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$57+ 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 4/14. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — ORD
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$118
(Expedia)

One-way from

$57
(FlightHub)

Popular in

December

Cheapest in

February

Average price

$297

Good round-trip deal

$406 or less

Good one-way deal

$238 or less
Provider with most accurate pricing for San Francisco-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for San Francisco-Chicago (CHI) flights.
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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. 5% potential increase in price ($19 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 February 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 February 20, 2025.

This CheapOair deal was found by Cheapflights users on 2/19. 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.
Mon 3/105:52 pmOAK - ORD
1 stop10h 50mSpirit Airlines
Wed 3/1210:49 amORD - OAK
1 stop8h 08mSpirit Airlines
Deal found 2/19$118
This Southwest deal was found by Cheapflights users on 2/19. 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.
Tue 5/65:50 amOAK - MDW
Nonstop4h 10mSouthwest
Fri 5/99:10 pmMDW - OAK
Nonstop4h 35mSouthwest
Deal found 2/19$227
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.
Sat 3/156:00 amOAK - ORD
1 stop5h 52mDelta
Tue 3/187:15 pmORD - OAK
1 stop6h 44mDelta
Deal found 2/20$257
This Delta deal was found by Cheapflights users on 2/19. 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.
Fri 9/2610:45 pmOAK - MDW
1 stop8h 33mDelta
Sat 10/41:05 pmMDW - OAK
1 stop10h 27mDelta
Deal found 2/19$288
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/87:30 amOAK - RFD
1 stop11h 16mMultiple Airlines
Sun 5/119:36 pmRFD - OAK
1 stop24h 38mMultiple Airlines
Deal found 2/20$290
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/812:11 pmOAK - STL
3 stops45h 34mMultiple Airlines
Thu 4/106:11 pmSTL - OAK
2 stops14h 38mMultiple Airlines
Deal found 2/20$291
This Orbitz deal was found by Cheapflights users on 2/19. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/286:49 amOAK - ORD
1 stop9h 11mMultiple Airlines
Wed 3/57:47 amORD - OAK
1 stop11h 10mMultiple Airlines
Deal found 2/19$302
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/81:10 pmOAK - STL
1 stop6h 40mSouthwest
Thu 4/107:10 pmSTL - OAK
1 stop6h 35mSouthwest
Deal found 2/20$312
This Alaska Airlines deal was found by Cheapflights users on 2/19. 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.
Thu 4/36:43 amOAK - STL
1 stop15h 16mAlaska Airlines
Mon 4/73:11 pmSTL - OAK
1 stop10h 32mAlaska Airlines
Deal found 2/19$316
This Delta deal was found by Cheapflights users on 2/19. 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 4/306:00 amOAK - STL
1 stop5h 28mDelta
Wed 5/76:59 pmSTL - OAK
1 stop6h 46mDelta
Deal found 2/19$317
This Southwest deal was found by Cheapflights users on 2/19. 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.
Tue 3/115:40 amOAK - ORD
1 stop9h 05mSouthwest
Sat 3/158:00 pmORD - OAK
1 stop6h 30mSouthwest
Deal found 2/19$322
This Delta deal was found by Cheapflights users on 2/19. 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 3/136:00 amOAK - EVV
2 stops8h 49mDelta
Sat 3/156:17 amEVV - OAK
2 stops12h 14mDelta
Deal found 2/19$1,039

Find flights from Oakland to Illinois within your budget

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 February 20, 2025.

Fly from

Oakland

Fly to

Illinois

Route

Depart

Return

Price

OaklandChicago

OAK - ORD

OAKORD

Oakland

Mon 4/7

6:55 pm-6:42 am

1 stop9h 47m

Chicago O'Hare Intl

Wed 4/9

7:41 am-5:34 pm

1 stop11h 53m

$118

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Tue 5/6

5:50 am-12:00 pm

Nonstop4h 10m

Chicago Midway

Fri 5/9

9:10 pm-11:45 pm

Nonstop4h 35m

$227

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 3/25

12:55 pm-9:45 pm

1 stop6h 50m

Chicago O'Hare Intl

Fri 3/28

7:15 pm-11:59 pm

1 stop6h 44m

$253

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 3/27

7:31 am-2:15 pm

3 stops28h 44m

Chicago O'Hare Intl

Tue 4/1

2:34 pm-12:17 pm

2 stops23h 43m

$277

OaklandChicago

OAK - RFD

OAKRFD

Oakland

Thu 5/8

7:30 am-8:46 pm

1 stop11h 16m

Chicago Greater Rockford

Sun 5/11

9:36 pm-8:14 pm

1 stop24h 38m

$290

OaklandSt. Louis

OAK - STL

OAKSTL

Oakland

Tue 4/8

12:11 pm-11:45 am

3 stops45h 34m

Lambert-St Louis

Thu 4/10

6:11 pm-6:49 am

2 stops14h 38m

$291

OaklandSt. Louis

OAK - STL

OAKSTL

Oakland

Tue 4/8

1:10 pm-9:50 pm

1 stop6h 40m

Lambert-St Louis

Thu 4/10

7:10 pm-11:45 pm

1 stop6h 35m

$312

OaklandSt. Louis

OAK - STL

OAKSTL

Oakland

Thu 4/3

6:43 am-11:59 pm

1 stop15h 16m

Lambert-St Louis

Mon 4/7

3:11 pm-11:43 pm

1 stop10h 32m

$316

OaklandSt. Louis

OAK - STL

OAKSTL

Oakland

Wed 4/30

6:00 am-1:28 pm

1 stop5h 28m

Lambert-St Louis

Tue 5/6

7:40 am-12:13 pm

1 stop6h 33m

$317

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Tue 3/18

5:15 pm-9:09 am

2 stops13h 54m

Chicago Midway

Sat 3/29

1:12 pm-10:37 pm

2 stops11h 25m

$358

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 23 results
1
2
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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.

Travel insights for flights from Oakland to Illinois

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

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 February 20, 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 February 20, 2025.
Get a feel of what it's like to fly with Southwest, Alaska Airlines 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.
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Comfort

8.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Comfort

8.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,697 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Comfort

8.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,219 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Comfort

8.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Hawaiian Airlines
7.9
Good
2,317 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Comfort

8.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Sun Country Air
7.0
Good
374 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Comfort

8.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 $57. Southwest flights start at $99 while deals on Delta start at $129 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

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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$130Average$287FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$138Average$377FlexibilityNo cancel feeOn-time75%
DeltaCheapest$235Average$360FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$263Average$406FlexibilityNo cancel feeOn-time63%
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