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

2 flights are operational daily from Chicago to Oakland, California as of October 2025. The most popular departure time for this route is 7:00AM, with 57% of flights per day taking off at noon.

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 Chicago 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 9 different airlines that fly to Oakland, California on a routine basis, so you have a few additional options to choose from.

Which layover airport offers the lowest fares from Chicago to Oakland, California?

Flights via Seattle (SEA) offer the lowest average round-trip price of $270.

Which layover airport has the shortest connection time from Chicago to Oakland, California?

Seattle (SEA) has the shortest average layover time for this route: 1h 05m.

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

Southwest, Hawaiian Airlines, and Alaska Airlines are the most popular carriers operating from Chicago to Oakland

Which layover airport has the shortest travel time from Chicago to Oakland, California?

Flights connecting via Salt Lake City (SLC) have the shortest average one-way travel time: 6h 10m.

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

As of October 2025, 15 flights take off from Chicago and land in Oakland, California each week. The most common flight departure day for this route is Sun, with 33% of weekly flights taking off on this day.

Which airport is the most popular layover for flights between Chicago and Oakland, California?

Las Vegas (LAS) was the most common stop: 60% of momondo users choosing 1-stop flights on this route connected there.

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

Prices for flights from Chicago to Oakland Airport are refreshed on a daily basis.

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

As of October 2025, there are 3 operators available to choose from for flights from Chicago to Oakland Airport.

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

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 Chicago 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.

$77 Cheap Flights from Chicago to Oakland in 2025/26

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Cheap round-trip flights

Enter your travel dates to find the best prices.

