How often are flights from Chicago to Oakland delayed?

Historically, on average around 23% 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 96 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 49% 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.

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

As of February 2026, 8 flights take off from Chicago and land in Oakland, California each week. The most common flight departure day for this route is Fri, with 25% of weekly flights taking off on this day.

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

Flights via Salt Lake City (SLC) offer the lowest average round-trip price of $311.

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 27% 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.

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

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

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

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

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.

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 day?

1 flights are operational daily from Chicago to Oakland, California as of February 2026. The most popular departure time for this route is 11:00AM, with 80% of flights per day taking off at noon.

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

Salt Lake City (SLC) has the shortest average layover time for this route: 1h 39m.

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 February 2026, 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.

$109 Cheap Flights from Chicago to Oakland in 2026

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 $295 to $429. The lowest price recently found on this route was $217.

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Round-trip

One-way

Last minute

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Cheap round-trip flights

Enter your travel dates to find the best prices.

8:55 pm - 11:50 pm

MDW

OAK

4h 55mnonstop

5:40 am - 11:40 am

OAK

MDW

4h 00mnonstop

$217Southwest

сб., фев 28 - сб., мар 7

3:52 pm - 6:15 pm

ORD

OAK

28h 23m

1 stop

3:18 pm - 11:43 pm

OAK

ORD

6h 25m

1 stop

$220Alaska Airlines

пт., апр 24 - пн., апр 27

3:55 pm - 8:20 pm

MDW

OAK

6h 25m

1 stop

11:55 pm - 6:00 am

OAK

MDW

4h 05mnonstop

$223Southwest

ср., апр 22 - сб., апр 25

7:59 pm - 10:17 am

ORD

OAK

16h 18m

1 stop

3:18 pm - 11:43 pm

OAK

ORD

6h 25m

1 stop

$223Alaska Airlines

пт., апр 24 - пн., апр 27

8:55 pm - 11:50 pm

MDW

OAK

4h 55mnonstop

3:30 pm - 1:55 am

OAK

MDW

8h 25m

1 stop

$227Southwest

сб., фев 28 - сб., мар 7

3:55 pm - 8:20 pm

MDW

OAK

6h 25m

1 stop

7:50 pm - 5:00 am

OAK

MDW

7h 10m

1 stop

$232Southwest

ср., апр 22 - сб., апр 25

3:54 pm - 10:49 pm

ORD

OAK

8h 55m

1 stop

6:15 am - 4:33 pm

OAK

ORD

8h 18m

1 stop

$237Alaska Airlines

ср., фев 25 - сб., фев 28

6:45 pm - 11:51 pm

ORD

OAK

7h 06m

1 stop

4:49 pm - 8:30 am

OAK

ORD

13h 41m

2 stops

$242Delta

вс., мар 1 - пн., мар 9

2:05 pm - 11:51 pm

ORD

OAK

11h 46m

2 stops

5:55 am - 4:41 pm

OAK

ORD

8h 46m

2 stops

$247Delta

вт., фев 24 - вт., мар 3

1:49 pm - 11:51 pm

MDW

OAK

12h 02m

2 stops

5:55 am - 5:37 pm

OAK

MDW

9h 42m

2 stops

$247Delta

вт., фев 24 - вт., мар 3

Alaska Airlines flights from Chicago to Oakland, California

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

Alaska Airlines

Apr 24

ORD7:59 pmChicago O'Hare Intl

16h 18m

1 stop

OAK10:17 amOakland

Apr 27

OAK3:18 pmOakland

6h 25m

1 stop

ORD11:43 pmChicago O'Hare Intl

$223

Alaska Airlines

Feb 25

ORD3:54 pmChicago O'Hare Intl

8h 55m

1 stop

OAK10:49 pmOakland

Feb 28

OAK6:15 amOakland

8h 18m

1 stop

ORD4:33 pmChicago O'Hare Intl

$237

Alaska Airlines

Apr 18

ORD6:00 amChicago O'Hare Intl

13h 46m

1 stop

OAK5:46 pmOakland

Apr 28

OAK10:57 amOakland

24h 16m

1 stop

ORD1:13 pmChicago O'Hare Intl

$250

Delta flights from Chicago to Oakland, California

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

Delta

Mar 1

ORD6:45 pmChicago O'Hare Intl

7h 06m

1 stop

OAK11:51 pmOakland

Mar 9

OAK4:49 pmOakland

13h 41m

2 stops

ORD8:30 amChicago O'Hare Intl

$242

Delta

Feb 24

ORD2:05 pmChicago O'Hare Intl

11h 46m

2 stops

OAK11:51 pmOakland

Mar 3

OAK5:55 amOakland

8h 46m

2 stops

ORD4:41 pmChicago O'Hare Intl

$247

Delta

Mar 3

ORD6:45 pmChicago O'Hare Intl

7h 06m

1 stop

OAK11:51 pmOakland

Mar 7

OAK12:40 pmOakland

7h 12m

1 stop

ORD9:52 pmChicago O'Hare Intl

$268

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

сб. 2/28

8:55 pm-11:50 pm

Nonstop4h 55m

Oakland

сб. 3/7

5:40 am-11:40 am

Nonstop4h 00m

$217

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

пт. 4/24

3:52 pm-6:15 pm

1 stop28h 23m

Oakland

пн. 4/27

