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$51+ Cheap flights from Oakland, CA (OAK) to Illinois

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 9/10. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — ORD
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheap flight deals from Oakland to Illinois

Keep the following information in mind while searching for Oakland to Illinois flight deals. Data was last updated August 14, 2025.

Round-trip from

$205
(CheapOair)

One-way from

$51
(Cheapflightsfares)

Popular in

December

Cheapest in

February

Average price

$366

Good round-trip deal

$342 or less

Good one-way deal

$189 or less
From Oakland to Illinois
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One-way flight from Oakland to Illinois
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Highest demand for flights based on searches. 6% potential increase in price ($25 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Oakland to Illinois.
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Price to beat on a one-way flight from Oakland to Illinois.
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Find flight deals from Oakland to Illinois

Cheapest flights from Oakland to Illinois
Explore the most affordable flight options available from Oakland to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 14, 2025.

This CheapOair deal was found by Cheapflights users on 8/14. 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 9/1010:56 amOAK - ORD
2 stops8h 36mSpirit Airlines
Sat 9/2012:46 pmORD - OAK
1 stop12h 46mSpirit Airlines
Deal found 8/14$205
This FlightHub deal was found by Cheapflights users on 8/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/310:44 amOAK - ORD
2 stops16h 06mSpirit Airlines
Fri 9/56:05 pmORD - OAK
2 stops17h 56mSpirit Airlines
Deal found 8/13$206
This Mytrip deal was found by Cheapflights users on 8/13. 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 8/2710:44 amOAK - ORD
2 stops16h 06mSpirit Airlines
Wed 9/107:09 pmORD - OAK
2 stops20h 25mSpirit Airlines
Deal found 8/13$207
This CheapOair deal was found by Cheapflights users on 8/12. 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.
Fri 9/56:30 amOAK - ORD
1 stop13h 02mSpirit Airlines
Mon 9/86:05 pmORD - OAK
1 stop7h 27mSpirit Airlines
Deal found 8/12$208
This Kiwi.com deal was found by Cheapflights users on 8/12. 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.
Fri 10/248:33 amOAK - ORD
1 stop10h 21mMultiple Airlines
Mon 10/279:54 pmORD - OAK
1 stop11h 44mMultiple Airlines
Deal found 8/12$209
This CheapOair deal was found by Cheapflights users on 8/12. 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 9/1710:56 amOAK - ORD
2 stops8h 36mSpirit Airlines
Sun 9/218:01 pmORD - OAK
2 stops16h 00mSpirit Airlines
Deal found 8/12$210
This Mytrip deal was found by Cheapflights users on 8/13. 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 9/310:44 amOAK - ORD
2 stops16h 06mSpirit Airlines
Tue 9/162:04 pmORD - OAK
3 stops21h 57mSpirit Airlines
Deal found 8/13$212
This CheapOair deal was found by Cheapflights users on 8/12. 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 9/310:44 amOAK - ORD
2 stops16h 06mSpirit Airlines
Tue 9/911:15 amORD - OAK
1 stop14h 17mSpirit Airlines
Deal found 8/12$213
This Mytrip deal was found by Cheapflights users on 8/12. 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 9/610:56 amOAK - ORD
2 stops22h 55mSpirit Airlines
Sun 9/78:01 pmORD - OAK
2 stops16h 00mSpirit Airlines
Deal found 8/12$214
This FlightHub deal was found by Cheapflights users on 8/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/146:00 amOAK - ORD
1 stop6h 27mSpirit Airlines
Tue 10/216:40 amORD - OAK
1 stop16h 56mSpirit Airlines
Deal found 8/13$215
This Kiwi.com deal was found by Cheapflights users on 8/12. 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.
Thu 9/186:30 amOAK - ORD
1 stop13h 02mMultiple Airlines
Fri 9/199:54 pmORD - OAK
1 stop17h 40mMultiple Airlines
Deal found 8/12$216
This Southwest deal was found by Cheapflights users on 8/13. 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 11/75:25 amOAK - MDW
Nonstop4h 05mSouthwest
Tue 11/115:30 amMDW - OAK
1 stop6h 20mSouthwest
Deal found 8/13$217

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oakland to Illinois 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 August 14, 2025.
Use the filters below to find and compare flights from Oakland to Illinois that are best for you.

