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 week?

23 flights are operational weekly from Illinois to Oakland, California as of March 2026. The most popular departure day for this route is Mon, with 22% of flights per week taking off on this day.

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

As of March 2026, 3 flights take off from Illinois and land in Oakland, California each day. The most common flight departure time for this route is 10:00AM, with 50% of daily flights taking off at noon.

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 32m and 6h 41m, 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 49% of people opting to fly with this airline when traveling to Oakland, California. Keep in mind that there are 9 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 March 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.

$104 Cheap Flights from Illinois to Oakland in 2026

1 adult

0 bags

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Illinois to San Francisco

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

9:50 pm - 12:25 am

MDW

OAK

4h 35mnonstop

11:55 pm - 6:00 am

OAK

MDW

4h 05mnonstop

$207Southwest

Thu, Apr 16 - Sat, Apr 25

3:55 pm - 8:20 pm

MDW

OAK

6h 25m

1 stop

11:55 pm - 6:00 am

OAK

MDW

4h 05mnonstop

$213Southwest

Tue, Apr 21 - Tue, Apr 28

4:30 pm - 8:45 pm

MDW

OAK

6h 15m

1 stop

11:55 pm - 6:00 am

OAK

MDW

4h 05mnonstop

$217Southwest

Tue, Apr 14 - Tue, Apr 21

3:55 pm - 8:20 pm

MDW

OAK

6h 25m

1 stop

7:55 pm - 5:20 am

OAK

MDW

7h 25m

1 stop

$222Southwest

Wed, May 6 - Sat, Jun 6

6:00 am - 4:24 pm

MDW

OAK

12h 24m

2 stops

5:55 am - 6:36 pm

OAK

MDW

10h 41m

2 stops

$237Delta

Wed, Apr 15 - Sat, Apr 18

7:59 pm - 10:17 am

ORD

OAK

16h 18m

1 stop

6:55 pm - 1:13 pm

OAK

ORD

16h 18m

1 stop

$257Alaska Airlines

Fri, Apr 24 - Mon, Apr 27

5:00 pm - 10:34 pm

ORD

OAK

7h 34m

1 stop

12:28 pm - 9:50 pm

OAK

ORD

7h 22m

1 stop

$259Delta

Sat, May 30 - Mon, Jun 1

5:19 pm - 11:57 pm

ORD

OAK

8h 38m

2 stops

12:28 pm - 9:50 pm

OAK

ORD

7h 22m

1 stop

$264Delta

Thu, Jun 4 - Sat, Jun 6

3:52 pm - 10:23 pm

ORD

OAK

8h 31m

1 stop

8:10 pm - 5:05 am

OAK

ORD

6h 55m

1 stop

$272Alaska Airlines

Thu, May 7 - Tue, May 12

4:46 pm - 10:32 pm

STL

OAK

7h 46m

1 stop

7:00 am - 6:45 pm

OAK

STL

9h 45m

1 stop

$337Alaska Airlines

Tue, May 12 - Tue, May 19

Southwest flights from Illinois to Oakland, California

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

Southwest

Apr 21

MDW8:50 pmChicago Midway

4h 35m

OAK11:25 pmOakland

Apr 28

OAK11:55 pmOakland

4h 05m

MDW6:00 amChicago Midway

$207

Southwest

Apr 21

MDW3:55 pmChicago Midway

6h 25m

1 stop

OAK8:20 pmOakland

Apr 28

OAK11:55 pmOakland

4h 05m

MDW6:00 amChicago Midway

$213

Southwest

Apr 14

MDW4:30 pmChicago Midway

6h 15m

1 stop

OAK8:45 pmOakland

Apr 21

OAK11:55 pmOakland

4h 05m

MDW6:00 amChicago Midway

$217

Alaska Airlines flights from Illinois to Oakland, California

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

Alaska Airlines

Apr 24

ORD7:59 pmChicago O'Hare Intl

16h 18m

1 stop

OAK10:17 amOakland

Apr 27

OAK6:55 pmOakland

16h 18m

1 stop

ORD1:13 pmChicago O'Hare Intl

$257

Alaska Airlines

May 7

ORD3:52 pmChicago O'Hare Intl

8h 31m

1 stop

OAK10:23 pmOakland

May 12

OAK8:10 pmOakland

6h 55m

1 stop

ORD5:05 amChicago O'Hare Intl

$272

Alaska Airlines

May 28

ORD2:10 pmChicago O'Hare Intl

11h 40m

1 stop

OAK11:50 pmOakland

Jun 1

OAK8:13 pmOakland

15h 01m

1 stop

ORD1:14 pmChicago O'Hare Intl

$285

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

Cheapest round-trip

Quickest round-trip

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Thu 4/16

9:50 pm-12:25 am

Nonstop4h 35m

Oakland

Sat 4/25

11:55 pm-6:00 am

Nonstop4h 05m

$207

