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

Las Vegas (LAS) was the most common stop: 86% of momondo users choosing 1-stop flights on this route connected there.

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

1 flights are operational daily from Oakland, California to Chicago as of October 2025. The most popular departure time for this route is 5:00AM, with 60% of flights per day taking off at noon.

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

Flights connecting via Denver (DEN) have the shortest average one-way travel time: 5h 55m.

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

As of October 2025, 10 flights take off from Oakland, California and land in Chicago each week. The most common flight departure day for this route is Sun, with 30% of weekly flights taking off on this day.

What airlines fly to Chicago?

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Chicago from Oakland, California according to our data. United Airlines is the first choice among our users, with 50% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 8 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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

Flights via Las Vegas (LAS) offer the lowest average round-trip price of $242.

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

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

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

Denver (DEN) has the shortest average layover time for this route: 0h 53m.

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

Prices for flights from Oakland Airport to Chicago are updated daily.

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

As of October 2025, there are 4 operators available to choose from for flights from Oakland Airport to Chicago.

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

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Oakland Airport to Chicago.

What documentation or ID do you need to fly to Chicago?

The travel and health documents required for your trip to Chicago 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 Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$117 Cheap Flights from Oakland to Chicago in 2025/26

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Find the cheapest flights from Oakland, California to Chicago

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Cheap round-trip flights

Enter your travel dates to find the best prices.

