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.

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

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

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

As of November 2025, 5 flights take off from Chicago and land in Oakland, California each week. The most common flight departure day for this route is Mon, with 20% of weekly flights taking off on this day.

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.

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 offers the lowest fares from Chicago to Oakland, California?

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

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.

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 November 2025, there are 2 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.

$111 Cheap Flights from Chicago to Oakland in 2025/26

Q: What is the typical price of a round-trip flight between Chicago and Oakland, California?

Prices are currently low for flights on this route. Typical prices usually range from $441 to $770. The lowest price recently found on this route was $249.

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 Chicago to San Francisco

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

4:05 pm - 6:40 pmMDW-OAK

4h 35mnonstop

7:55 am - 4:10 pmOAK-MDW

6h 15m1 stop

$249Southwest

Find Deal

Thu, Dec 11 - Mon, Dec 15

5:51 pm - 11:59 pmORD-OAK

8h 08m1 stop

2:31 pm - 11:59 pmOAK-ORD

7h 28m1 stop

$256Alaska Airlines

Find Deal

Wed, Dec 3 - Tue, Dec 9

2:00 pm - 11:38 pmORD-OAK

11h 38m1 stop

6:35 pm - 5:04 amOAK-ORD

8h 29m1 stop

$258Alaska Airlines

Find Deal

Sat, Feb 21 - Tue, Feb 24

7:40 pm - 12:08 amORD-OAK

6h 28m1 stop

5:55 am - 1:38 pmOAK-ORD

5h 43m1 stop

$259Delta

Find Deal

Mon, Dec 8 - Wed, Jan 7

5:25 am - 11:15 amMDW-OAK

7h 50m1 stop

12:45 pm - 10:55 pmOAK-MDW

8h 10m1 stop

$259Southwest

Find Deal

Thu, Dec 11 - Mon, Dec 15

3:05 pm - 9:40 pmORD-OAK

8h 35m2 stops

12:55 pm - 10:35 pmOAK-ORD

7h 40m1 stop

$260Southwest

Find Deal

Sat, Feb 21 - Mon, Feb 23

7:40 pm - 12:08 amORD-OAK

6h 28m1 stop

5:55 am - 4:57 pmOAK-ORD

9h 02m2 stops

$264Delta

Find Deal

Tue, Dec 2 - Sat, Dec 6

5:55 pm - 10:45 pmMDW-OAK

6h 50m1 stop

7:00 am - 4:45 pmOAK-MDW

7h 45m2 stops

$264Southwest

Find Deal

Sat, Feb 21 - Tue, Feb 24

3:05 pm - 9:40 pmORD-OAK

8h 35m2 stops

11:05 am - 10:35 pmOAK-ORD

9h 30m2 stops

$265Southwest

Find Deal

Sat, Feb 21 - Tue, Feb 24

7:50 am - 12:08 amORD-OAK

18h 18m2 stops

5:55 am - 4:57 pmOAK-ORD

9h 02m2 stops

$291Delta

Find Deal

Fri, Dec 5 - Sat, Dec 6

Southwest flights from Chicago to Oakland, California

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

Southwest

Dec 11

MDW4:05 pmChicago Midway

4h 35m

OAK6:40 pmOakland

Dec 15

OAK7:55 amOakland

6h 15m

1 stop

MDW4:10 pmChicago Midway

$249

Find similar

Southwest

Dec 11

MDW5:25 amChicago Midway

7h 50m

1 stop

OAK11:15 amOakland

Jan 5

OAK5:10 pmOakland

6h 20m

1 stop

MDW1:30 amChicago Midway

$259

Find similar

Southwest

Feb 21

ORD3:05 pmChicago O'Hare Intl

8h 35m

2 stops

OAK9:40 pmOakland

Feb 23

OAK12:55 pmOakland

7h 40m

1 stop

ORD10:35 pmChicago O'Hare Intl

$260

Find similar

Alaska Airlines flights from Chicago to Oakland, California

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

Alaska Airlines

Dec 3

ORD5:51 pmChicago O'Hare Intl

8h 08m

1 stop

OAK11:59 pmOakland

Dec 9

OAK2:31 pmOakland

7h 28m

1 stop

ORD11:59 pmChicago O'Hare Intl

$256

Find similar

Alaska Airlines

Feb 21

ORD2:00 pmChicago O'Hare Intl

11h 38m

1 stop

OAK11:38 pmOakland

Feb 24

OAK6:35 pmOakland

8h 29m

1 stop

ORD5:04 amChicago O'Hare Intl

$258

Find similar

Alaska Airlines

Dec 24

ORD6:08 pmChicago O'Hare Intl

7h 51m

1 stop

OAK11:59 pmOakland

Jan 5

OAK9:35 amOakland

24h 38m

2 stops

ORD12:13 pmChicago O'Hare Intl

$266

Find similar

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Thu 12/11

4:05 pm-6:40 pm

Nonstop4h 35m

Oakland

Mon 12/15

7:55 am-4:10 pm

1 stop6h 15m

$249

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Wed 12/3

5:51 pm-11:59 pm

1 stop8h 08m

Oakland

Tue 12/9

2:31 pm-11:59 pm

1 stop7h 28m

$256

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Sat 2/21

2:00 pm-11:38 pm

1 stop11h 38m

Oakland

Tue 2/24

6:35 pm-5:04 am

1 stop8h 29m

$258

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Mon 12/8

7:40 pm-12:08 am

1 stop6h 28m

Oakland

Wed 1/7

5:55 am-1:38 pm

1 stop5h 43m

$259

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Thu 12/11

5:25 am-11:15 am

1 stop7h 50m

Oakland

Mon 12/15

12:45 pm-10:55 pm

1 stop8h 10m

$259

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Sat 2/21

3:05 pm-9:40 pm

2 stops8h 35m

Oakland

Mon 2/23

12:55 pm-10:35 pm

1 stop7h 40m

$260

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Tue 12/2

7:40 pm-12:08 am

1 stop6h 28m

Oakland

Sat 12/6

5:55 am-4:57 pm

2 stops9h 02m

$264

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Sat 2/21

5:55 pm-10:45 pm

1 stop6h 50m

Oakland

Tue 2/24

7:00 am-4:45 pm