3:35 pm - 11:59 pmORD-OAK

10h 24m1 stop

6:10 am - 5:12 pmOAK-ORD

9h 02m1 stop

$247Alaska Airlines

Find Deal

Wed, Dec 10 - Thu, Jan 1

3:10 pm - 8:40 pmORD-OAK

7h 30m1 stop

5:15 am - 2:05 pmOAK-ORD

6h 50m1 stop

$253Southwest

Find Deal

Fri, Oct 31 - Thu, Nov 27

3:35 pm - 11:59 pmORD-OAK

10h 24m1 stop

6:10 am - 5:12 pmOAK-ORD

9h 02m1 stop

$257Alaska Airlines

Find Deal

Wed, Dec 10 - Thu, Jan 1

12:40 pm - 7:15 pmORD-OAK

8h 35m2 stops

5:15 am - 2:05 pmOAK-ORD

6h 50m1 stop

$258Southwest

Find Deal

Fri, Oct 31 - Thu, Nov 27

4:45 pm - 10:10 pmMDW-OAK

7h 25m1 stop

3:15 pm - 12:15 amOAK-MDW

7h 00m1 stop

$272Southwest

Find Deal

Tue, Dec 23 - Sat, Dec 27

3:35 pm - 11:59 pmORD-OAK

10h 24m1 stop

6:40 am - 11:59 pmOAK-ORD

15h 19m1 stop

$274Hawaiian Airlines

Find Deal

Thu, Dec 4 - Thu, Dec 11

8:00 am - 1:55 pmORD-OAK

7h 55m1 stop

2:49 pm - 12:24 amOAK-ORD

7h 35m1 stop

$280Alaska Airlines

Find Deal

Wed, Nov 12 - Wed, Nov 19

3:25 pm - 11:59 pmORD-OAK

10h 34m1 stop

6:30 am - 9:40 pmOAK-ORD

13h 10m1 stop

$283Alaska Airlines

Find Deal

Fri, Nov 14 - Sat, Nov 15

2:12 pm - 12:03 amORD-OAK

11h 51m2 stops

5:55 am - 4:52 pmOAK-ORD

8h 57m2 stops

$311Delta

Find Deal

Fri, Nov 14 - Sat, Nov 15

7:50 am - 4:10 pmORD-OAK

10h 20m2 stops

4:50 pm - 8:39 amOAK-ORD

13h 49m2 stops

$313Delta

Find Deal

Sat, Dec 6 - Mon, Dec 8

Southwest flights from Chicago to Oakland, California

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

Southwest

Oct 31

ORD3:10 pmChicago O'Hare Intl

7h 30m

1 stop

OAK8:40 pmOakland

Nov 27

OAK5:15 amOakland

6h 50m

1 stop

ORD2:05 pmChicago O'Hare Intl

$253

Find similar

Southwest

Oct 31

ORD12:40 pmChicago O'Hare Intl

8h 35m

2 stops

OAK7:15 pmOakland

Nov 27

OAK5:15 amOakland

6h 50m

1 stop

ORD2:05 pmChicago O'Hare Intl

$258

Find similar

Southwest

Dec 23

MDW4:45 pmChicago Midway

7h 25m

1 stop

OAK10:10 pmOakland

Dec 27

OAK3:15 pmOakland

7h 00m

1 stop

MDW12:15 amChicago Midway

$272

Find similar

Delta flights from Chicago to Oakland, California

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

Delta

Nov 14

ORD2:12 pmChicago O'Hare Intl

11h 51m

2 stops

OAK12:03 amOakland

Nov 15

OAK5:55 amOakland

8h 57m

2 stops

ORD4:52 pmChicago O'Hare Intl

$311

Find similar

Delta

Dec 6

ORD7:50 amChicago O'Hare Intl

10h 20m

2 stops

OAK4:10 pmOakland

Dec 8

OAK4:50 pmOakland

13h 49m

2 stops

ORD8:39 amChicago O'Hare Intl

$313

Find similar

Delta

Nov 10

ORD7:40 pmChicago O'Hare Intl

6h 23m

1 stop

OAK12:03 amOakland

Nov 18

OAK12:28 pmOakland

6h 57m

1 stop

ORD9:25 pmChicago O'Hare Intl

$321

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momondo Fare Finder

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

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Route

Depart

Return

Price

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Wed 12/10

3:35 pm-11:59 pm

1 stop10h 24m

Oakland

Thu 1/1

6:10 am-5:12 pm

1 stop9h 02m

$247

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Fri 10/31

3:10 pm-8:40 pm

1 stop7h 30m

Oakland

Thu 11/27

5:15 am-2:05 pm

1 stop6h 50m

$253

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Wed 12/10

3:35 pm-11:59 pm

1 stop10h 24m

Oakland

Thu 1/1

6:10 am-5:12 pm

1 stop9h 02m

$257

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Fri 10/31

12:40 pm-7:15 pm

2 stops8h 35m

Oakland

Thu 11/27

5:15 am-2:05 pm

1 stop6h 50m

$258

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Tue 12/23

4:45 pm-10:10 pm

1 stop7h 25m

Oakland

Sat 12/27

3:15 pm-12:15 am

1 stop7h 00m

$272

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Thu 12/4

3:35 pm-11:59 pm

1 stop10h 24m

Oakland

Thu 12/11

6:40 am-11:59 pm

1 stop15h 19m

$274

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Wed 11/12

8:00 am-1:55 pm

1 stop7h 55m

Oakland

Wed 11/19

2:49 pm-12:24 am

1 stop7h 35m

$280

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Fri 11/14

3:25 pm-11:59 pm

1 stop10h 34m

Oakland

Sat 11/15

6:30 am-9:40 pm

1 stop13h 10m

$283

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Fri 11/14

2:12 pm-12:03 am

2 stops11h 51m

Oakland

Sat 11/15

5:55 am-4:52 pm

2 stops8h 57m

$311

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Sat 12/6

7:50 am-4:10 pm

2 stops10h 20m

Oakland

Mon 12/8

4:50 pm-8:39 am

2 stops13h 49m

$313

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How to get the cheapest flight ticket from Chicago 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

Layovers

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 Chicago, 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, Monday is the cheapest day to fly to Oakland, California from Chicago. The lowest ticket price found for a Monday departure recently was $382. 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 Tuesday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to Oakland, California for around $610.

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 Chicago to Oakland, California when you can find flight prices for as low as $302. 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 $612.

What is the cheapest Chicago to Oakland flight route?

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

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

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

How have Chicago to Oakland, California flight prices changed over time?

As of October 2025, prices for Chicago to Oakland, California flights are approximately 46% more expensive when compared to flights at the same time last year.

When to book flights from Chicago to Oakland, California

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Oakland, California according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Chicago to Oakland, California (CHI to OAK) flight deals and tips

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

Best Price Found	$306
Fastest flight time	4h 30m
Direct flights	Every day
Airports in Oakland, California	1 airport

The best one-way flight to Oakland, California from Chicago in the past 72 hours is $306. The best round-trip flight deal from Chicago to Oakland, California found on momondo in the last 72 hours is $562.