2:49 pm - 12:24 amOAK-ORD

7h 35m1 stop

8:00 am - 1:55 pmORD-OAK

7h 55m1 stop

$297Alaska Airlines

Find Deal

Thu, Oct 30 - Tue, Nov 4

7:50 am - 3:25 pmOAK-MDW

5h 35m1 stop

7:45 am - 1:00 pmMDW-OAK

7h 15m1 stop

$298Southwest

Find Deal

Tue, Dec 9 - Sun, Dec 14

9:48 am - 12:24 amOAK-ORD

12h 36m2 stops

10:00 am - 11:59 pmORD-OAK

15h 59m1 stop

$298Alaska Airlines

Find Deal

Wed, Nov 5 - Wed, Nov 12

10:25 am - 7:35 pmOAK-MDW

7h 10m1 stop

6:05 pm - 10:55 pmMDW-OAK

6h 50m1 stop

$299Southwest

Find Deal

Thu, Oct 30 - Thu, Nov 6

2:49 pm - 12:24 amOAK-ORD

7h 35m1 stop

10:00 am - 11:59 pmORD-OAK

15h 59m1 stop

$299Alaska Airlines

Find Deal

Tue, Oct 28 - Wed, Nov 19

7:59 pm - 5:01 amOAK-ORD

7h 02m1 stop

8:00 am - 10:41 amORD-OAK

28h 41m1 stop

$300Alaska Airlines

Find Deal

Sat, Nov 22 - Wed, Dec 3

5:55 am - 4:57 pmOAK-ORD

9h 02m2 stops

7:40 pm - 12:08 amORD-OAK

6h 28m1 stop

$301Delta

Find Deal

Tue, Dec 9 - Sun, Dec 14

6:30 am - 12:35 pmOAK-MDW

4h 05mnonstop

3:40 pm - 9:25 pmMDW-OAK

7h 45m1 stop

$301Southwest

Find Deal

Tue, Feb 17 - Tue, Feb 24

5:55 am - 6:18 pmOAK-MDW

10h 23m2 stops

6:00 am - 4:04 pmMDW-OAK

12h 04m2 stops

$315Delta

Find Deal

Tue, Dec 9 - Sun, Dec 14

12:30 pm - 9:43 pmOAK-ORD

7h 13m1 stop

7:20 am - 11:48 amORD-OAK

6h 28m1 stop

$317Delta

Find Deal

Wed, Nov 5 - Tue, Nov 11

Alaska Airlines flights from Oakland, California to Chicago

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

Alaska Airlines

Oct 30

OAK2:49 pmOakland

7h 35m

1 stop

ORD12:24 amChicago O'Hare Intl

Nov 4

ORD8:00 amChicago O'Hare Intl

7h 55m

1 stop

OAK1:55 pmOakland

$297

Find similar

Alaska Airlines

Nov 5

OAK9:48 amOakland

12h 36m

2 stops

ORD12:24 amChicago O'Hare Intl

Nov 12

ORD10:00 amChicago O'Hare Intl

15h 59m

1 stop

OAK11:59 pmOakland

$298

Find similar

Alaska Airlines

Oct 28

OAK2:49 pmOakland

7h 35m

1 stop

ORD12:24 amChicago O'Hare Intl

Nov 19

ORD10:00 amChicago O'Hare Intl

15h 59m

1 stop

OAK11:59 pmOakland

$299

Find similar

Delta flights from Oakland, California to Chicago

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

Delta

Dec 9

OAK5:55 amOakland

9h 02m

2 stops

ORD4:57 pmChicago O'Hare Intl

Dec 14

ORD7:40 pmChicago O'Hare Intl

6h 28m

1 stop

OAK12:08 amOakland

$301

Find similar

Delta

Dec 9

OAK5:55 amOakland

10h 23m

2 stops

MDW6:18 pmChicago Midway

Dec 14

MDW6:00 amChicago Midway

12h 04m

2 stops

OAK4:04 pmOakland

$315

Find similar

Delta

Nov 5

OAK12:30 pmOakland

7h 13m

1 stop

ORD9:43 pmChicago O'Hare Intl

Nov 11

ORD7:20 amChicago O'Hare Intl

6h 28m

1 stop

OAK11:48 amOakland

$317

Find similar

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 10/30

2:49 pm-12:24 am

1 stop7h 35m

Chicago O'Hare Intl

Tue 11/4

8:00 am-1:55 pm

1 stop7h 55m

$297

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Tue 12/9

7:50 am-3:25 pm

1 stop5h 35m

Chicago Midway

Sun 12/14

7:45 am-1:00 pm

1 stop7h 15m

$298

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 11/5

9:48 am-12:24 am

2 stops12h 36m

Chicago O'Hare Intl

Wed 11/12

10:00 am-11:59 pm

1 stop15h 59m

$298

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Thu 10/30

10:25 am-7:35 pm

1 stop7h 10m

Chicago Midway

Thu 11/6

6:05 pm-10:55 pm

1 stop6h 50m

$299

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 10/28

2:49 pm-12:24 am

1 stop7h 35m

Chicago O'Hare Intl

Wed 11/19

10:00 am-11:59 pm

1 stop15h 59m

$299

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sat 11/22

7:59 pm-5:01 am

1 stop7h 02m

Chicago O'Hare Intl

Wed 12/3

8:00 am-10:41 am

1 stop28h 41m

$300

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 12/9

5:55 am-4:57 pm

2 stops9h 02m

Chicago O'Hare Intl

Sun 12/14

7:40 pm-12:08 am

1 stop6h 28m

$301

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Tue 2/17

6:30 am-12:35 pm

Nonstop4h 05m

Chicago Midway

Tue 2/24

3:40 pm-9:25 pm

1 stop7h 45m

$301

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Tue 12/9

5:55 am-6:18 pm

2 stops10h 23m

Chicago Midway

Sun 12/14

6:00 am-4:04 pm

2 stops12h 04m

$315

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 11/5

12:30 pm-9:43 pm

1 stop7h 13m

Chicago O'Hare Intl

Tue 11/11

7:20 am-11:48 am

1 stop6h 28m

$317

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Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Oakland, California to Chicago

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 Chicago?

The month of February is, on average, the cheapest month to fly to Chicago from Oakland, California, with most prices found around $289. If you’re not able to fly to Chicago in February, then July is your next best option. Flight prices from Oakland, California to Chicago during July average around $297.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $403. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Oakland, California to Chicago for around $508.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Oakland, California to Chicago during this time can be as low as $410. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $467.

What is the cheapest Oakland to Chicago flight route?

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

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

There is only 1 cabin class available to choose from on Oakland to Chicago 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 Oakland, California to Chicago flights?

You could potentially save up to 15% on your flight if you consider stops on a Oakland, California to Chicago flight.

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

As of October 2025, prices for Oakland, California to Chicago flights are approximately 117% more expensive when compared to flights at the same time last year.

When to book flights from Oakland, California to Chicago

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

Estimated round-trip price

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

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

Best Price Found	$252
Fastest flight time	4h 00m
Direct flights	Every day
Airports in Chicago	1 airport

The best one-way flight to Chicago from Oakland, California in the past 72 hours is $252. The best round-trip flight deal from Oakland, California to Chicago found on momondo in the last 72 hours is $377.