2 stops7h 45m

$264

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Sat 2/21

3:05 pm-9:40 pm

2 stops8h 35m

Oakland

Tue 2/24

11:05 am-10:35 pm

2 stops9h 30m

$265

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Fri 12/5

7:50 am-12:08 am

2 stops18h 18m

Oakland

Sat 12/6

5:55 am-4:57 pm

2 stops9h 02m

$291

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 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 typical price of a round-trip flight between Chicago and Oakland, California?

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 $333. 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 Chicago to Oakland, California for around $617.

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

At noon is the cheapest time of day to fly from Chicago to Oakland, California when you can find flight prices for as low as $354. Flying to Oakland, California at noon 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 $613.

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.

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

You could potentially save up to 7% on your flight if you consider stops on a Chicago to Oakland, California flight.

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

As of November 2025, prices for Chicago to Oakland, California flights are approximately 83% 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	$249
Fastest flight time	4h 35m
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 $249. The best round-trip flight deal from Chicago to Oakland, California found on momondo in the last 72 hours is $387.

The fastest flight from Chicago to Oakland, California takes 4h 35m

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 November 2025, there are 2 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 34.88% of all bookings. The subsequent popular models are Airbus A321neo at 9.30%, Boeing 737-700 Passenger/BBJ1 (winglets) at 8.14%, and Boeing 757-300 at 8.14%.
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 75% of all bookings. The subsequent popular airlines are Spirit Airlines at 13%, 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 8,132 reviews		Search Spirit Airlines flights
Southwest	PriceFrom $245	Free Cancellation	Rating 8.0 4,236 reviews		Search Southwest flights

Southwest Flights From Chicago to Oakland, California
Southwest flies from Chicago to Oakland, California around 5 times per week, with 4,236 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Chicago to Oakland, California in the last 72 hours was $245 (round-trip), much lower than the average airfare cost of $441 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.

Start using Trips

Find my bookings

Get notified when prices go down

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

1 adult

Tue 12/9

Tue 12/16

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

Airports servicing California

Popular cities in the United States

Flights to New Yorkfrom $44

Flights to Los Angelesfrom $49

Flights to Miamifrom $48

Flights to Chicagofrom $54

Flights to Orlandofrom $47

Flights to Las Vegasfrom $42

Flights to San Franciscofrom $57

Flights to Washington, D.C.from $49

Flights to Bostonfrom $48

Flights to Atlantafrom $40

Flights to Dallasfrom $59

Flights to Seattlefrom $58

Fly to other destinations from Chicago

Flights from Chicago Midway to Newark

Flights from Chicago O'Hare Intl to New York John F Kennedy Intl

Flights from Chicago O'Hare Intl to Minneapolis St Paul

Flights from Chicago O'Hare Intl to Nashville Intl

Flights from Chicago Midway to Asheville Regional

Flights from Chicago Midway to Atlanta Hartsfield-Jackson

Cheap flights from Chicago to San Francisco from $111

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 2/8. 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 Chicago to San Francisco

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Southwest flights from Chicago to Oakland, California

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

Alaska Airlines flights from Chicago to Oakland, California

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

momondo Fare Finder

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 typical price of a round-trip flight between Chicago and 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 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.

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

You could potentially save up to 7% on your flight if you consider stops on a Chicago to Oakland, California flight.

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

As of November 2025, prices for Chicago to Oakland, California flights are approximately 83% more expensive when compared to flights at the same time last year.

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

Hawaiian Airlines, Southwest, 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 week?

As of November 2025, 5 flights take off from Chicago and land in Oakland, California each week. The most common flight departure day for this route is Mon, with 20% 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