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

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

There is 1 airport near Oakland, California: Oakland (OAK)

Search flight deals

How far is Chicago to Oakland by plane?
Oakland is 1845.3 mi away from Chicago. By plane, this route typically takes 4h 35m.
When did momondo last update prices for flights from Chicago to Oakland Airport?
Prices for flights from Chicago to Oakland Airport are refreshed on a daily basis.
How many operators does momondo search for flights from Chicago to Oakland Airport?
As of October 2025, there are 3 operators available to choose from for flights from Chicago to Oakland Airport.
How old do you have to be to fly from Chicago to Oakland Airport?
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 Chicago 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 Chicago to Oakland, California?
momondo data reveals that the most frequently booked plane model on the route from Chicago to Oakland, California is Boeing 737 MAX 8, representing 34.69% of all bookings. The subsequent popular models are Boeing 737-700 Passenger/BBJ1 (winglets) at 10.20%, Airbus A321neo at 6.12%, and Boeing 737-800 Passenger/BBJ2 (winglets) at 6.12%.
What is the most popular airline from Chicago to Oakland, California?
momondo data reveals that the most frequently booked airline on the route from Chicago to Oakland, California is Southwest, representing 76% of all bookings. The subsequent popular airlines are Spirit Airlines at 14%, United Airlines at 6%, and Alaska Airlines at 5%.

Best airlines flying from Chicago to Oakland, California

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

Airline	Rating	Free Cancellation	Price
Spirit Airlines	PriceFrom $83	Free Cancellation	Rating 6.3 8,097 reviews	Search Spirit Airlines flights
United Airlines	PriceFrom $236	Free Cancellation	Rating 7.4 8,990 reviews	Search United Airlines flights
Southwest	PriceFrom $242	Free Cancellation	Rating 8.0 4,239 reviews	Search Southwest flights

Southwest Flights From Chicago to Oakland, California
Southwest flies from Chicago to Oakland, California around 15 times per week, with 4,239 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Chicago to Oakland, California in the last 72 hours was $242 (round-trip), much lower than the average airfare cost of $422 for Southwest flights on this route.

Why use momondo?

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

Finding the right flight to Oakland from Chicago 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 Chicago to Oakland with flexible booking policies on momondo?

momondo does allow users to show only those flights to Oakland from Chicago which offer a flexible booking policy as well as other useful filters and features.

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

Once you have performed a search for Chicago to Oakland flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

If you are not ready to book a flight from Chicago to Oakland now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Oakland and let you know when they 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.

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Cheap flights from Chicago to San Francisco from $77

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to San Francisco departing on 1/17. 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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Southwest flights from Chicago to Oakland, California

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

Delta flights from Chicago to Oakland, California

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

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

See travel insights to San Francisco from

How to get the cheapest flight ticket from Chicago 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

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 Chicago to Oakland flight route?

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

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

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

How have Chicago to Oakland, California flight prices changed over time?

As of October 2025, prices for Chicago to Oakland, California flights are approximately 46% more expensive when compared to flights at the same time last year.

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

Southwest, Hawaiian Airlines, and Alaska Airlines are the most popular carriers operating from Chicago to Oakland

What airlines fly to Oakland, California?

Which airport is the most popular layover for flights between Chicago and Oakland, California?

Las Vegas (LAS) was the most common stop: 60% of momondo users choosing 1-stop flights on this route connected there.

Which layover airport offers the lowest fares from Chicago to Oakland, California?

Flights via Seattle (SEA) offer the lowest average round-trip price of $270.

Which layover airport has the shortest travel time from Chicago to Oakland, California?

Flights connecting via Salt Lake City (SLC) have the shortest average one-way travel time: 6h 10m.

Which layover airport has the shortest connection time from Chicago to Oakland, California?

Seattle (SEA) has the shortest average layover time for this route: 1h 05m.

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

2 flights are operational daily from Chicago to Oakland, California as of October 2025. The most popular departure time for this route is 7:00AM, with 57% of flights per day taking off at noon.

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

As of October 2025, 15 flights take off from Chicago and land in Oakland, California each week. The most common flight departure day for this route is Sun, with 33% of weekly flights taking off on this day.

When to book flights from Chicago to Oakland, California

Cheap Chicago to Oakland, California (CHI to OAK) flight deals and tips

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

Best Price Found

Fastest flight time

Direct flights

Airports in Oakland, California

How far is Chicago to Oakland by plane?

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

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

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

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

What is the most popular plane model from Chicago to Oakland, California?

What is the most popular airline from Chicago to Oakland, California?

Best airlines flying from Chicago to Oakland, California

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

Southwest Flights From Chicago to Oakland, California

Why use momondo?

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

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

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

I’m not ready to book a flight from Chicago 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