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Tue 4/21

3:55 pm-8:20 pm

1 stop6h 25m

Oakland

Tue 4/28

11:55 pm-6:00 am

Nonstop4h 05m

$213

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Tue 4/14

4:30 pm-8:45 pm

1 stop6h 15m

Oakland

Tue 4/21

11:55 pm-6:00 am

Nonstop4h 05m

$217

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Wed 5/6

3:55 pm-8:20 pm

1 stop6h 25m

Oakland

Sat 6/6

7:55 pm-5:20 am

1 stop7h 25m

$222

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Wed 4/15

6:00 am-4:24 pm

2 stops12h 24m

Oakland

Sat 4/18

5:55 am-6:36 pm

2 stops10h 41m

$237

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Fri 4/24

7:59 pm-10:17 am

1 stop16h 18m

Oakland

Mon 4/27

6:55 pm-1:13 pm

1 stop16h 18m

$257

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Sat 5/30

5:00 pm-10:34 pm

1 stop7h 34m

Oakland

Mon 6/1

12:28 pm-9:50 pm

1 stop7h 22m

$259

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Thu 6/4

5:19 pm-11:57 pm

2 stops8h 38m

Oakland

Sat 6/6

12:28 pm-9:50 pm

1 stop7h 22m

$264

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Thu 5/7

3:52 pm-10:23 pm

1 stop8h 31m

Oakland

Tue 5/12

8:10 pm-5:05 am

1 stop6h 55m

$272

St. LouisOakland

STL - OAK

STLOAK

Lambert-St Louis

Tue 5/12

4:46 pm-10:32 pm

1 stop7h 46m

Oakland

Tue 5/19

7:00 am-6:45 pm

1 stop9h 45m

$337

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 $376. 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 $643.

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 $287. 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 $611.

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?

No. A direct flight is the cheapest option for a flight between Illinois 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	$126
Fastest flight time	4h 25m
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 $126. The best round-trip flight deal from Illinois to Oakland, California found on momondo in the last 72 hours is $365.

The fastest flight from Illinois to Oakland, California takes 4h 25m

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 March 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 32.20% of the total bookings. Other popular models include Airbus A321neo with 11.02%, Boeing 737-800 with 9.32%, and Boeing 757-300 with 8.47%.

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 8,564 reviews		Search Spirit Airlines flights
Southwest	PriceFrom $236	Free Cancellation	Rating 8.0 4,329 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

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.

Start using Trips

Find my bookings

Get notified when prices go down

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

1 adult

Wed 4/29

Wed 5/6

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

Nearby airports

Airlines

Cabin classes

Other United States destinations

Other flights from Illinois

Complete your trip

Feeling lucky

Cheap flights from Illinois to San Francisco from $104

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 4/23. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Illinois to San Francisco

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Southwest flights from Illinois to Oakland, California

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

Alaska Airlines flights from Illinois to Oakland, California

Our best Alaska Airlines 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?

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.

Popular cities in the United States

Popular flights according to clicks in the last 7 days on momondo

Fly to other destinations from Illinois

According to popular flight searches on momondo this year

Complete your trip to San Francisco

Explore popular destinations other users love

According to popular flight searches on momondo this year