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$128+ 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 1/21. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — ORD
Dec 17 — Dec 241
Wed 12/17
Wed 12/24
1 adult, Economy
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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 November 17, 2025.

This KAYAK deal was found by Cheapflights users on 11/15. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/32:31 pmOAK - ORD
1 stop7h 28mAlaska Airlines
Tue 12/93:35 pmORD - OAK
1 stop10h 24mAlaska Airlines
Deal found 11/15$271
This Southwest deal was found by Cheapflights users on 11/15. 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.
Sun 12/75:25 amOAK - MDW
Nonstop4h 05mSouthwest
Tue 12/93:10 pmMDW - OAK
1 stop6h 55mSouthwest
Deal found 11/15$277
This Delta deal was found by Cheapflights users on 11/15. 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 12/1312:30 pmOAK - ORD
1 stop6h 51mDelta
Wed 12/177:40 pmORD - OAK
1 stop6h 28mDelta
Deal found 11/15$277
This Delta deal was found by Cheapflights users on 11/17. 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 12/34:50 pmOAK - ORD
2 stops13h 49mDelta
Sat 12/65:29 pmORD - OAK
1 stop6h 31mDelta
Deal found 11/17$280
This KAYAK deal was found by Cheapflights users on 11/17. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/32:31 pmOAK - ORD
1 stop7h 28mAlaska Airlines
Mon 12/85:51 pmORD - OAK
1 stop8h 08mAlaska Airlines
Deal found 11/17$282
This Delta deal was found by Cheapflights users on 11/17. 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 12/35:55 amOAK - MDW
2 stops10h 23mDelta
Sat 12/61:14 pmMDW - OAK
2 stops10h 46mDelta
Deal found 11/17$285
This Cheapflightsfares deal was found by Cheapflights users on 11/16. 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 12/132:31 pmOAK - ORD
1 stop7h 28mAlaska Airlines
Mon 12/155:51 pmORD - OAK
1 stop8h 08mAlaska Airlines
Deal found 11/16$286
This Southwest deal was found by Cheapflights users on 11/17. 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.
Mon 12/87:55 amOAK - MDW
1 stop6h 15mSouthwest
Tue 12/98:20 amMDW - OAK
1 stop8h 25mSouthwest
Deal found 11/17$287
This Southwest deal was found by Cheapflights users on 11/15. 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 12/35:25 amOAK - ORD
1 stop6h 05mSouthwest
Fri 12/124:25 pmORD - OAK
1 stop8h 35mSouthwest
Deal found 11/15$287
This Southwest deal was found by Cheapflights users on 11/17. 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 12/265:25 amOAK - MDW
Nonstop4h 05mSouthwest
Sun 1/117:55 amMDW - OAK
1 stop6h 40mSouthwest
Deal found 11/17$289
This Alaska Airlines deal was found by Cheapflights users on 11/16. 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.
Fri 12/126:40 amOAK - ORD
1 stop8h 15mAlaska Airlines
Sat 12/138:00 amORD - OAK
1 stop28h 41mAlaska Airlines
Deal found 11/16$289
This Southwest deal was found by Cheapflights users on 11/17. 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 11/273:30 pmOAK - MDW
1 stop11h 35mSouthwest
Sat 12/62:05 pmMDW - OAK
Nonstop4h 40mSouthwest
Deal found 11/17$292

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 November 17, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$255
(Southwest)

One-way from

$128
(Southwest)

Popular in

November

Cheapest in

February

Average price

$482

Good round-trip deal

$483 or less

Good one-way deal

$203 or less
Provider with most accurate pricing for San Francisco-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for San Francisco-Chicago (CHI) flights.
Search Deals
From Oakland to Illinois
Search Deals
One-way flight from Oakland to Illinois
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($80 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a round-trip flight from Oakland to Illinois.
Search Deals
Price to beat on a one-way flight from Oakland to Illinois.
Search Deals

