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

As of August 2025, 13 flights take off from Oakland, California and land in Chicago each week. The most common flight departure day for this route is Mon, with 23% of weekly flights taking off on this day.

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 $247.

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

Las Vegas (LAS) was the most common stop: 88% of momondo users choosing 1-stop flights on this route connected there.

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

Seattle (SEA) has the shortest average layover time for this route: 2h 43m.

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

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

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

Flights connecting via Las Vegas (LAS) have the shortest average one-way travel time: 6h 24m.

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 August 2025. The most popular departure time for this route is 5:00AM, with 62% of flights per day taking off at noon.

What airlines fly to Chicago?

United Airlines, American Airlines and Alaska Airlines 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 49% 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.

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 August 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.

$51 Cheap Flights from Oakland, California to Chicago (OAK-CHI) in 2025

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

Prices are currently low for flights on this route. Typical prices usually range from $218 to $501. The lowest price recently found on this route was $117.

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Find the cheapest flights from Oakland, California to Chicago (OAK-CHI)

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

10:56 am - 9:32 pmOAK-ORD

8h 36m2 stops

12:46 pm - 11:32 pmORD-OAK

12h 46m1 stop

$117Spirit Airlines

Find Deal

Wed, Sep 10 - Sat, Sep 20

6:30 am - 9:32 pmOAK-ORD

13h 02m1 stop

11:15 am - 11:32 pmORD-OAK

14h 17m1 stop

$118Spirit Airlines

Find Deal

Tue, Sep 9 - Tue, Sep 16

6:30 am - 6:51 pmOAK-ORD

10h 21m1 stop

12:46 pm - 11:32 pmORD-OAK

12h 46m1 stop

$127Spirit Airlines

Find Deal

Wed, Sep 10 - Sat, Sep 20

6:30 am - 6:51 pmOAK-ORD

10h 21m1 stop

11:15 am - 11:32 pmORD-OAK

14h 17m1 stop

$128Spirit Airlines

Find Deal

Wed, Sep 10 - Tue, Sep 16

2:39 pm - 11:48 amOAK-ORD

19h 09m1 stop

9:54 pm - 1:34 pmORD-OAK

17h 40m1 stop

$165

Find Deal

Wed, Sep 24 - Fri, Oct 3

6:30 am - 6:51 pmOAK-ORD

10h 21m1 stop

1:03 pm - 10:01 amORD-OAK

22h 58m2 stops

$179

Find Deal

Wed, Sep 10 - Sun, Sep 14

8:30 am - 4:25 pmOAK-MDW

5h 55m1 stop

2:05 pm - 4:45 pmMDW-OAK

4h 40mnonstop

$246Southwest

Find Deal

Sat, Nov 1 - Sat, Nov 8

1:15 pm - 10:00 pmOAK-MDW

6h 45m1 stop

1:15 pm - 3:45 pmMDW-OAK

4h 30mnonstop

$253Southwest

Find Deal

Wed, Sep 24 - Fri, Sep 26

5:05 pm - 9:40 amOAK-MDW

14h 35m2 stops

9:20 am - 4:24 pmMDW-OAK

9h 04m2 stops

$286Delta

Find Deal

Tue, Sep 30 - Sat, Oct 4

4:51 pm - 9:40 amOAK-MDW

14h 49m2 stops

9:20 am - 4:31 pmMDW-OAK

9h 11m2 stops

$328Delta

Find Deal

Mon, Oct 27 - Sat, Nov 15

Spirit Airlines flights from Oakland, California to Chicago

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

Spirit Airlines

Sep 10

OAK10:56 amOakland

8h 36m

2 stops

ORD9:32 pmChicago O'Hare Intl

Sep 20

ORD12:46 pmChicago O'Hare Intl

12h 46m

1 stop

OAK11:32 pmOakland

$117

Find similar

Spirit Airlines

Sep 9

OAK6:30 amOakland

13h 02m

1 stop

ORD9:32 pmChicago O'Hare Intl

Sep 16

ORD11:15 amChicago O'Hare Intl

14h 17m

1 stop

OAK11:32 pmOakland

$118

Find similar

Spirit Airlines

Sep 10

OAK6:30 amOakland

10h 21m

1 stop

ORD6:51 pmChicago O'Hare Intl

Sep 20

ORD12:46 pmChicago O'Hare Intl

12h 46m

1 stop

OAK11:32 pmOakland

$127

Find similar

Delta flights from Oakland, California to Chicago

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

Delta

Aug 31

OAK12:35 pmOakland

7h 29m

1 stop

ORD10:04 pmChicago O'Hare Intl

Sep 5

ORD7:45 amChicago O'Hare Intl

6h 10m

1 stop

OAK11:55 amOakland

$277

Find similar

Delta

Sep 30

OAK5:05 pmOakland

14h 35m

2 stops

MDW9:40 amChicago Midway

Oct 4

MDW9:20 amChicago Midway

9h 04m

2 stops

OAK4:24 pmOakland

$286

Find similar

Delta

Aug 31

OAK12:35 pmOakland

7h 29m

1 stop

ORD10:04 pmChicago O'Hare Intl

Sep 6

ORD6:10 amChicago O'Hare Intl

7h 45m

2 stops

OAK11:55 amOakland

$313

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

Wed 9/10

10:56 am-9:32 pm

2 stops8h 36m

Chicago O'Hare Intl

Sat 9/20

12:46 pm-11:32 pm

1 stop12h 46m

$117

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 9/9

6:30 am-9:32 pm

1 stop13h 02m

Chicago O'Hare Intl

Tue 9/16

11:15 am-11:32 pm

1 stop14h 17m

$118

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 9/10

6:30 am-6:51 pm

1 stop10h 21m

Chicago O'Hare Intl

Sat 9/20

12:46 pm-11:32 pm

1 stop12h 46m

$127

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 9/10

6:30 am-6:51 pm

1 stop10h 21m

Chicago O'Hare Intl

Tue 9/16

11:15 am-11:32 pm

1 stop14h 17m

$128

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 9/24

2:39 pm-11:48 am

1 stop19h 09m

Chicago O'Hare Intl

Fri 10/3

