwest, Alaska Airlines 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.
Southwest
8.1
Very good
4,395 reviews

Overall

8.1

Entertainment

7.6

Crew

8.7

Comfort

8.1

Food

7.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Bhoopal,Nov 2024

STL - BOS

Flight was delayed by one hour and 40 minutes. Also baggage was delivered late at Boston. This delay made me miss my connection from Boston to Hyderabad

Southwest
8.1
Very good
4,395 reviews
Southwest
8.1
Very good
4,395 reviews

Overall

8.1

Entertainment

7.6

Crew

8.7

Comfort

8.1

Food

7.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Bhoopal,Nov 2024

STL - BOS

Flight was delayed by one hour and 40 minutes. Also baggage was delivered late at Boston. This delay made me miss my connection from Boston to Hyderabad

Alaska Airlines
8.0
Very good
9,700 reviews
Southwest
8.1
Very good
4,395 reviews

Overall

8.1

Entertainment

7.6

Crew

8.7

Comfort

8.1

Food

7.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Bhoopal,Nov 2024

STL - BOS

Flight was delayed by one hour and 40 minutes. Also baggage was delivered late at Boston. This delay made me miss my connection from Boston to Hyderabad

Delta
8.0
Very good
8,203 reviews
Southwest
8.1
Very good
4,395 reviews

Overall

8.1

Entertainment

7.6

Crew

8.7

Comfort

8.1

Food

7.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Bhoopal,Nov 2024

STL - BOS

Flight was delayed by one hour and 40 minutes. Also baggage was delivered late at Boston. This delay made me miss my connection from Boston to Hyderabad

Spirit Airlines
6.3
Okay
8,012 reviews
Southwest
8.1
Very good
4,395 reviews

Overall

8.1

Entertainment

7.6

Crew

8.7

Comfort

8.1

Food

7.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Bhoopal,Nov 2024

STL - BOS

Flight was delayed by one hour and 40 minutes. Also baggage was delivered late at Boston. This delay made me miss my connection from Boston to Hyderabad

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 $52 on Spirit Airlines. Other airlines that offer cheap prices include Alaska Airlines from $114 and Southwest 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, 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 February 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$133Average$248FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$236Average$362FlexibilityNo cancel feeOn-time75%
DeltaCheapest$237Average$607FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$247Average$386FlexibilityNo cancel feeOn-time63%
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