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 November 17, 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 - MDW

OAKMDW

Oakland

Wed 1/7

11:10 am-5:15 pm

Nonstop4h 05m

Chicago Midway

Sat 1/10

7:40 pm-10:35 pm

Nonstop4h 55m

$267

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 1/14

5:55 am-1:38 pm

1 stop5h 43m

Chicago O'Hare Intl

Sat 1/17

7:20 am-11:57 am

1 stop6h 37m

$275

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Thu 1/1

7:45 am-4:55 pm

1 stop7h 10m

Chicago Midway

Sat 1/10

7:40 pm-10:35 pm

Nonstop4h 55m

$277

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sat 12/13

12:30 pm-9:21 pm

1 stop6h 51m

Chicago O'Hare Intl

Wed 12/17

7:40 pm-12:08 am

1 stop6h 28m

$277

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Sun 12/7

5:25 am-11:30 am

Nonstop4h 05m

Chicago Midway

Tue 12/9

4:05 pm-6:40 pm

Nonstop4h 35m

$279

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Wed 12/10

11:00 am-5:05 pm

Nonstop4h 05m

Chicago Midway

Thu 12/11

4:05 pm-6:40 pm

Nonstop4h 35m

$279

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 1/14

10:20 am-10:35 pm

2 stops10h 15m

Chicago O'Hare Intl

Sat 1/17

7:15 am-1:30 pm

1 stop8h 15m

$280

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 3/3

6:15 am-4:33 pm

1 stop8h 18m

Chicago O'Hare Intl

Wed 3/4

7:00 am-4:37 pm

1 stop11h 37m

$281

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 1/8

8:10 am-11:50 pm

1 stop13h 40m

Chicago O'Hare Intl

Mon 1/12

3:35 pm-4:23 pm

1 stop26h 48m

$283

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 1/7

5:55 am-1:38 pm

1 stop5h 43m

Chicago O'Hare Intl

Fri 1/9

2:20 pm-10:53 pm

2 stops10h 33m

$284

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/15

Showing 1-10 of 59 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, December is the cheapest month in which you can book a flight from Oakland, California to Illinois (average of $110). Flying from Oakland, California to Illinois in March is currently the most expensive (average of $194). 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 November 17, 2025.

When flying from Oakland, California to Illinois, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 43% versus a flight at noon.

What is the cheapest day to fly from Oakland, California to Illinois?

Use this chart to determine the cheapest time to fly round-trip from Oakland to Illinois. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Oakland, California to Illinois flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Tuesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 November 17, 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
11,312 reviews

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Food

7.1

Overall

8.0

Crew

8.5

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
11,312 reviews
Alaska Airlines
8.0
Very good
11,312 reviews

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Food

7.1

Overall

8.0

Crew

8.5

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
4,244 reviews
Alaska Airlines
8.0
Very good
11,312 reviews

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Food

7.1

Overall

8.0

Crew

8.5

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
7.9
Good
8,006 reviews
Alaska Airlines
8.0
Very good
11,312 reviews

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Food

7.1

Overall

8.0

Crew

8.5

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
9,014 reviews
Alaska Airlines
8.0
Very good
11,312 reviews

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Food

7.1

Overall

8.0

Crew

8.5

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
8,144 reviews
Alaska Airlines
8.0
Very good
11,312 reviews

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Food

7.1

Overall

8.0

Crew

8.5

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 4h 05m. Fly via Southwest, Delta, or Alaska Airlines to get the fastest option. The distance from Oakland, California to Illinois is about 1839 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 $137. Southwest flights start at $138 while deals on Delta start at $138 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, December is the cheapest month in which you can book a flight from Oakland, California to Illinois (average of $110). Flying from Oakland, California to Illinois in March is currently the most expensive (average of $194). 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 November 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$108Average$220FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$163Average$359FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$189Average$356FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$246Average$427FlexibilityNo cancel feeOn-time63%

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