9:54 pm-1:34 pm

1 stop17h 40m

$165

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 9/10

6:30 am-6:51 pm

1 stop10h 21m

Chicago O'Hare Intl

Sun 9/14

1:03 pm-10:01 am

2 stops22h 58m

$179

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Sat 11/1

8:30 am-4:25 pm

1 stop5h 55m

Chicago Midway

Sat 11/8

2:05 pm-4:45 pm

Nonstop4h 40m

$246

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Wed 9/24

1:15 pm-10:00 pm

1 stop6h 45m

Chicago Midway

Fri 9/26

1:15 pm-3:45 pm

Nonstop4h 30m

$253

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Tue 9/30

5:05 pm-9:40 am

2 stops14h 35m

Chicago Midway

Sat 10/4

9:20 am-4:24 pm

2 stops9h 04m

$286

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Mon 10/27

4:51 pm-9:40 am

2 stops14h 49m

Chicago Midway

Sat 11/15

9:20 am-4:31 pm

2 stops9h 11m

$328

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

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Oakland, California, with most prices found around $236. If you’re not able to fly to Chicago in September, then August is your next best option. Flight prices from Oakland, California to Chicago during August average around $286.

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 $404. 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 $510.

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 $417. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $477.

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 are 1 cabin classes 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 39% 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 August 2025, prices for Oakland, California to Chicago flights are approximately 28% 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	$51
Fastest flight time	4h 05m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Oakland, California in the past 72 hours is $51. The best round-trip flight deal from Oakland, California to Chicago found on momondo in the last 72 hours is $117.

The fastest flight from Oakland, California to Chicago takes 4h 05m

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

There are 3 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW), Chicago Greater Rockford (RFD)

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 August 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 MAX 8 (26.17% of total bookings). The next most popular plane models are Boeing 737-800 Passenger/BBJ2 (winglets) (12.75%), Airbus A321neo (10.74%), and Boeing 737 MAX 9 (8.05%).
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 70% of the total bookings. Other popular airlines include Spirit Airlines with 17%, Alaska Airlines with 5%, and United 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 8,038 reviews	Search Spirit Airlines flights
United Airlines	PriceFrom $163	Free Cancellation	Rating 7.4 8,925 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 4,246 reviews	Search Southwest flights

Southwest Flights From Oakland, California to Chicago
Across 13 Southwest flights from Oakland, California to Chicago this week, the average price was $405, with the best Southwest deals starting from $242 round-trip. 4,246 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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Chicago Greater Rockford Airport

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Flights to Dallasfrom $58

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Flights to Denverfrom $63

Cheap flights from Oakland, California to Chicago from $51

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 9/17. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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 (OAK-CHI)

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Spirit Airlines flights from Oakland, California to Chicago

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

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 $417. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $477.

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 are 1 cabin classes 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 39% 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 August 2025, prices for Oakland, California to Chicago flights are approximately 28% more expensive when compared to flights at the same time last year.

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

Spirit Airlines, Southwest, and Hawaiian 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: 88% 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 $247.

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

Flights connecting via Las Vegas (LAS) have the shortest average one-way travel time: 6h 24m.

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

Seattle (SEA) has the shortest average layover time for this route: 2h 43m.

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 August 2025. The most popular departure time for this route is 5:00AM, with 62% of flights per day taking off at noon.

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

As of August 2025, 13 flights take off from Oakland, California and land in Chicago each week. The most common flight departure day for this route is Mon, with 23% 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