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 day of the week experiences the fewest flight delays on this route?

Wednesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Monday has historically seen more delays on average compared to the rest of the week.

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

Las Vegas (LAS) was the most common stop: 50% of momondo users choosing 1-stop flights on this route connected there.

Which airline has the best punctuality record on Chicago to Oakland flights?

According to our data, Southwest have had the least number of delays on this route over the last 12 months; with about 24% of their flights experiencing any sort of delay.

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

Southwest, Alaska Airlines, and Delta 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 December 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.

What is the most punctual flight time for Chicago to Oakland flights?

Generally, flights departing in the morning tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

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.

How often are flights from Chicago to Oakland delayed?

Historically, on average around 22% of flights between Chicago and Oakland have experienced a delay on any given week. The average delay length over the past 12 months has been 98 minutes.

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 December 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.

$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.

11:10 am - 2:05 pmMDW-OAK

4h 55mnonstop

11:10 am - 5:15 pmOAK-MDW

4h 05mnonstop

$123Southwest

Find Deal

Wed, Jan 21 - Wed, Jan 28

8:10 am - 2:55 pmMDW-OAK

8h 45m1 stop

11:10 am - 5:15 pmOAK-MDW

4h 05mnonstop

$133Southwest

Find Deal

Wed, Jan 21 - Wed, Jan 28

8:10 am - 2:55 pmMDW-OAK

8h 45m2 stops

11:10 am - 5:15 pmOAK-MDW

4h 05mnonstop

$138Southwest

Find Deal

Wed, Jan 21 - Wed, Jan 28

1:00 pm - 6:40 pmORD-OAK

7h 40m1 stop

12:30 pm - 10:35 pmOAK-ORD

8h 05m1 stop

$143Southwest

Find Deal

Wed, Jan 21 - Wed, Jan 28

4:10 pm - 9:45 pmMDW-OAK

7h 35m1 stop

8:30 pm - 5:05 amOAK-MDW

6h 35m1 stop

$143Southwest

Find Deal

Wed, Jan 7 - Wed, Jan 14

4:25 pm - 9:45 pmORD-OAK

7h 20m1 stop

11:50 am - 10:35 pmOAK-ORD

8h 45m2 stops

$148Southwest

Find Deal

Wed, Jan 21 - Wed, Jan 28

2:10 pm - 7:50 pmMDW-OAK

7h 40m1 stop

7:20 am - 6:45 pmOAK-MDW

9h 25m2 stops

$148Southwest

Find Deal

Wed, Jan 7 - Wed, Jan 14

2:10 pm - 7:50 pmMDW-OAK

7h 40m1 stop

11:10 am - 5:15 pmOAK-MDW

4h 05mnonstop

$149Southwest

Find Deal

Wed, Jan 7 - Wed, Jan 14

8:00 am - 10:28 amORD-OAK

28h 28m1 stop

5:17 pm - 2:38 pmOAK-ORD

19h 21m1 stop

$154Alaska Airlines

Find Deal

Tue, Jan 20 - Mon, Jan 26

8:00 am - 4:23 pmORD-OAK

10h 23m1 stop

11:43 am - 11:50 pmOAK-ORD

10h 07m1 stop

$158Alaska Airlines

Find Deal

Mon, Jan 12 - Tue, Jan 20

Southwest flights from Chicago to Oakland, California

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

Southwest

Jan 21

MDW11:10 amChicago Midway

4h 55m

OAK2:05 pmOakland

Jan 28

OAK11:10 amOakland

4h 05m

MDW5:15 pmChicago Midway

$123

Find similar

Southwest

Jan 21

MDW8:10 amChicago Midway

8h 45m

1 stop

OAK2:55 pmOakland

Jan 28

OAK11:10 amOakland

4h 05m

MDW5:15 pmChicago Midway

$133

Find similar

Southwest

Jan 21

MDW8:10 amChicago Midway

8h 45m

2 stops

OAK2:55 pmOakland

Jan 28

OAK11:10 amOakland

4h 05m

MDW5:15 pmChicago Midway

$138

Find similar

Delta flights from Chicago to Oakland, California

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

Delta

Dec 14

ORD7:40 pmChicago O'Hare Intl

6h 28m

1 stop

OAK12:08 amOakland

Mar 3

OAK12:37 pmOakland

21h 42m

1 stop

ORD12:19 pmChicago O'Hare Intl

$390

Find similar

Delta

Dec 14

ORD7:40 pmChicago O'Hare Intl

6h 28m

1 stop

OAK12:08 amOakland

Mar 9

OAK12:35 pmOakland

6h 59m

1 stop

ORD9:34 pmChicago O'Hare Intl

$427

Find similar

Delta

Dec 12

ORD7:40 pmChicago O'Hare Intl

6h 28m

1 stop

OAK12:08 amOakland

Dec 15

OAK5:55 amOakland

12h 00m

2 stops

ORD7:55 pmChicago O'Hare Intl

$432

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

Wed 1/21

11:10 am-2:05 pm

Nonstop4h 55m

Oakland

Wed 1/28

11:10 am-5:15 pm

Nonstop4h 05m

$123

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Wed 1/21

8:10 am-2:55 pm

1 stop8h 45m

Oakland

Wed 1/28

11:10 am-5:15 pm

Nonstop4h 05m

$133

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Wed 1/21

8:10 am-2:55 pm

2 stops8h 45m

Oakland

Wed 1/28

