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 $224.

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

Las Vegas (LAS) was the most common stop: 67% 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?

2 flights are operational daily from Oakland, California to Chicago as of November 2026. The most popular departure time for this route is 5:00AM, with 66% of flights per day taking off in the evening.

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 20m.

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

Southwest, Frontier, 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 week?

As of November 2026, 15 flights take off from Oakland, California and land in Chicago each week. The most common flight departure day for this route is Mon, with 20% 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 48% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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

Las Vegas (LAS) has the shortest average layover time for this route: 0h 58m.

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 November 2026, there are 3 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.

$114 Cheap Flights from Oakland, California to Chicago in 2026/27

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.

12:28 pm - 4:59 amOAK Oakland-ORD Chicago O'Hare Intl

14h 31m1 stop Las Vegas Harry Reid Intl

10:00 am - 11:33 amORD Chicago O'Hare Intl-OAK Oakland

27h 33m2 stops Dallas/Fort Worth Las Vegas Harry Reid Intl

$234Frontier

Thu, Dec 3 - Tue, Dec 8

12:28 pm - 4:59 amOAK Oakland-ORD Chicago O'Hare Intl

14h 31m1 stop Las Vegas Harry Reid Intl

6:21 am - 11:33 amORD Chicago O'Hare Intl-OAK Oakland

7h 12m1 stop Las Vegas Harry Reid Intl

$246Frontier

Thu, Dec 3 - Mon, Dec 7

12:28 pm - 4:59 amOAK Oakland-ORD Chicago O'Hare Intl

14h 31m1 stop Las Vegas Harry Reid Intl

6:21 am - 11:33 amORD Chicago O'Hare Intl-OAK Oakland

7h 12m1 stop Las Vegas Harry Reid Intl

$246Frontier

Thu, Dec 3 - Thu, Dec 10

12:28 pm - 4:59 amOAK Oakland-ORD Chicago O'Hare Intl

14h 31m1 stop Las Vegas Harry Reid Intl

10:00 am - 11:33 amORD Chicago O'Hare Intl-OAK Oakland

27h 33m2 stops Dallas/Fort Worth Las Vegas Harry Reid Intl

$247Frontier

Wed, Dec 2 - Tue, Dec 8

6:35 am - 12:40 pmOAK Oakland-MDW Chicago Midway

4h 05mnonstop

1:00 pm - 3:45 pmMDW Chicago Midway-OAK Oakland

4h 45mnonstop

$297Southwest

Thu, Jan 21 - Sat, Jan 23

11:50 pm - 5:55 amOAK Oakland-MDW Chicago Midway

4h 05mnonstop

8:45 pm - 11:35 pmMDW Chicago Midway-OAK Oakland

4h 50mnonstop

$297Southwest

Thu, Dec 3 - Mon, Dec 7

5:55 am - 12:00 pmOAK Oakland-MDW Chicago Midway

4h 05mnonstop

8:10 pm - 11:00 pmMDW Chicago Midway-OAK Oakland

4h 50mnonstop

$297Southwest

Thu, Feb 25 - Sat, Feb 27

6:30 am - 12:30 pmOAK Oakland-MDW Chicago Midway

4h 00mnonstop

8:45 pm - 11:35 pmMDW Chicago Midway-OAK Oakland

4h 50mnonstop

$297Southwest

Mon, Dec 7 - Mon, Dec 7

10:36 am - 7:00 pmOAK Oakland-ORD Chicago O'Hare Intl

6h 24m1 stop San Diego

2:08 pm - 7:39 pmORD Chicago O'Hare Intl-OAK Oakland

7h 31m1 stop Portland

$307Alaska Airlines

Thu, Dec 3 - Tue, Dec 8

7:00 am - 4:31 pmOAK Oakland-ORD Chicago O'Hare Intl

7h 31m1 stop Seattle/Tacoma Intl

2:08 pm - 7:39 pmORD Chicago O'Hare Intl-OAK Oakland

7h 31m1 stop Portland

$307Alaska Airlines

Wed, Dec 2 - Tue, Dec 8

Cheap last minute flights

Enter your travel dates to find the best prices.

