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

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

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

As of February 2026, 2 flights take off from Illinois and land in Oakland, California each day. The most common flight departure time for this route is 8:00AM, with 66% of daily flights taking off at noon.

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

16 flights are operational weekly from Illinois to Oakland, California as of February 2026. The most popular departure day for this route is Mon, with 31% of flights per week taking off on this day.

How long does it take to fly to Oakland, California?

If you’re flying from a popular airport in Illinois, such as Chicago or Peoria, and flying into Oakland, California, then you can expect flight times to average 4h 36m and 6h 51m, respectively.

What airlines fly to Oakland, California?

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Oakland, California from Illinois according to our data. United Airlines is the first choice among our users, with 48% of people opting to fly with this airline when traveling to Oakland, California. Keep in mind that there are 10 different airlines that fly to Oakland, California on a routine basis, so you have a few additional options to choose from.

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

Prices for flights from Illinois to Oakland Airport refresh daily.

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

The number of operators available for flights from Illinois to Oakland Airport is 3 as of February 2026.

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

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Illinois to Oakland Airport.

What documentation or ID do you need to fly to Oakland Airport?

The travel and health documents required for your trip to Oakland Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Oakland Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$96 Cheap Flights from Illinois to Oakland in 2026

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Find the cheapest flights from Illinois to San Francisco

Round-trip

One-way

Last minute

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Cheap round-trip flights

Enter your travel dates to find the best prices.

