How many flights depart from Oakland, California to Illinois on average per week?

The number of flights available between Oakland, California and Illinois is 1 per week as of March 2026. The most frequent departure day is Mon, with 100% of weekly flights leaving on this day.

What airlines fly to Illinois?

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Illinois from Oakland, California according to our data. United Airlines is the first choice among our users, with 46% of people opting to fly with this airline when traveling to Illinois. Keep in mind that there are 9 different airlines that fly to Illinois on a routine basis, so you have a few additional options to choose from.

What is the cheapest airline that flies from Oakland to Illinois?

Southwest, Alaska Airlines, and Delta are the most popular carriers operating from Oakland to Illinois

When did momondo last update prices for flights from Oakland Airport to Illinois?

Prices for flights from Oakland Airport to Illinois were last updated today.

How many operators does momondo search for flights from Oakland Airport to Illinois?

The number of operators available for flights from Oakland Airport to Illinois is 5 as of March 2026.

How old do you have to be to fly from Oakland Airport to Illinois?

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Oakland Airport to Illinois.

What documentation or ID do you need to fly to Illinois?

The necessary travel and health documents for your Illinois trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$89 Cheap Flights from Oakland to Illinois in 2026

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Find the cheapest flights from Oakland, California to Illinois

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

11:55 pm - 6:00 am

OAK

MDW

4h 05mnonstop

8:50 pm - 11:25 pm

MDW

OAK

4h 35mnonstop

$177Southwest

Tue, Apr 28 - Wed, Apr 29

5:50 am - 11:55 am

OAK

MDW

4h 05mnonstop

5:35 pm - 10:25 pm

MDW

OAK

6h 50m

1 stop

$187Southwest

Tue, Apr 28 - Wed, Apr 29

6:45 pm - 4:35 am

OAK

MDW

7h 50m

1 stop

5:15 pm - 9:55 pm

MDW

OAK

6h 40m

1 stop

$197Southwest

Tue, Apr 28 - Wed, Apr 29

11:55 pm - 6:00 am

OAK

MDW

4h 05mnonstop

5:55 pm - 8:30 pm

MDW

OAK

4h 35mnonstop

$211Southwest

Tue, Apr 28 - Sat, May 2

2:09 pm - 11:59 pm

OAK

ORD

7h 50m

1 stop

6:00 am - 1:15 pm

ORD

OAK

9h 15m

1 stop

$259Alaska Airlines

Sat, May 2 - Tue, May 5

6:02 am - 11:55 pm

OAK

ORD

15h 53m

1 stop

9:00 am - 6:21 pm

ORD

OAK

11h 21m

1 stop

$266Alaska Airlines

Mon, May 18 - Tue, May 19

12:35 pm - 9:34 pm

OAK

ORD

6h 59m

1 stop

8:55 am - 4:00 pm

ORD

OAK

9h 05m

2 stops

$270Delta

Tue, Mar 31 - Tue, Apr 7

6:20 am - 11:59 pm

OAK

ORD

15h 39m

1 stop

6:00 am - 1:15 pm

ORD

OAK

9h 15m

1 stop

$271Alaska Airlines

Mon, Apr 27 - Wed, Apr 29

4:49 pm - 12:21 am

OAK

STL

5h 32m

1 stop

7:15 am - 11:51 am

STL

OAK

6h 36m

1 stop

$362Delta

Mon, Apr 6 - Tue, Apr 7

5:05 pm - 9:26 am

OAK

EVV

14h 21m

2 stops

1:30 pm - 11:49 pm

EVV

OAK

12h 19m

2 stops

$888Delta

Sat, Jul 25 - Mon, Jul 27

Alaska Airlines flights from Oakland, California to Illinois

Our best Alaska Airlines deals on Oakland, California to Illinois flight tickets

Alaska Airlines

May 2

OAK2:09 pmOakland

7h 50m

1 stop

ORD11:59 pmChicago O'Hare Intl

May 5

ORD6:00 amChicago O'Hare Intl

9h 15m

1 stop

OAK1:15 pmOakland

$259

Alaska Airlines

May 18

OAK6:02 amOakland

15h 53m

1 stop

ORD11:55 pmChicago O'Hare Intl

May 19

ORD9:00 amChicago O'Hare Intl

11h 21m

1 stop

OAK6:21 pmOakland

$266

Alaska Airlines

Apr 27

OAK6:20 amOakland

15h 39m

1 stop

ORD11:59 pmChicago O'Hare Intl

Apr 29

ORD6:00 amChicago O'Hare Intl

9h 15m

1 stop

OAK1:15 pmOakland

$271

Delta flights from Oakland, California to Illinois

Our best Delta deals on Oakland, California to Illinois flight tickets

Delta

Mar 31

OAK12:35 pmOakland

6h 59m

1 stop

ORD9:34 pmChicago O'Hare Intl

Apr 7

ORD8:55 amChicago O'Hare Intl

9h 05m

2 stops

OAK4:00 pmOakland

$270

Delta

Apr 15

OAK12:34 pmOakland

6h 44m

1 stop

ORD9:18 pmChicago O'Hare Intl

Apr 17

ORD7:10 pmChicago O'Hare Intl

6h 44m

1 stop

OAK11:54 pmOakland

$276

Delta

Apr 15

OAK12:34 pmOakland

6h 44m

1 stop

ORD9:18 pmChicago O'Hare Intl

Apr 17

ORD7:15 amChicago O'Hare Intl

11h 09m

2 stops

OAK4:24 pmOakland

$280

momondo Fare Finder

Use the filters below to find and compare flights from Oakland, California to Illinois that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Tue 4/28

