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$56+ 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 7/1. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — ORD
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$204
(Southwest)

One-way from

$56
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$354

Good round-trip deal

$364 or less

Good one-way deal

$228 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 ($21 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 June 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 June 12, 2025.

This Southwest deal was found by Cheapflights users on 6/10. 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 6/302:05 pmOAK - ORD
1 stop7h 35mSouthwest
Fri 7/46:15 amORD - OAK
2 stops10h 10mSouthwest
Deal found 6/10$204
This Cheapflightsfares deal was found by Cheapflights users on 6/10. 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.
Wed 9/101:08 pmOAK - ORD
2 stops8h 35mSpirit Airlines
Mon 9/226:00 amORD - OAK
2 stops8h 13mSpirit Airlines
Deal found 6/10$205
This Alaska Airlines deal was found by Cheapflights users on 6/10. 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.
Tue 8/52:38 pmOAK - ORD
1 stop7h 21mAlaska Airlines
Wed 8/66:00 amORD - OAK
1 stop9h 43mAlaska Airlines
Deal found 6/10$216
This Southwest deal was found by Cheapflights users on 6/10. 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 7/79:15 pmOAK - MDW
1 stop5h 45mSouthwest
Sat 7/127:50 amMDW - OAK
1 stop6h 15mSouthwest
Deal found 6/10$227
This Booking.com deal was found by Cheapflights users on 6/10. 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.
Thu 7/106:00 amOAK - ORD
1 stop6h 13mMultiple Airlines
Thu 7/176:00 amORD - OAK
1 stop13h 15mMultiple Airlines
Deal found 6/10$236
This Mytrip deal was found by Cheapflights users on 6/10. 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 6/259:38 pmOAK - STL
2 stops34h 55mMultiple Airlines
Sun 6/296:12 amSTL - OAK
1 stop12h 33mMultiple Airlines
Deal found 6/10$256
This Delta deal was found by Cheapflights users on 6/11. 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 8/912:30 pmOAK - ORD
1 stop7h 38mDelta
Wed 8/137:45 amORD - OAK
1 stop6h 10mDelta
Deal found 6/11$257
This Delta deal was found by Cheapflights users on 6/11. 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 7/224:55 pmOAK - MDW
2 stops13h 49mDelta
Tue 7/2912:43 pmMDW - OAK
2 stops13h 12mDelta
Deal found 6/11$267
This Mytrip deal was found by Cheapflights users on 6/12. 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.
Thu 7/106:00 amOAK - STL
2 stops25h 52mSpirit Airlines
Thu 7/1710:47 amSTL - OAK
2 stops38h 46mSpirit Airlines
Deal found 6/12$269
This Mytrip deal was found by Cheapflights users on 6/11. 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.
Thu 8/76:00 amOAK - RFD
2 stops28h 10mMultiple Airlines
Sun 8/1012:44 pmRFD - OAK
1 stop21h 44mMultiple Airlines
Deal found 6/11$316
This Southwest deal was found by Cheapflights users on 6/10. 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 7/239:15 amOAK - STL
1 stop7h 40mSouthwest
Tue 7/295:35 amSTL - OAK
1 stop6h 20mSouthwest
Deal found 6/10$319
This Delta deal was found by Cheapflights users on 6/10. 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 11/65:05 pmOAK - STL
1 stop5h 32mDelta
Tue 11/116:59 pmSTL - OAK
1 stop6h 54mDelta
Deal found 6/10$328

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 June 12, 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

Mon 6/30

2:05 pm-11:40 pm

1 stop7h 35m

Chicago O'Hare Intl

Fri 7/4

6:15 am-2:25 pm

2 stops10h 10m

$204

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 9/10

1:08 pm-11:43 pm

2 stops8h 35m

Chicago O'Hare Intl

Mon 9/22

6:00 am-12:13 pm

2 stops8h 13m

$205

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 8/5

2:38 pm-11:59 pm

1 stop7h 21m

Chicago O'Hare Intl

Wed 8/6

6:00 am-1:43 pm

1 stop9h 43m

$216

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Mon 7/7

9:15 pm-5:00 am

1 stop5h 45m

Chicago Midway

Sat 7/12

7:50 am-12:05 pm

1 stop6h 15m

$227

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 7/10

6:00 am-2:13 pm

1 stop6h 13m

Chicago O'Hare Intl

Thu 7/17

6:00 am-5:15 pm

1 stop13h 15m

$236

OaklandSt. Louis

OAK - STL

OAKSTL

Oakland

Wed 6/25

9:38 pm-10:33 am

2 stops34h 55m

Lambert-St Louis

Sun 6/29

6:12 am-4:45 pm

1 stop12h 33m

$256

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sat 8/9

12:30 pm-10:08 pm

1 stop7h 38m

Chicago O'Hare Intl

Wed 8/13

7:45 am-11:55 am

1 stop6h 10m

$257

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Tue 7/22

4:55 pm-8:44 am

2 stops13h 49m

Chicago Midway

Tue 7/29

12:43 pm-11:55 pm

2 stops13h 12m

$267

OaklandSt. Louis

OAK - STL

OAKSTL

Oakland

Thu 7/10

6:00 am-9:52 am

2 stops25h 52m

Lambert-St Louis

Thu 7/17

10:47 am-11:33 pm

2 stops38h 46m

$269

OaklandChicago

OAK - RFD

OAKRFD

Oakland

Thu 8/7

6:00 am-12:10 pm

2 stops28h 10m

Chicago Greater Rockford

Sun 8/10

12:44 pm-8:28 am

1 stop21h 44m

$316

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 35 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 June 12, 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.

Rainfall in Illinois by month

Plan your trip to Illinois by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Illinois ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Illinois when rainfall is around 1.7 in.

Temperature in Illinois by month

Plan your trip to Illinois by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Illinois, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 June 12, 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

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.1

Crew

8.5

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

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.1

Crew

8.5

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
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.1

Crew

8.5

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
7,950 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.9
Good
2,494 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.1

Crew

8.5

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
345 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.1

Crew

8.5

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 cheapest airlines to fly from Oakland, California to Illinois one-way?

    To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $56. Southwest flights start at $95 while deals on Sun Country Air start at $111 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.

See more FAQs

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Alternative routes for Oakland to Illinois

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Top 5 airlines flying from Oakland to Illinois

Discover the top 5 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$108Average$262FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$138Average$356FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$163Average$257FlexibilityNo cancel feeOn-time69%
DeltaCheapest$236Average$360FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$263Average$418FlexibilityNo cancel feeOn-time63%

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