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$111+ 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 10/22. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — ORD
nov. 1 — nov. 81
sáb. 11/1
sáb. 11/8
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 octubre 2, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$284
(Southwest)

One-way from

$111
(SmartFares)

Popular in

December

Cheapest in

February

Average price

$362

Good round-trip deal

$382 or less

Good one-way deal

$239 or less
Provider with most accurate pricing for San Francisco-Chicago (CHI) flight deals.
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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. 9% potential increase in price ($36 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in October 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 octubre 2, 2025.

This Southwest deal was found by Cheapflights users on 9/30. 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.
mar. 10/283:40 pmOAK - STL
1 stop5h 30mSouthwest
mar. 11/412:00 pmSTL - OAK
1 stop6h 35mSouthwest
Deal found 9/30$284
This Delta deal was found by Cheapflights users on 10/2. 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.
mié. 10/224:51 pmOAK - STL
1 stop5h 33mDelta
mar. 10/286:50 amSTL - OAK
1 stop7h 00mDelta
Deal found 10/2$289
This Delta deal was found by Cheapflights users on 10/1. 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.
mar. 11/185:55 amOAK - ORD
2 stops8h 57mDelta
jue. 11/2710:10 amORD - OAK
2 stops10h 03mDelta
Deal found 10/1$298
This Southwest deal was found by Cheapflights users on 9/30. 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.
jue. 11/612:25 pmOAK - MDW
1 stop6h 45mSouthwest
sáb. 11/82:05 pmMDW - OAK
Nonstop4h 40mSouthwest
Deal found 9/30$299
This Southwest deal was found by Cheapflights users on 10/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/306:25 amOAK - ORD
2 stops8h 20mSouthwest
lun. 11/32:15 pmORD - OAK
1 stop8h 20mSouthwest
Deal found 10/1$299
This Alaska Airlines deal was found by Cheapflights users on 10/2. 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.
sáb. 11/227:59 pmOAK - ORD
1 stop7h 02mAlaska Airlines
mié. 12/38:00 amORD - OAK
1 stop17h 59mAlaska Airlines
Deal found 10/2$300
This Alaska Airlines deal was found by Cheapflights users on 10/1. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/19:30 amOAK - ORD
2 stops12h 54mAlaska Airlines
lun. 11/37:00 amORD - OAK
1 stop14h 23mAlaska Airlines
Deal found 10/1$301
This Southwest deal was found by Cheapflights users on 9/30. 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.
jue. 12/1812:20 pmOAK - MDW
2 stops7h 35mSouthwest
sáb. 1/177:40 pmMDW - OAK
Nonstop4h 55mSouthwest
Deal found 9/30$302
This Alaska Airlines deal was found by Cheapflights users on 10/1. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/36:40 amOAK - ORD
1 stop15h 19mAlaska Airlines
dom. 12/76:00 amORD - OAK
1 stop19h 59mAlaska Airlines
Deal found 10/1$302
This Southwest deal was found by Cheapflights users on 9/29. 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.
vie. 10/2411:35 amOAK - MDW
1 stop6h 50mSouthwest
mié. 10/299:20 amMDW - OAK
2 stops7h 55mSouthwest
Deal found 9/29$303
This Southwest deal was found by Cheapflights users on 10/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 11/125:40 amOAK - ORD
1 stop7h 45mSouthwest
dom. 11/162:15 pmORD - OAK
1 stop10h 30mSouthwest
Deal found 10/1$303
This Southwest deal was found by Cheapflights users on 9/30. 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.
sáb. 12/66:00 amOAK - MDW
2 stops8h 40mSouthwest
lun. 12/84:05 pmMDW - OAK
Nonstop4h 35mSouthwest
Deal found 9/30$304

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 octubre 2, 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