11:55 pm-6:00 am

Nonstop4h 05m

Chicago Midway

Wed 4/29

8:50 pm-11:25 pm

Nonstop4h 35m

$177

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Tue 4/28

5:50 am-11:55 am

Nonstop4h 05m

Chicago Midway

Wed 4/29

5:35 pm-10:25 pm

1 stop6h 50m

$187

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Tue 4/28

6:45 pm-4:35 am

1 stop7h 50m

Chicago Midway

Wed 4/29

5:15 pm-9:55 pm

1 stop6h 40m

$197

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Tue 4/28

11:55 pm-6:00 am

Nonstop4h 05m

Chicago Midway

Sat 5/2

5:55 pm-8:30 pm

Nonstop4h 35m

$211

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sat 5/2

2:09 pm-11:59 pm

1 stop7h 50m

Chicago O'Hare Intl

Tue 5/5

6:00 am-1:15 pm

1 stop9h 15m

$259

OaklandChicago

OAK - ORD

OAKORD

Oakland

Mon 5/18

6:02 am-11:55 pm

1 stop15h 53m

Chicago O'Hare Intl

Tue 5/19

9:00 am-6:21 pm

1 stop11h 21m

$266

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 3/31

12:35 pm-9:34 pm

1 stop6h 59m

Chicago O'Hare Intl

Tue 4/7

8:55 am-4:00 pm

2 stops9h 05m

$270

OaklandChicago

OAK - ORD

OAKORD

Oakland

Mon 4/27

6:20 am-11:59 pm

1 stop15h 39m

Chicago O'Hare Intl

Wed 4/29

6:00 am-1:15 pm

1 stop9h 15m

$271

OaklandSt. Louis

OAK - STL

OAKSTL

Oakland

Mon 4/6

4:49 pm-12:21 am

1 stop5h 32m

Lambert-St Louis

Tue 4/7

7:15 am-11:51 am

1 stop6h 36m

$362

OaklandEvansville

OAK - EVV

OAKEVV

Oakland

Sat 7/25

5:05 pm-9:26 am

2 stops14h 21m

Evansville Dress Regional

Mon 7/27

1:30 pm-11:49 pm

2 stops12h 19m

$888

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Oakland, California to Illinois

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the cheapest month to fly to Illinois?

The cheapest month to fly to Illinois from Oakland, California is in July. Flight prices, which tend to average around $302, are often lower during this time because this is during the off-season. If you aren’t able to travel to Illinois during the month of July, then flying in February is also cheap. Prices for this month can be found on momondo for an average of $331.

What is the cheapest day to depart on your flight to Illinois?

The cheapest day to depart from Oakland, California to Illinois is on a Monday when prices can be found for as low as $433. Flights from Oakland, California to Illinois on a Saturday will generally be more expensive and average around $486. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Illinois?

Our most recent data shows that the best time of day to fly to Illinois is in the afternoon. Flights from Oakland, California to Illinois during this time can be as low as $363. Flights at noon are often more expensive with an average ticket price of $791.

What is the cheapest Oakland to Illinois flight route?

Fly from Oakland to Chicago Midway for the best Oakland - Illinois flight prices

What cabin class options are available on Oakland to Illinois flights?

There is only 1 cabin class available to choose from on Oakland to Illinois flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Oakland, California to Illinois flights?

You could potentially save up to 12% on your flight if you consider stops on a Oakland, California to Illinois flight.

Cheap Oakland, California to Illinois flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Oakland, California to Illinois

Best Price Found	$199
Fastest flight time	4h 00m
Direct flights	Every day
Airports in Illinois	98 airports

The best one-way flight to Illinois from Oakland, California in the past 72 hours is $199. The best round-trip flight deal from Oakland, California to Illinois found on momondo in the last 72 hours is $340.

The fastest flight from Oakland, California to Illinois takes 4h 00m

Direct flights go from Oakland, California to Illinois every day.

There are 98 airports in Illinois. From Oakland, California there are direct flights to Chicago Midway (MDW).

Search flight deals

When did momondo last update prices for flights from Oakland Airport to Illinois?
Prices for flights from Oakland Airport to Illinois were last updated today.
How many operators does momondo search for flights from Oakland Airport to Illinois?
The number of operators available for flights from Oakland Airport to Illinois is 5 as of March 2026.
How old do you have to be to fly from Oakland Airport to Illinois?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Oakland Airport to Illinois.
What documentation or ID do you need to fly to Illinois?
The necessary travel and health documents for your Illinois trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Oakland, California to Illinois?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Oakland, California to Illinois is Boeing 737 MAX 8 (23.62% of total bookings). The next most popular plane models are Boeing 737-800 Passenger/BBJ2 (winglets) (15.08%), Airbus A321neo (10.05%), and Boeing 737 MAX 9 (6.03%).

Best airlines flying from Oakland, California to Illinois

Compare and see reviews for airlines that fly from Oakland, California to Illinois with momondo

Airline	Rating	Free Cancellation	Price
Spirit Airlines	PriceFrom $108	Free Cancellation	Rating 6.3 8,486 reviews	Search Spirit Airlines flights
United Airlines	PriceFrom $163	Free Cancellation	Rating 7.4 9,375 reviews	Search United Airlines flights
Alaska Airlines	PriceFrom $237	Free Cancellation	Rating 8.0 11,977 reviews	Search Alaska Airlines flights
Southwest	PriceFrom $246	Free Cancellation	Rating 8.0 4,307 reviews	Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Oakland to Illinois?

Finding the right flight to Illinois from Oakland is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Illinois quick and easy, saving you time and money.

Can I find flights from Oakland to Illinois with flexible booking policies on momondo?

Flights from Oakland to Illinois with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Oakland to Illinois?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Oakland to Illinois.

I’m not ready to book a flight from Oakland to Illinois right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Illinois from Oakland. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.