9:40 pm - 12:20 am

MDW

OAK

4h 40mnonstop

8:00 pm - 5:40 am

OAK

MDW

7h 40m

1 stop

$201Southwest

Sat, Mar 14 - Mon, Mar 23

9:30 pm - 12:10 am

MDW

OAK

4h 40mnonstop

5:50 am - 11:55 am

OAK

MDW

4h 05mnonstop

$217Southwest

Mon, Mar 9 - Tue, Mar 17

3:52 pm - 10:23 pm

ORD

OAK

8h 31m

1 stop

3:18 pm - 11:43 pm

OAK

ORD

6h 25m

1 stop

$223Alaska Airlines

Thu, Apr 30 - Mon, May 4

9:30 pm - 12:10 am

MDW

OAK

4h 40mnonstop

8:00 pm - 5:40 am

OAK

MDW

7h 40m

1 stop

$227Southwest

Mon, Mar 9 - Mon, Mar 16

8:50 am - 2:38 pm

ORD

OAK

7h 48m

1 stop

6:46 am - 7:03 pm

OAK

ORD

10h 17m

1 stop

$233Alaska Airlines

Fri, May 1 - Tue, May 5

9:00 pm - 11:40 pm

MDW

OAK

4h 40mnonstop

5:50 am - 11:55 am

OAK

MDW

4h 05mnonstop

$234Southwest

Wed, Mar 11 - Wed, Mar 25

6:45 pm - 11:51 pm

ORD

OAK

7h 06m

1 stop

12:35 pm - 9:34 pm

OAK

ORD

6h 59m

1 stop

$237Delta

Tue, Mar 3 - Wed, Mar 11

7:10 pm - 11:46 pm

ORD

OAK

6h 36m

1 stop

5:55 am - 6:00 pm

OAK

ORD

10h 05m

2 stops

$242Delta

Tue, Mar 10 - Tue, Mar 17

3:59 pm - 11:46 pm

ORD

OAK

9h 47m

2 stops

5:55 am - 6:00 pm

OAK

ORD

10h 05m

2 stops

$247Delta

Tue, Mar 10 - Tue, Mar 17

6:00 am - 6:39 pm

ORD

OAK

14h 39m

2 stops

6:46 am - 7:03 pm

OAK

ORD

10h 17m

1 stop

$255Alaska Airlines

Wed, Apr 29 - Wed, May 6

Southwest flights from Illinois to Oakland, California

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

Southwest

Mar 14

MDW9:40 pmChicago Midway

4h 40m

OAK12:20 amOakland

Mar 23

OAK8:00 pmOakland

7h 40m

1 stop

MDW5:40 amChicago Midway

$201

Southwest

Mar 9

MDW9:30 pmChicago Midway

4h 40m

OAK12:10 amOakland

Mar 17

OAK5:50 amOakland

4h 05m

MDW11:55 amChicago Midway

$217

Southwest

Mar 9

MDW9:30 pmChicago Midway

4h 40m

OAK12:10 amOakland

Mar 16

OAK8:00 pmOakland

7h 40m

1 stop

MDW5:40 amChicago Midway

$227

Delta flights from Illinois to Oakland, California

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

Delta

Mar 3

ORD6:45 pmChicago O'Hare Intl

7h 06m

1 stop

OAK11:51 pmOakland

Mar 11

OAK12:35 pmOakland

6h 59m

1 stop

ORD9:34 pmChicago O'Hare Intl

$237

Delta

Mar 10

ORD7:10 pmChicago O'Hare Intl

6h 36m

1 stop

OAK11:46 pmOakland

Mar 17

OAK5:55 amOakland

10h 05m

2 stops

ORD6:00 pmChicago O'Hare Intl

$242

Delta

Mar 10

ORD3:59 pmChicago O'Hare Intl

9h 47m

2 stops

OAK11:46 pmOakland

Mar 17

OAK5:55 amOakland

10h 05m

2 stops

ORD6:00 pmChicago O'Hare Intl

$247

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Sat 3/14

9:40 pm-12:20 am

Nonstop4h 40m

Oakland

Mon 3/23

8:00 pm-5:40 am

1 stop7h 40m

$201

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Mon 3/9

9:30 pm-12:10 am

Nonstop4h 40m

Oakland

Tue 3/17

5:50 am-11:55 am

Nonstop4h 05m

$217

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Thu 4/30

3:52 pm-10:23 pm

1 stop8h 31m

Oakland

Mon 5/4

3:18 pm-11:43 pm

1 stop6h 25m

$223

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Mon 3/9

9:30 pm-12:10 am

Nonstop4h 40m

Oakland

Mon 3/16

8:00 pm-5:40 am

1 stop7h 40m

$227

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Fri 5/1

8:50 am-2:38 pm

1 stop7h 48m

Oakland

Tue 5/5

6:46 am-7:03 pm

1 stop10h 17m

$233

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Wed 3/11

9:00 pm-11:40 pm

Nonstop4h 40m

Oakland

Wed 3/25

5:50 am-11:55 am

Nonstop4h 05m

$234

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Tue 3/3

6:45 pm-11:51 pm

1 stop7h 06m

Oakland

Wed 3/11

12:35 pm-9:34 pm

1 stop6h 59m

$237

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Tue 3/10

7:10 pm-11:46 pm

1 stop6h 36m

Oakland

Tue 3/17

5:55 am-6:00 pm

2 stops10h 05m

$242

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Tue 3/10

3:59 pm-11:46 pm

2 stops9h 47m

Oakland

Tue 3/17

5:55 am-6:00 pm

2 stops10h 05m

$247

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Wed 4/29

6:00 am-6:39 pm

2 stops14h 39m

Oakland

Wed 5/6

6:46 am-7:03 pm

1 stop10h 17m

$255

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 Illinois to Oakland, California

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 Oakland, California?

The month of September is, on average, the cheapest month to fly to Oakland, California from Illinois, with most prices found around $252. If you aren’t able to travel to Oakland, California during the month of September, then flying in July is also cheap. Prices for this month can be found on momondo for an average of $286.

What is the cheapest day to depart on your flight to Oakland, California?

According to our data, Tuesday is the cheapest day to fly to Oakland, California from Illinois. The lowest ticket price found for a Tuesday departure recently was $307. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Illinois to Oakland, California for around $623.

