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Illinois

$119+ 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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — ORD
mai 3 — mai 101
dim. 5/3
dim. 5/10
1 adult, Economy
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Cheap 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 avril 3, 2026.

This Southwest deal was found by Cheapflights users on 3/31. 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.
mer. 4/2211:55 pm
OAK
-
MDW
Nonstop4h 05m
Southwest
mar. 4/2810:00 am
MDW
-
OAK
Nonstop4h 35m
Southwest
Deal found 3/31$237
This Southwest deal was found by Cheapflights users on 4/1. 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.
mer. 4/295:50 am
OAK
-
MDW
Nonstop4h 05m
Southwest
mer. 5/610:10 am
MDW
-
OAK
1 stop6h 50m
Southwest
Deal found 4/1$247
This Southwest deal was found by Cheapflights users on 4/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/55:50 am
OAK
-
MDW
Nonstop4h 05m
Southwest
jeu. 5/79:50 pm
MDW
-
OAK
Nonstop4h 35m
Southwest
Deal found 4/2$251
This CheapOair deal was found by Cheapflights users on 4/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 5/67:19 pm
OAK
-
ORD
1 stop26h 24m
Alaska Airlines
lun. 5/117:59 pm
ORD
-
OAK
1 stop20h 39m
Alaska Airlines
Deal found 4/1$255
This Southwest deal was found by Cheapflights users on 3/31. 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.
mer. 5/208:15 am
OAK
-
MDW
1 stop6h 45m
Southwest
mer. 5/272:55 pm
MDW
-
OAK
1 stop7h 40m
Southwest
Deal found 3/31$257
This Southwest deal was found by Cheapflights users on 3/31. 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.
mer. 4/2210:15 am
OAK
-
ORD
1 stop6h 35m
Southwest
mar. 4/284:50 pm
ORD
-
OAK
1 stop7h 45m
Southwest
Deal found 3/31$257
This Southwest deal was found by Cheapflights users on 4/3. 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.
mer. 5/1311:55 pm
OAK
-
MDW
Nonstop4h 05m
Southwest
sam. 5/166:45 am
MDW
-
OAK
1 stop7h 25m
Southwest
Deal found 4/3$260
This Southwest deal was found by Cheapflights users on 3/30. 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.
lun. 4/2711:55 pm
OAK
-
MDW
Nonstop4h 05m
Southwest
jeu. 4/309:50 pm
MDW
-
OAK
Nonstop4h 35m
Southwest
Deal found 3/30$265
This Alaska Airlines deal was found by Cheapflights users on 4/2. 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.
mar. 4/286:20 am
OAK
-
ORD
1 stop8h 36m
Alaska Airlines
mer. 4/293:52 pm
ORD
-
OAK
1 stop8h 31m
Alaska Airlines
Deal found 4/2$270
This Alaska Airlines deal was found by Cheapflights users on 4/1. 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.
mar. 4/2810:57 am
OAK
-
ORD
1 stop24h 16m
Alaska Airlines
lun. 5/47:59 pm
ORD
-
OAK
1 stop16h 18m
Alaska Airlines
Deal found 4/1$271
This CheapOair deal was found by Cheapflights users on 4/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 6/18:13 pm
OAK
-
ORD
1 stop15h 01m
Alaska Airlines
jeu. 6/186:20 am
ORD
-
OAK
1 stop9h 50m
Alaska Airlines
Deal found 4/1$273
This CheapOair deal was found by Cheapflights users on 4/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 6/102:50 pm
OAK
-
ORD
1 stop6h 46m
Alaska Airlines
mer. 7/87:59 pm
ORD
-
OAK
1 stop15h 58m
Alaska Airlines
Deal found 4/1$274

Find flight deals from Oakland to Illinois

Keep the following information in mind while searching for Oakland to Illinois flight deals. Data was last updated avril 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$237
(Southwest)

One-way from

$119
(Southwest)

Popular in

March

Cheapest in

September

Average price

$333

Good round-trip deal

$383 or less

Good one-way deal

$199 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. 2% potential increase in price ($8 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
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 avril 3, 2026.
Use the filters below to find and compare flights from Oakland to Illinois that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