3:18 pm-11:43 pm

1 stop6h 25m

$220

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

ср. 4/22

3:55 pm-8:20 pm

1 stop6h 25m

Oakland

сб. 4/25

11:55 pm-6:00 am

Nonstop4h 05m

$223

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

пт. 4/24

7:59 pm-10:17 am

1 stop16h 18m

Oakland

пн. 4/27

3:18 pm-11:43 pm

1 stop6h 25m

$223

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

сб. 2/28

8:55 pm-11:50 pm

Nonstop4h 55m

Oakland

сб. 3/7

3:30 pm-1:55 am

1 stop8h 25m

$227

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

ср. 4/22

3:55 pm-8:20 pm

1 stop6h 25m

Oakland

сб. 4/25

7:50 pm-5:00 am

1 stop7h 10m

$232

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

ср. 2/25

3:54 pm-10:49 pm

1 stop8h 55m

Oakland

сб. 2/28

6:15 am-4:33 pm

1 stop8h 18m

$237

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

вс. 3/1

6:45 pm-11:51 pm

1 stop7h 06m

Oakland

пн. 3/9

4:49 pm-8:30 am

2 stops13h 41m

$242

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

вт. 2/24

2:05 pm-11:51 pm

2 stops11h 46m

Oakland

вт. 3/3

5:55 am-4:41 pm

2 stops8h 46m

$247

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

вт. 2/24

1:49 pm-11:51 pm

2 stops12h 02m

Oakland

вт. 3/3

5:55 am-5:37 pm

2 stops9h 42m

$247

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 $337. 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 $615.

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 $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 15% 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 February 2026, prices for Chicago to Oakland, California flights are approximately 9% 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	$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 Chicago in the past 72 hours is $323. The best round-trip flight deal from Chicago to Oakland, California found on momondo in the last 72 hours is $289.

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 in Oakland, California. From Chicago there are direct flights to 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 30m.
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 February 2026, 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 22.37% of all bookings. The subsequent popular models are Boeing 787-10 Dreamliner at 10.53%, Airbus A321neo at 10.53%, and Boeing 787-8 Dreamliner at 7.89%.
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 10%, United Airlines at 8%, and Delta 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 $53	Free Cancellation	Rating 6.3 8,390 reviews		Search Spirit Airlines flights
Southwest	PriceFrom $236	Free Cancellation	Rating 8.0 4,268 reviews		Search Southwest flights

Southwest Flights From Chicago to Oakland, California
Southwest flies from Chicago to Oakland, California around 8 times per week, with 4,268 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 $414 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.

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Cheap flights from Chicago to San Francisco from $109

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 3/14. 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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Alaska Airlines flights from Chicago to Oakland, California

Our best Alaska Airlines 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

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

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 15% 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 February 2026, prices for Chicago to Oakland, California flights are approximately 9% 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 23% 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 96 minutes.

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

Generally, flights departing in the early afternoon 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?

Friday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday 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 27% 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 Salt Lake City (SLC) offer the lowest average round-trip price of $311.

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?

Salt Lake City (SLC) has the shortest average layover time for this route: 1h 39m.

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

1 flights are operational daily from Chicago to Oakland, California as of February 2026. The most popular departure time for this route is 11:00AM, with 80% of flights per day taking off at noon.

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

As of February 2026, 8 flights take off from Chicago and land in Oakland, California each week. The most common flight departure day for this route is Fri, with 25% 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?