What is the cheapest time of day to depart on your flight to Oakland, California?

In the evening is the cheapest time of day to fly from Illinois to Oakland, California when you can find flight prices for as low as $300. Flying to Oakland, California in the evening is an ideal time because this is during off-peak travel hours. Flights in the morning are often more expensive with an average ticket price of $594.

What is the cheapest Illinois to Oakland flight route?

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

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

There is only 1 cabin class available to choose from on Illinois to Oakland 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 Illinois to Oakland, California flights?

You could potentially save up to 19% on your flight if you consider stops on a Illinois to Oakland, California flight.

Cheap Illinois to Oakland, California flight deals and tips

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

Best Price Found	$323
Fastest flight time	4h 30m
Direct flights	Every day
Airports in Oakland, California	1 airport

The best one-way flight to Oakland, California from Illinois in the past 72 hours is $323. The best round-trip flight deal from Illinois to Oakland, California found on momondo in the last 72 hours is $282.

The fastest flight from Illinois to Oakland, California takes 4h 30m

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

There is 1 airport in Oakland, California. From Illinois there are direct flights to Oakland (OAK).

Search flight deals

When did momondo last update prices for flights from Illinois to Oakland Airport?
Prices for flights from Illinois to Oakland Airport refresh daily.
How many operators does momondo search for flights from Illinois to Oakland Airport?
The number of operators available for flights from Illinois to Oakland Airport is 3 as of February 2026.
How old do you have to be to fly from Illinois to Oakland Airport?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Illinois to Oakland Airport.
What documentation or ID do you need to fly to Oakland Airport?
The travel and health documents required for your trip to Oakland Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Oakland Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Illinois to Oakland, California?
Based on momondo bookings for flights between Illinois and Oakland, California, the leading plane model is Boeing 737 MAX 8, making up 22.83% of the total bookings. Other popular models include Airbus A321neo with 10.87%, Boeing 787-10 Dreamliner with 7.61%, and Boeing 737 MAX 9 with 7.61%.

Best airlines flying from Illinois to Oakland, California

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

Airline	Rating	Free Cancellation	Price
Spirit Airlines	PriceFrom $83	Free Cancellation	Rating 6.3 8,445 reviews		Search Spirit Airlines flights
Southwest	PriceFrom $236	Free Cancellation	Rating 8.0 4,280 reviews		Search Southwest flights

Why use momondo?

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

Finding the right flight to Oakland from Illinois 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 Oakland quick and easy, saving you time and money.

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

Yes. momondo enables you to select and highlight flights to Oakland from Illinois with this policy.

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

momondo provides multiple filters to help you find the best flight to Oakland from Illinois. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

Yes momondo offers price alerts on flights to Oakland from Illinois. 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.

An easier way to manage your Oakland, California trip

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Cheap flights from Illinois to San Francisco from $96

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Illinois to San Francisco departing on 3/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Find the cheapest flights from Illinois to San Francisco

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Southwest flights from Illinois to Oakland, California

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

Delta flights from Illinois to Oakland, California

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

momondo Fare Finder

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

See travel insights to San Francisco from

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

What is the cheapest month to fly to Oakland, California?

What is the cheapest day to depart on your flight to Oakland, California?

What is the cheapest time of day to depart on your flight to Oakland, California?

What is the cheapest Illinois to Oakland flight route?

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

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

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

What airlines fly to Oakland, California?

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

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

How long does it take to fly to Oakland, California?

Cheap Illinois to Oakland, California flight deals and tips

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

Best Price Found

Fastest flight time

Direct flights

Airports in Oakland, California

Best airlines flying from Illinois to Oakland, California

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

Why use momondo?

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

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

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

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

An easier way to manage your Oakland, California trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Airports servicing California

Fly your favorite airline to San Francisco

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to San Francisco

List of cabin classes available on flights landing in San Francisco. Availability may vary depending on flight origin and airline.

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