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$61+ 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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — ORD
ene. 26 — feb. 21
dom. 1/26
dom. 2/2
1 adult, Economy
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Cheap flight deals from Oakland to Illinois

Discover tips and strategies to find the most affordable flight options for your journey from Oakland (OAK) to Illinois (USIL). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated enero 21, 2025.

Round-trip from

$131
(Cheapflightsfares)

One-way from

$61
(Booking.com)
From Oakland to Illinois
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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 enero 21, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 1/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 2/1212:40 pmOAK - ORD
1 stop7h 10mSpirit Airlines
mié. 2/191:32 pmORD - OAK
1 stop10h 40mSpirit Airlines
Deal found 1/19$131
This Southwest deal was found by Cheapflights users on 1/19. 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.
dom. 2/98:05 amOAK - ORD
1 stop11h 25mSouthwest
mar. 2/115:45 amORD - OAK
2 stops9h 55mSouthwest
Deal found 1/19$252
This Delta deal was found by Cheapflights users on 1/20. 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.
jue. 2/205:00 pmOAK - STL
1 stop5h 38mDelta
vie. 2/216:59 pmSTL - OAK
1 stop6h 57mDelta
Deal found 1/20$257
This Delta deal was found by Cheapflights users on 1/18. 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. 2/251:15 pmOAK - ORD
1 stop6h 12mDelta
vie. 2/287:18 pmORD - OAK
1 stop6h 38mDelta
Deal found 1/18$257
This Delta deal was found by Cheapflights users on 1/20. 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.
mié. 9/310:45 pmOAK - MDW
2 stops12h 17mDelta
mar. 9/161:05 pmMDW - OAK
1 stop10h 27mDelta
Deal found 1/20$262
This Mytrip deal was found by Cheapflights users on 1/21. 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.
lun. 2/311:37 amOAK - STL
2 stops25h 06mSpirit Airlines
mar. 3/115:38 pmSTL - OAK
3 stops25h 19mSpirit Airlines
Deal found 1/21$268
This Southwest deal was found by Cheapflights users on 1/21. 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. 2/198:35 amOAK - MDW
1 stop6h 20mSouthwest
mié. 2/268:30 amMDW - OAK
1 stop7h 00mSouthwest
Deal found 1/21$272
This Alaska Airlines deal was found by Cheapflights users on 1/19. 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.
mar. 4/86:43 amOAK - ORD
1 stop20h 57mAlaska Airlines
mié. 4/165:53 pmORD - OAK
1 stop7h 50mAlaska Airlines
Deal found 1/19$286
This Mytrip deal was found by Cheapflights users on 1/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 2/1812:40 pmOAK - STL
3 stops26h 05mMultiple Airlines
mar. 2/254:00 pmSTL - OAK
3 stops21h 45mMultiple Airlines
Deal found 1/19$304
This Mytrip deal was found by Cheapflights users on 1/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 1/297:42 amOAK - ORD
2 stops20h 13mMultiple Airlines
lun. 2/311:45 amORD - OAK
3 stops13h 51mMultiple Airlines
Deal found 1/19$308
This Southwest deal was found by Cheapflights users on 1/19. 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.
mar. 2/184:20 pmOAK - STL
1 stop5h 45mSouthwest
mar. 2/253:25 pmSTL - OAK
1 stop6h 20mSouthwest
Deal found 1/19$352
This Alaska Airlines deal was found by Cheapflights users on 1/20. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 4/58:25 pmOAK - STL
2 stops25h 34mAlaska Airlines
mié. 4/96:44 amSTL - OAK
1 stop18h 59mAlaska Airlines
Deal found 1/20$395

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 enero 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

OaklandChicago

OAK - ORD

OAKORD

Oakland

mié. 2/12

12:40 pm-9:50 pm

1 stop7h 10m

Chicago O'Hare Intl

mié. 2/19

1:32 pm-10:12 pm

1 stop10h 40m

$131

OaklandChicago

OAK - ORD

OAKORD

Oakland

dom. 2/9

8:05 am-9:30 pm

1 stop11h 25m

Chicago O'Hare Intl

mar. 2/11

5:45 am-1:40 pm

2 stops9h 55m

$252

OaklandSt. Louis

OAK - STL

OAKSTL

Oakland

jue. 2/20

5:00 pm-12:38 am

1 stop5h 38m

Lambert-St Louis

vie. 2/21

6:59 pm-11:56 pm

1 stop6h 57m

$257

OaklandChicago

OAK - ORD

OAKORD

Oakland

mar. 2/25

1:15 pm-9:27 pm

1 stop6h 12m

Chicago O'Hare Intl

vie. 2/28

7:18 pm-11:56 pm

1 stop6h 38m

$257

OaklandChicago

OAK - MDW

OAKMDW

Oakland

dom. 2/23

6:10 am-12:15 pm

Nonstop4h 05m

Chicago Midway

mar. 2/25

8:30 am-1:30 pm

1 stop7h 00m

$288

OaklandSt. Louis

OAK - STL

OAKSTL

Oakland

mar. 2/18

12:40 pm-4:45 pm

3 stops26h 05m

Lambert-St Louis

mar. 2/25

4:00 pm-11:45 am

3 stops21h 45m

$304

OaklandChicago

OAK - ORD

OAKORD

Oakland

vie. 4/4

7:00 pm-9:44 am

2 stops12h 44m

Chicago O'Hare Intl

mié. 4/9

5:53 pm-11:43 pm

1 stop7h 50m

$308

OaklandChicago

OAK - ORD

OAKORD

Oakland

lun. 3/3

9:46 am-5:53 am

2 stops18h 07m

Chicago O'Hare Intl

sáb. 3/8

5:56 pm-11:43 pm

1 stop7h 47m

$335

OaklandSt. Louis

OAK - STL

OAKSTL

Oakland

mar. 2/18

4:20 pm-12:05 am

1 stop5h 45m

Lambert-St Louis

mar. 2/25

3:25 pm-7:45 pm

1 stop6h 20m

$352

OaklandChicago

OAK - MDW

OAKMDW

Oakland

jue. 3/13

6:00 am-6:18 pm

2 stops10h 18m

Chicago Midway

mar. 3/18

2:55 pm-11:59 pm

2 stops11h 04m

$358

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/19

Showing 1-10 of 28 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.

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 $320). 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 enero 21, 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 enero 21, 2025.
Get a feel of what it's like to fly with Spirit Airlines, Southwest and Alaska Airlines 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
4,659 reviews

Overall

8.1

Entertainment

7.7

Food

7.2

Boarding

8.2

Comfort

8.1

Crew

8.7

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Southwest
8.1
Very good
4,659 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Entertainment

7.7

Food

7.2

Boarding

8.2

Comfort

8.1

Crew

8.7

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Alaska Airlines
8.0
Very good
9,696 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Entertainment

7.7

Food

7.2

Boarding

8.2

Comfort

8.1

Crew

8.7

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Entertainment

7.7

Food

7.2

Boarding

8.2

Comfort

8.1

Crew

8.7

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Spirit Airlines
6.3
Okay
8,113 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Entertainment

7.7

Food

7.2

Boarding

8.2

Comfort

8.1

Crew

8.7

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

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 $61. Southwest flights start at $109 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 $320). 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 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 enero 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$133Average$292FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$138Average$416FlexibilityNo cancel feeOn-time75%
DeltaCheapest$236Average$467FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$262Average$400FlexibilityNo cancel feeOn-time63%
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