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 $236.

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

Las Vegas (LAS) was the most common stop: 78% of momondo users choosing 1-stop flights on this route connected there.

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 48% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 9 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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

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

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 May 2026. The most popular departure time for this route is 11:00PM, with 70% of flights per day taking off in the evening.

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

As of May 2026, 12 flights take off from Oakland, California and land in Chicago each week. The most common flight departure day for this route is Mon, with 17% of weekly flights taking off on this day.

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 May 2026, 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.

$119 Cheap Flights from Oakland, California to Chicago in 2026

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 $495 to $341. The lowest price recently found on this route was $310.

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Find the cheapest flights from Oakland, California to Chicago

Round-trip

One-way

Last minute

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Cheap round-trip flights

Enter your travel dates to find the best prices.

8:30 pm - 4:35 am

OAK

MDW

6h 05m

1 stop

9:50 pm - 12:25 am

MDW

OAK

4h 35mnonstop

$310Southwest

Thu, May 28 - Mon, Jun 1

12:28 pm - 9:50 pm

OAK

ORD

7h 22m

1 stop

3:47 pm - 11:57 pm

ORD

OAK

10h 10m

2 stops

$311Delta

Wed, May 27 - Mon, Jun 1

2:58 pm - 11:55 pm

OAK

ORD

6h 57m

1 stop

9:00 am - 2:14 pm

ORD

OAK

7h 14m

1 stop

$313Alaska Airlines

Sat, May 23 - Wed, May 27

1:25 pm - 10:40 pm

OAK

MDW

7h 15m

1 stop

5:30 am - 9:45 am

MDW

OAK

6h 15m

1 stop

$315Southwest

Fri, May 29 - Tue, Jun 9

12:28 pm - 9:50 pm

OAK

ORD

7h 22m

1 stop

7:37 pm - 11:54 pm

ORD

OAK

6h 17m

1 stop

$315Delta

Fri, May 29 - Tue, Jun 9

9:05 pm - 5:00 am

OAK

MDW

5h 55m

1 stop

6:55 am - 12:10 pm

MDW

OAK

7h 15m

1 stop

$316Southwest

Wed, May 27 - Mon, Jun 1

1:50 pm - 10:55 pm

OAK

ORD

7h 05m

1 stop

4:50 pm - 11:55 pm

ORD

OAK

9h 05m

1 stop

$316Southwest

Wed, May 27 - Mon, Jun 1

6:00 am - 8:14 pm

OAK

ORD

12h 14m

2 stops

2:07 pm - 11:54 pm

ORD

OAK

11h 47m

2 stops

$318Delta

Tue, Jun 2 - Tue, Jun 9

11:55 pm - 6:00 am

OAK

MDW

4h 05mnonstop

6:10 pm - 10:45 pm

MDW

OAK

6h 35m

1 stop

$319Southwest

Fri, May 29 - Mon, Jun 1

8:13 pm - 6:50 pm

OAK

ORD

20h 37m

1 stop

7:59 pm - 9:45 am

ORD

OAK

15h 46m

1 stop

$329Alaska Airlines

Fri, Jun 5 - Mon, Jun 8

Alaska Airlines flights from Oakland, California to Chicago

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

Alaska Airlines

May 23

OAK2:58 pmOakland

6h 57m

1 stop

ORD11:55 pmChicago O'Hare Intl

Jun 2

ORD9:00 amChicago O'Hare Intl

7h 14m

1 stop

OAK2:14 pmOakland

$313

Alaska Airlines

Jun 3

OAK6:02 amOakland

10h 48m

1 stop

ORD6:50 pmChicago O'Hare Intl

Jun 10

ORD6:20 amChicago O'Hare Intl

9h 50m

1 stop

OAK2:10 pmOakland

$326

Alaska Airlines

Jun 5

OAK8:13 pmOakland

20h 37m

1 stop

ORD6:50 pmChicago O'Hare Intl

Jun 8

ORD7:59 pmChicago O'Hare Intl

15h 46m

1 stop

OAK9:45 amOakland

$329

Delta flights from Oakland, California to Chicago

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

Delta

May 27

OAK12:28 pmOakland

7h 22m

1 stop

ORD9:50 pmChicago O'Hare Intl

Jun 1

ORD3:47 pmChicago O'Hare Intl

10h 10m

2 stops

OAK11:57 pmOakland

$311

Delta

May 29

OAK12:28 pmOakland

7h 22m

1 stop

ORD9:50 pmChicago O'Hare Intl

Jun 9

ORD7:37 pmChicago O'Hare Intl

6h 17m

1 stop

OAK11:54 pmOakland

$315

Delta

Jun 2

OAK6:00 amOakland

12h 14m

2 stops

ORD8:14 pmChicago O'Hare Intl

Jun 9

ORD2:07 pmChicago O'Hare Intl

11h 47m

2 stops

OAK11:54 pmOakland

$318

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

Cheapest round-trip

Quickest round-trip

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Thu 5/28

8:30 pm-4:35 am

1 stop6h 05m

Chicago Midway

Mon 6/1

9:50 pm-12:25 am

Nonstop4h 35m

$310

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 5/27

12:28 pm-9:50 pm

1 stop7h 22m

Chicago O'Hare Intl

Mon 6/1

3:47 pm-11:57 pm

2 stops10h 10m

$311

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sat 5/23

2:58 pm-11:55 pm

1 stop6h 57m

Chicago O'Hare Intl

Wed 5/27

9:00 am-2:14 pm

1 stop7h 14m

$313

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Fri 5/29

1:25 pm-10:40 pm

1 stop7h 15m

Chicago Midway

Tue 6/9

5:30 am-9:45 am

1 stop6h 15m

$315

OaklandChicago

OAK - ORD

OAKORD

Oakland

Fri 5/29

12:28 pm-9:50 pm

1 stop7h 22m

Chicago O'Hare Intl

Tue 6/9

7:37 pm-11:54 pm

1 stop6h 17m

$315

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Wed 5/27

9:05 pm-5:00 am

1 stop5h 55m

Chicago Midway

Mon 6/1

6:55 am-12:10 pm

1 stop7h 15m

$316

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 5/27

1:50 pm-10:55 pm