10:18 am - 5:13 amOAK Oakland-ORD Chicago O'Hare Intl

16h 55m1 stop Las Vegas Harry Reid Intl

5:15 pm - 11:53 amORD Chicago O'Hare Intl-OAK Oakland

20h 38m1 stop Las Vegas Harry Reid Intl

$376Frontier

Fri, Nov 13 - Mon, Nov 16

10:18 am - 5:13 amOAK Oakland-ORD Chicago O'Hare Intl

16h 55m1 stop Las Vegas Harry Reid Intl

5:15 pm - 9:23 amORD Chicago O'Hare Intl-OAK Oakland

18h 08m1 stop Las Vegas Harry Reid Intl

$382Frontier

Thu, Nov 12 - Sun, Nov 15

5:55 pm - 5:13 amOAK Oakland-ORD Chicago O'Hare Intl

9h 18m1 stop Las Vegas Harry Reid Intl

5:15 pm - 11:53 amORD Chicago O'Hare Intl-OAK Oakland

20h 38m1 stop Las Vegas Harry Reid Intl

$391Frontier

Fri, Nov 13 - Mon, Nov 16

10:18 am - 5:13 amOAK Oakland-ORD Chicago O'Hare Intl

16h 55m1 stop Las Vegas Harry Reid Intl

5:15 pm - 11:53 amORD Chicago O'Hare Intl-OAK Oakland

20h 38m1 stop Las Vegas Harry Reid Intl

$396Frontier

Mon, Nov 9 - Fri, Nov 13

6:12 pm - 1:17 pmOAK Oakland-ORD Chicago O'Hare Intl

17h 05m1 stop San Diego

6:35 pm - 12:01 pmORD Chicago O'Hare Intl-OAK Oakland

19h 26m1 stop Seattle/Tacoma Intl

$533Alaska Airlines

Sat, Nov 14 - Tue, Nov 17

10:00 am - 6:59 pmOAK Oakland-ORD Chicago O'Hare Intl

6h 59m1 stop San Diego

2:07 pm - 9:19 pmORD Chicago O'Hare Intl-OAK Oakland

9h 12m1 stop Portland

$533Alaska Airlines

Tue, Nov 10 - Wed, Nov 11

5:35 am - 11:35 amOAK Oakland-MDW Chicago Midway

4h 00mnonstop

9:55 pm - 12:40 amMDW Chicago Midway-OAK Oakland

4h 45mnonstop

$537Southwest

Fri, Nov 13 - Sun, Nov 15

11:50 pm - 5:55 amOAK Oakland-MDW Chicago Midway

4h 05mnonstop

8:45 pm - 11:35 pmMDW Chicago Midway-OAK Oakland

4h 50mnonstop

$537Southwest

Mon, Nov 9 - Wed, Nov 11

11:50 pm - 5:55 amOAK Oakland-MDW Chicago Midway

4h 05mnonstop

8:45 pm - 11:35 pmMDW Chicago Midway-OAK Oakland

4h 50mnonstop

$537Southwest

Wed, Nov 11 - Mon, Nov 16

11:50 pm - 5:55 amOAK Oakland-MDW Chicago Midway

4h 05mnonstop

9:55 pm - 12:40 amMDW Chicago Midway-OAK Oakland

4h 45mnonstop

$537Southwest

Thu, Nov 12 - Sun, Nov 15

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Alaska Airlines flights from Oakland, California to Chicago