OaklandSt. Louis

OAK - STL

OAKSTL

Oakland

mar. 11/18

5:55 am-1:31 pm

1 stop5h 36m

Lambert-St Louis

mié. 11/19

6:34 am-11:48 am

1 stop7h 14m

$289

OaklandSt. Louis

OAK - STL

OAKSTL

Oakland

mié. 10/22

4:51 pm-12:24 am

1 stop5h 33m

Lambert-St Louis

mar. 10/28

6:50 am-11:50 am

1 stop7h 00m

$289

OaklandSt. Louis

OAK - STL

OAKSTL

Oakland

mar. 11/18

1:40 pm-9:35 pm

1 stop5h 55m

Lambert-St Louis

mié. 11/19

10:25 am-3:45 pm

2 stops7h 20m

$294

OaklandChicago

OAK - ORD

OAKORD

Oakland

sáb. 11/22

7:59 pm-5:01 am

1 stop7h 02m

Chicago O'Hare Intl

mié. 12/3

8:00 am-10:41 am

1 stop28h 41m

$300

OaklandChicago

OAK - MDW

OAKMDW

Oakland

vie. 10/24

11:35 am-8:25 pm

1 stop6h 50m

Chicago Midway

mié. 10/29

9:20 am-3:15 pm

2 stops7h 55m

$303

OaklandChicago

OAK - ORD

OAKORD

Oakland

lun. 2/23

6:45 pm-1:04 pm

1 stop16h 19m

Chicago O'Hare Intl

sáb. 2/28

2:00 pm-11:38 pm

1 stop11h 38m

$303

OaklandChicago

OAK - ORD

OAKORD

Oakland

vie. 10/24

10:10 am-9:30 pm

1 stop9h 20m

Chicago O'Hare Intl

mié. 10/29

7:00 am-2:30 pm

2 stops9h 30m

$303

OaklandSt. Louis

OAK - STL

OAKSTL

Oakland

mié. 11/19

1:40 pm-11:10 pm

1 stop7h 30m

Lambert-St Louis

jue. 11/20

1:50 pm-6:40 pm

1 stop6h 50m

$309

OaklandChicago

OAK - MDW

OAKMDW

Oakland

jue. 11/6

12:25 pm-9:10 pm

1 stop6h 45m

Chicago Midway

dom. 11/9

6:05 am-11:15 am

1 stop7h 10m

$321

OaklandChicago

OAK - ORD

OAKORD

Oakland

mié. 11/26

5:15 am-2:45 pm

1 stop7h 30m

Chicago O'Hare Intl

mar. 12/2

7:15 am-1:00 pm

1 stop7h 45m

$321

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/30

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 octubre 2, 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 octubre 2, 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
10,994 reviews

Comfort

7.8

Entertainment

7.0

Crew

8.5

Overall

8.0

Boarding

8.1

Food

7.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Alaska Airlines
8.0
Very good
10,994 reviews
Alaska Airlines
8.0
Very good
10,994 reviews

Comfort

7.8

Entertainment

7.0

Crew

8.5

Overall

8.0

Boarding

8.1

Food

7.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Southwest
8.0
Very good
4,248 reviews
Alaska Airlines
8.0
Very good
10,994 reviews

Comfort

7.8

Entertainment

7.0

Crew

8.5

Overall

8.0

Boarding

8.1

Food

7.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Delta
8.0
Very good
7,962 reviews
Alaska Airlines
8.0
Very good
10,994 reviews

Comfort

7.8

Entertainment

7.0

Crew

8.5

Overall

8.0

Boarding

8.1

Food

7.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
United Airlines
7.4
Good
8,933 reviews
Alaska Airlines
8.0
Very good
10,994 reviews

Comfort

7.8

Entertainment

7.0

Crew

8.5

Overall

8.0

Boarding

8.1

Food

7.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Spirit Airlines
6.3
Okay
8,070 reviews
Alaska Airlines
8.0
Very good
10,994 reviews

Comfort

7.8

Entertainment

7.0

Crew

8.5

Overall

8.0

Boarding

8.1

Food

7.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.

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.

  • How long is the flight from Oakland, California to Illinois?

    There are many flights that can get you from Oakland, California to Illinois in 5h 36m. Fly via Delta, Southwest, or Alaska Airlines to get the fastest option. The distance from Oakland, California to Illinois is about 1720 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Oakland, California to Illinois one-way?

    To fly one-way, consider booking your trip with Alaska Airlines, which is currently one of the cheapest options available, starting at $126. Southwest flights start at $127 while deals on Delta start at $127 one-way.

  • 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.

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Alternative routes for Oakland to Illinois

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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 octubre 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$108Average$220FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$163Average$287FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$189Average$356FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$242Average$417FlexibilityNo cancel feeOn-time63%

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