OaklandChicago

OAK - MDW

OAKMDW

Oakland

lun. 4/27

8:30 pm-4:35 am

1 stop6h 05m

Chicago Midway

jeu. 4/30

9:50 pm-12:25 am

Nonstop4h 35m

$275

OaklandChicago

OAK - ORD

OAKORD

Oakland

mar. 5/5

12:25 pm-10:55 pm

2 stops8h 30m

Chicago O'Hare Intl

jeu. 5/7

7:20 pm-12:05 am

1 stop6h 45m

$276

OaklandChicago

OAK - ORD

OAKORD

Oakland

mar. 4/28

6:20 am-4:56 pm

1 stop8h 36m

Chicago O'Hare Intl

mer. 4/29

3:52 pm-10:23 pm

1 stop8h 31m

$285

OaklandChicago

OAK - MDW

OAKMDW

Oakland

mer. 5/6

6:00 am-3:55 pm

1 stop7h 55m

Chicago Midway

sam. 5/9

1:00 pm-6:45 pm

1 stop7h 45m

$285

OaklandChicago

OAK - MDW

OAKMDW

Oakland

mar. 4/21

5:55 am-5:58 pm

2 stops10h 03m

Chicago Midway

sam. 4/25

9:27 am-4:26 pm

2 stops8h 59m

$301

OaklandChicago

OAK - ORD

OAKORD

Oakland

mar. 5/12

8:10 pm-5:05 am

1 stop6h 55m

Chicago O'Hare Intl

mar. 5/19

2:10 pm-11:50 pm

1 stop11h 40m

$313

OaklandChicago

OAK - MDW

OAKMDW

Oakland

ven. 5/29

11:55 pm-6:00 am

Nonstop4h 05m

Chicago Midway

mar. 6/2

3:55 pm-8:20 pm

1 stop6h 25m

$324

OaklandChicago

OAK - ORD

OAKORD

Oakland

dim. 4/26

6:20 am-4:56 pm

1 stop8h 36m

Chicago O'Hare Intl

jeu. 4/30

3:52 pm-10:23 pm

1 stop8h 31m

$328

OaklandChicago

OAK - MDW

OAKMDW

Oakland

mer. 5/6

6:10 am-2:10 pm

1 stop6h 00m

Chicago Midway

dim. 5/10

6:00 am-12:35 pm

1 stop8h 35m

$328

OaklandChicago

OAK - MDW

OAKMDW

Oakland

jeu. 9/24

5:20 am-11:25 am

Nonstop4h 05m

Chicago Midway

lun. 9/28

3:55 pm-9:10 pm

1 stop7h 15m

$350

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/3

Showing 1-10 of 60 resultsSorted by cheapest first
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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, April is the cheapest month in which you can book a flight from Oakland, California to Illinois (average of $120). Flying from Oakland, California to Illinois in December is currently the most expensive (average of $233). 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 avril 3, 2026.

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 57% versus a flight at noon.

How much does it cost to fly round-trip from Oakland, California to Illinois?

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 avril 3, 2026.
Get a feel of what it's like to fly with Southwest,Alaska Airlines, andUnited 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
8.0
Very good
4,343 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Southwest
8.0
Very good
4,343 reviews
Southwest
8.0
Very good
4,343 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Alaska Airlines
7.9
Good
12,161 reviews
Southwest
8.0
Very good
4,343 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
United Airlines
7.4
Good
9,543 reviews
Southwest
8.0
Very good
4,343 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Spirit Airlines
6.3
Okay
8,583 reviews
Southwest
8.0
Very good
4,343 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.

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 6h 05m. Fly via Southwest, Alaska Airlines, or Delta 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 Spirit Airlines, which is currently one of the cheapest options available, starting at $84. Southwest flights start at $99 while deals on Delta start at $128 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, April is the cheapest month in which you can book a flight from Oakland, California to Illinois (average of $120). Flying from Oakland, California to Illinois in December is currently the most expensive (average of $233). 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 avril 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$108Average$222FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$163Average$359FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$237Average$522FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$246Average$424FlexibilityNo cancel feeOn-time63%

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