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

Alaska Airlines

Dec 4

OAK1:36 pmOakland

8h 23m

1 stop

ORD11:59 pmChicago O'Hare Intl

Dec 7

ORD6:00 amChicago O'Hare Intl

15h 12m

1 stop

OAK7:12 pmOakland

$335

Alaska Airlines

Dec 17

OAK6:44 amOakland

10h 10m

1 stop

ORD6:54 pmChicago O'Hare Intl

Dec 21

ORD7:58 pmChicago O'Hare Intl

17h 15m

1 stop

OAK11:13 amOakland

$338

Alaska Airlines

Dec 8

OAK7:00 amOakland

8h 49m

1 stop

ORD5:49 pmChicago O'Hare Intl

Dec 9

ORD2:08 pmChicago O'Hare Intl

7h 31m

1 stop

OAK7:39 pmOakland

$339

Frontier flights from Oakland, California to Chicago

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

Frontier

Dec 3

OAK12:28 pmOakland

14h 31m

1 stop

ORD4:59 amChicago O'Hare Intl

Dec 8

ORD10:00 amChicago O'Hare Intl

27h 33m

2 stops

OAK11:33 amOakland

$234

Frontier

Dec 3

OAK12:28 pmOakland

14h 31m

1 stop

ORD4:59 amChicago O'Hare Intl

Dec 7

ORD6:21 amChicago O'Hare Intl

7h 12m

1 stop

OAK11:33 amOakland

$246

Frontier

Dec 2

OAK12:28 pmOakland

14h 31m

1 stop

ORD4:59 amChicago O'Hare Intl

Dec 8

ORD10:00 amChicago O'Hare Intl

27h 33m

2 stops

OAK11:33 amOakland

$247

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

OaklandChicago

OAK Oakland - ORD Chicago O'Hare Intl

OAKORD

Oakland

Thu 12/3

12:28 pm-4:59 am

1 stop14h 31m

Chicago O'Hare Intl

Tue 12/8

10:00 am-11:33 am

2 stops27h 33m

$234

OaklandChicago

OAK Oakland - ORD Chicago O'Hare Intl

OAKORD

Oakland

Thu 12/3

12:28 pm-4:59 am

1 stop14h 31m

Chicago O'Hare Intl

Mon 12/7

6:21 am-11:33 am

1 stop7h 12m

$246

OaklandChicago

OAK Oakland - ORD Chicago O'Hare Intl

OAKORD

Oakland

Thu 12/3

12:28 pm-4:59 am

1 stop14h 31m

Chicago O'Hare Intl

Thu 12/10

6:21 am-11:33 am

1 stop7h 12m

$246

OaklandChicago

OAK Oakland - ORD Chicago O'Hare Intl

OAKORD

Oakland

Wed 12/2

12:28 pm-4:59 am

1 stop14h 31m

Chicago O'Hare Intl

Tue 12/8

10:00 am-11:33 am

2 stops27h 33m

$247

Quickest round-trip

OaklandChicago

OAK Oakland - MDW Chicago Midway

OAKMDW

Oakland

Thu 1/21

6:35 am-12:40 pm

Nonstop4h 05m

Chicago Midway

Sat 1/23

1:00 pm-3:45 pm

Nonstop4h 45m

$297

OaklandChicago

OAK Oakland - MDW Chicago Midway

OAKMDW

Oakland

Thu 12/3

11:50 pm-5:55 am

Nonstop4h 05m

Chicago Midway

Mon 12/7

8:45 pm-11:35 pm

Nonstop4h 50m

$297

OaklandChicago

OAK Oakland - MDW Chicago Midway

OAKMDW

Oakland

Thu 2/25

5:55 am-12:00 pm

Nonstop4h 05m

Chicago Midway

Sat 2/27

8:10 pm-11:00 pm

Nonstop4h 50m

$297

OaklandChicago

OAK Oakland - MDW Chicago Midway

OAKMDW

Oakland

Mon 12/7

6:30 am-12:30 pm

Nonstop4h 00m

Chicago Midway

Mon 12/7

8:45 pm-11:35 pm

Nonstop4h 50m

$297

OaklandChicago

OAK Oakland - ORD Chicago O'Hare Intl

OAKORD

Oakland

Thu 12/3

10:36 am-7:00 pm

1 stop6h 24m

Chicago O'Hare Intl

Tue 12/8

2:08 pm-7:39 pm

1 stop7h 31m

$307

OaklandChicago

OAK Oakland - ORD Chicago O'Hare Intl

OAKORD

Oakland

Wed 12/2

7:00 am-4:31 pm

1 stop7h 31m

Chicago O'Hare Intl

Tue 12/8

2:08 pm-7:39 pm

1 stop7h 31m

$307

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?

Prices are currently low for flights on this route.

Typical prices usually range from $512 to $714.
The lowest price recently found on this route was $234.

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 $335. If you’re not able to fly to Chicago in February, then May is your next best option. Flight prices from Oakland, California to Chicago during May average around $399.

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 $454. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Oakland, California to Chicago for around $597.

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 $480. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $528.

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, California to Chicago flights?

There is only 1 cabin class available to choose from on Oakland, California 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 44% 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 November 2026, prices for Oakland, California to Chicago flights are approximately 91% 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	$114
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 $114. The best round-trip flight deal from Oakland, California to Chicago found on momondo in the last 72 hours is $234.

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 November 2026, there are 3 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 (25.17% of total bookings). The next most popular plane models are Boeing 737-800 (10.84%), Boeing 737-800 Passenger/BBJ2 (winglets) (10.49%), and Airbus A321-100/200 (8.04%).
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 91% of the total bookings. Other popular airlines include United Airlines with 9%.

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
Alaska Airlines	PriceFrom $272	Free Cancellation	Rating 7.9 13,156 reviews		Search Alaska Airlines flights
Southwest	PriceFrom $275	Free Cancellation	Rating 8.0 4,215 reviews		Search Southwest flights

Southwest Flights From Oakland, California to Chicago
Across 15 Southwest flights from Oakland, California to Chicago this week, the average price was $441, with the best Southwest deals starting from $275 round-trip. 4,216 users have rated Southwest on momondo, with an average score of 8.0/10.

Merrillville

New Buffalo

Hammond

Portage

Lansing

Benton Harbor

Saint Joseph

Valparaiso

Schererville

Munster

Chesterton

Monticello

Crown Point

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

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Nearby airports

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Complete your trip

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Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

Cheap flights from Oakland, California to Chicago from $114

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 1/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Find the cheapest flights from Oakland, California to Chicago

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Big names and deals

Big names and deals

Filter for what you want

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Alaska Airlines flights from Oakland, California to Chicago

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

Frontier flights from Oakland, California to Chicago

Our best Frontier 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

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?

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

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

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

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.

Popular cities in the United States

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

Fly to other destinations from Oakland, California

According to popular flight searches on momondo this year

Complete your trip to Chicago

Explore popular destinations other users love

According to popular flight searches on momondo this year