Fly from

Oakland

Fly to

Illinois

Route

Depart

Return

Price

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 9/10

6:30 am-6:51 pm

1 stop10h 21m

Chicago O'Hare Intl

Thu 9/11

9:00 am-1:34 pm

1 stop6h 34m

$205

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 9/10

10:56 am-9:32 pm

2 stops8h 36m

Chicago O'Hare Intl

Sat 9/20

12:46 pm-11:32 pm

1 stop12h 46m

$205

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 9/2

6:00 am-5:15 pm

1 stop9h 15m

Chicago O'Hare Intl

Thu 9/4

8:01 pm-10:01 am

2 stops16h 00m

$205

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 9/18

6:30 am-9:32 pm

1 stop13h 02m

Chicago O'Hare Intl

Tue 9/23

9:00 am-1:34 pm

1 stop6h 34m

$205

OaklandChicago

OAK - ORD

OAKORD

Oakland

Fri 9/26

6:30 am-4:59 pm

1 stop8h 29m

Chicago O'Hare Intl

Tue 9/30

9:00 am-1:34 pm

1 stop6h 34m

$205

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sat 9/20

6:30 am-9:32 pm

1 stop13h 02m

Chicago O'Hare Intl

Tue 9/23

9:00 am-1:34 pm

1 stop6h 34m

$206

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 9/3

10:44 am-4:50 am

2 stops16h 06m

Chicago O'Hare Intl

Fri 9/5

6:05 pm-10:01 am

2 stops17h 56m

$206

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 9/25

6:30 am-9:32 pm

1 stop13h 02m

Chicago O'Hare Intl

Mon 9/29

9:00 am-1:34 pm

1 stop6h 34m

$206

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 9/24

6:30 am-9:32 pm

1 stop13h 02m

Chicago O'Hare Intl

Mon 9/29

9:00 am-1:34 pm

1 stop6h 34m

$206

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 8/27

10:44 am-4:50 am

2 stops16h 06m

Chicago O'Hare Intl

Wed 9/10

7:09 pm-1:34 pm

2 stops20h 25m

$207

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 60 results
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Best time to book a flight from Oakland to Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois from Oakland 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 Oakland to Illinois

What is the cheapest month to book a flight from Oakland, California to Illinois?

Currently, August is the cheapest month in which you can book a flight from Oakland, California to Illinois (average of $245). Flying from Oakland, California to Illinois in March is currently the most expensive (average of $321). 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 OAK to IL?

Find hourly flight availability from Oakland to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 14, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Oakland, California to Illinois as you normally would.

Reviews of airlines servicing Illinois

Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated August 14, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest, and Delta from Oakland to Illinois by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Entertainment

7.0

Crew

8.5

Comfort

7.8

Boarding

8.1

Food

7.1

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

Overall

8.0

Entertainment

7.0

Crew

8.5

Comfort

7.8

Boarding

8.1

Food

7.1

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
4,244 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Entertainment

7.0

Crew

8.5

Comfort

7.8

Boarding

8.1

Food

7.1

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
7,980 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Entertainment

7.0

Crew

8.5

Comfort

7.8

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,916 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Entertainment

7.0

Crew

8.5

Comfort

7.8

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Spirit Airlines
6.3
Okay
8,046 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Entertainment

7.0

Crew

8.5

Comfort

7.8

Boarding

8.1

Food

7.1

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 Oakland to Illinois. 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 from for flights from Oakland to Illinois?

    Most people fly from Oakland (OAK) if they book a flight from Oakland to Illinois. Oakland is conveniently located just 7.0 mi from Oakland’s city center.

  • What are the most popular routes from Oakland, California to Illinois?

    When deciding which route to take from Oakland, California to Illinois consider Oakland - Chicago O'Hare Intl, Oakland - Chicago Midway or Oakland - Lambert-St Louis as they are the most popular.

  • Can I find deals for flights from Oakland to Illinois that include hotel bookings?

    Yes. In addition to deals on Oakland to Illinois flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Oakland to Illinois?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Oakland to Illinois.

  • Can I find deals for business class flights from Oakland to Illinois?

    Yes. Cheapflights offers flight deals from Oakland to Illinois 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 Oakland, California to Illinois?

    Currently, August is the cheapest month in which you can book a flight from Oakland, California to Illinois (average of $245). Flying from Oakland, California to Illinois in March is currently the most expensive (average of $321). 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 Oakland to Illinois

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Oakland to Illinois

Discover the top 4 airlines that operate flights from Oakland to Illinois. 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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$100Average$219FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$138Average$356FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$163Average$287FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$242Average$403FlexibilityNo cancel feeOn-time63%

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