The fastest flight from Oakland, California to Chicago takes 4h 00m

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

There is 1 airport near Chicago: Chicago Midway (MDW)

Search flight deals

How far is Oakland to Chicago by plane?
The distance between Oakland and Chicago is about 1845.3 mi. Typically, this will take 4h 05m by plane in normal conditions.
When did momondo last update prices for flights from Oakland Airport to Chicago?
Prices for flights from Oakland Airport to Chicago are updated daily.
How many operators does momondo search for flights from Oakland Airport to Chicago?
As of October 2025, there are 4 operators available to choose from for flights from Oakland Airport to Chicago.
How old do you have to be to fly from Oakland Airport to Chicago?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Oakland Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents required for your trip to Chicago 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 Chicago. 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 Oakland, California to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Oakland, California to Chicago is Boeing 737-800 Passenger/BBJ2 (winglets) (19.57% of total bookings). The next most popular plane models are Boeing 737 MAX 8 (19.02%), Airbus A321neo (7.61%), and Boeing 757-300 (7.07%).
What is the most popular airline from Oakland, California to Chicago?
Based on momondo bookings for flights between Oakland, California and Chicago, the leading airline is Southwest, making up 76% of the total bookings. Other popular airlines include Spirit Airlines with 10%, United Airlines with 5%, and Alaska Airlines with 5%.

Best airlines flying from Oakland, California to Chicago

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

Airline	Rating	Free Cancellation	Price
Spirit Airlines	PriceFrom $108	Free Cancellation	Rating 6.3 8,074 reviews	Search Spirit Airlines flights
United Airlines	PriceFrom $163	Free Cancellation	Rating 7.4 8,953 reviews	Search United Airlines flights
Alaska Airlines	PriceFrom $189	Free Cancellation	Rating 8.0 10,000 reviews	Search Alaska Airlines flights
Southwest	PriceFrom $242	Free Cancellation	Rating 8.0 4,237 reviews	Search Southwest flights

Southwest Flights From Oakland, California to Chicago
Across 10 Southwest flights from Oakland, California to Chicago this week, the average price was $417, with the best Southwest deals starting from $242 round-trip. 4,237 users have rated Southwest on momondo, with an average score of 8.0/10.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Lansing

Portage

Schererville

Valparaiso

Crown Point

Munster

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Oakland.

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

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

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Oakland.

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

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

An easier way to manage your Chicago 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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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

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Flights to Washington, D.C.from $56

Flights to Bostonfrom $62

Flights to Atlantafrom $49

Flights to Dallasfrom $63

Flights to Seattlefrom $89

Flights to Denverfrom $66

Cheap flights from Oakland, California to Chicago from $117

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Oakland, California to Chicago departing on 2/15. 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 Oakland, California to Chicago

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Alaska Airlines flights from Oakland, California to Chicago

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

Delta flights from Oakland, California to Chicago

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

momondo Fare Finder

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

See travel insights to Chicago from

How to get the cheapest flight ticket from Oakland, California to Chicago

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 Chicago?

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Oakland, California to Chicago during this time can be as low as $410. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $467.

What is the cheapest Oakland to Chicago flight route?

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

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

There is only 1 cabin class available to choose from on Oakland to Chicago 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 Oakland, California to Chicago flights?

You could potentially save up to 15% on your flight if you consider stops on a Oakland, California to Chicago flight.

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

As of October 2025, prices for Oakland, California to Chicago flights are approximately 117% more expensive when compared to flights at the same time last year.

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

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

What airlines fly to Chicago?

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

Las Vegas (LAS) was the most common stop: 86% of momondo users choosing 1-stop flights on this route connected there.

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

Flights via Las Vegas (LAS) offer the lowest average round-trip price of $242.

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

Flights connecting via Denver (DEN) have the shortest average one-way travel time: 5h 55m.

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

Denver (DEN) has the shortest average layover time for this route: 0h 53m.

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

1 flights are operational daily from Oakland, California to Chicago as of October 2025. The most popular departure time for this route is 5:00AM, with 60% of flights per day taking off at noon.

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

As of October 2025, 10 flights take off from Oakland, California and land in Chicago each week. The most common flight departure day for this route is Sun, with 30% of weekly flights taking off on this day.

When to book flights from Oakland, California to Chicago

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

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

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

How far is Oakland to Chicago by plane?

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

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

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

What documentation or ID do you need to fly to Chicago?

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

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

Best airlines flying from Oakland, California to Chicago

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

Southwest Flights From Oakland, California to Chicago

Traveling to a place near Chicago?

Why use momondo?

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

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

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

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

An easier way to manage your Chicago 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

Fly into one of these airports located in Chicago