1 stop7h 05m

Chicago O'Hare Intl

Mon 6/1

4:50 pm-11:55 pm

1 stop9h 05m

$316

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 6/2

6:00 am-8:14 pm

2 stops12h 14m

Chicago O'Hare Intl

Tue 6/9

2:07 pm-11:54 pm

2 stops11h 47m

$318

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Fri 5/29

11:55 pm-6:00 am

Nonstop4h 05m

Chicago Midway

Mon 6/1

6:10 pm-10:45 pm

1 stop6h 35m

$319

OaklandChicago

OAK - ORD

OAKORD

Oakland

Fri 6/5

8:13 pm-6:50 pm

1 stop20h 37m

Chicago O'Hare Intl

Mon 6/8

7:59 pm-9:45 am

1 stop15h 46m

$329

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 April is, on average, the cheapest month to fly to Chicago from Oakland, California, with most prices found around $93. If you’re not able to fly to Chicago in April, then June is your next best option. Flight prices from Oakland, California to Chicago during June average around $97.

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 $422. 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 $534.

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 evening. Flights from Oakland, California to Chicago during this time can be as low as $430. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $469.

What is the cheapest Oakland to Chicago flight route?

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

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

You could potentially save up to 27% 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 May 2026, prices for Oakland, California to Chicago flights are approximately 123% 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	$224
Fastest flight time	4h 00m
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 $224. The best round-trip flight deal from Oakland, California to Chicago found on momondo in the last 72 hours is $415.

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

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

There are 3 airports in Chicago. From Oakland, California there are direct flights to Chicago Midway (MDW).

Search flight deals

Frequently asked questions about flying from Oakland, California to Chicago

How far is Oakland to Chicago by plane?
The distance between Oakland and Chicago is about 1845.3 mi. Typically, this will take 4h 00m 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 May 2026, 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) (25.26% of total bookings). The next most popular plane models are Boeing 737 MAX 8 (22.53%), Airbus A321neo (8.87%), and Boeing 737 MAX 9 (6.48%).
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 80% of the total bookings. Other popular airlines include United Airlines with 8%, Spirit Airlines with 7%, 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
United Airlines	PriceFrom $163	Free Cancellation	Rating 7.4 9,684 reviews	Search United Airlines flights
Spirit Airlines	PriceFrom $172	Free Cancellation	Rating 6.3 8,638 reviews	Search Spirit Airlines flights
Alaska Airlines	PriceFrom $237	Free Cancellation	Rating 7.9 12,333 reviews	Search Alaska Airlines flights
Southwest	PriceFrom $246	Free Cancellation	Rating 7.9 4,305 reviews	Search Southwest flights

Southwest Flights From Oakland, California to Chicago
Across 12 Southwest flights from Oakland, California to Chicago this week, the average price was $430, with the best Southwest deals starting from $246 round-trip. 4,305 users have rated Southwest on momondo, with an average score of 7.9/10.

Merrillville

New Buffalo

Hammond

Saint Joseph

Benton Harbor

Portage

Lansing

Valparaiso

Munster

Schererville

Crown Point

Monticello

Chesterton

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.

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Cheap flights from Oakland, California to Chicago from $119

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 5/27. 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 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

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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

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?

What is the cheapest Oakland to Chicago flight route?

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

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

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

What airlines fly to Chicago?

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

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

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

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

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

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

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

Frequently asked questions about flying 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?

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

Airports listed have a maximum distance of 78.5 mi from Chicago

Fly your favorite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

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Popular flights according to clicks in the last 7 days on momondo

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