11:10 am-5:15 pm

Nonstop4h 05m

$138

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Wed 1/21

1:00 pm-6:40 pm

1 stop7h 40m

Oakland

Wed 1/28

12:30 pm-10:35 pm

1 stop8h 05m

$143

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Wed 1/7

4:10 pm-9:45 pm

1 stop7h 35m

Oakland

Wed 1/14

8:30 pm-5:05 am

1 stop6h 35m

$143

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Wed 1/21

4:25 pm-9:45 pm

1 stop7h 20m

Oakland

Wed 1/28

11:50 am-10:35 pm

2 stops8h 45m

$148

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Wed 1/7

2:10 pm-7:50 pm

1 stop7h 40m

Oakland

Wed 1/14

7:20 am-6:45 pm

2 stops9h 25m

$148

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Wed 1/7

2:10 pm-7:50 pm

1 stop7h 40m

Oakland

Wed 1/14

11:10 am-5:15 pm

Nonstop4h 05m

$149

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Tue 1/20

8:00 am-10:28 am

1 stop28h 28m

Oakland

Mon 1/26

5:17 pm-2:38 pm

1 stop19h 21m

$154

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Mon 1/12

8:00 am-4:23 pm

1 stop10h 23m

Oakland

Tue 1/20

11:43 am-11:50 pm

1 stop10h 07m

$158

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

Delays

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?

No. A direct flight is the cheapest option for a flight between Chicago to Oakland, California.

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

As of December 2025, prices for Chicago to Oakland, California flights are approximately 80% 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	$192
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 $192. 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 40m.
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 December 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 31.25% of all bookings. The subsequent popular models are Airbus A321neo at 8.75%, Boeing 737-800 at 7.50%, and Boeing 757-300 at 7.50%.
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 72% of all bookings. The subsequent popular airlines are Spirit Airlines at 11%, United Airlines at 7%, and Alaska Airlines at 6%.

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 8,158 reviews		Search Spirit Airlines flights
Southwest	PriceFrom $236	Free Cancellation	Rating 8.0 4,254 reviews		Search Southwest flights

Southwest Flights From Chicago to Oakland, California
Southwest flies from Chicago to Oakland, California around 5 times per week, with 4,254 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Chicago to Oakland, California in the last 72 hours was $236 (round-trip), much lower than the average airfare cost of $430 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

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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 1/6. 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.

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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

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?

No. A direct flight is the cheapest option for a flight between Chicago to Oakland, California.

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

As of December 2025, prices for Chicago to Oakland, California flights are approximately 80% more expensive when compared to flights at the same time last year.

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

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

What airlines fly to Oakland, California?

How often are flights from Chicago to Oakland delayed?

Historically, on average around 22% of flights between Chicago and Oakland have experienced a delay on any given week. The average delay length over the past 12 months has been 98 minutes.

What is the most punctual flight time for Chicago to Oakland flights?

Generally, flights departing in the morning tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

What day of the week experiences the fewest flight delays on this route?

Wednesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Monday has historically seen more delays on average compared to the rest of the week.

Which airline has the best punctuality record on Chicago to Oakland flights?

According to our data, Southwest have had the least number of delays on this route over the last 12 months; with about 24% of their flights experiencing any sort of delay.

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

Las Vegas (LAS) was the most common stop: 50% 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 December 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