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 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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 August 2026. The most popular departure time for this route is 11:00PM, with 43% of flights per day taking off in the evening.

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

As of August 2026, 20 flights take off from Oakland, California and land in Chicago each week. The most common flight departure day for this route is Sun, with 25% of weekly flights taking off on this day.

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

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

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 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.

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

Las Vegas (LAS) was the most common stop: 50% of momondo users choosing 1-stop flights on this route connected there.

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.

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 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.

$89 Cheap Flights from Oakland, California to Chicago in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Oakland, California to Chicago

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6:51 pm - 5:38 amOAK Oakland-ORD Chicago O'Hare Intl

8h 47m1 stop Las Vegas Harry Reid Intl

8:55 pm - 5:56 pmORD Chicago O'Hare Intl-OAK Oakland

23h 01m1 stop Las Vegas Harry Reid Intl

$178Frontier

Thu, Sep 17 - Thu, Sep 24

8:39 pm - 11:57 amOAK Oakland-ORD Chicago O'Hare Intl

13h 18m1 stop Las Vegas Harry Reid Intl

6:50 am - 11:18 amORD Chicago O'Hare Intl-OAK Oakland

6h 28m1 stop Las Vegas Harry Reid Intl

$178Frontier

Thu, Oct 15 - Tue, Oct 20

6:51 pm - 5:38 amOAK Oakland-ORD Chicago O'Hare Intl

8h 47m1 stop Las Vegas Harry Reid Intl

8:55 pm - 11:51 amORD Chicago O'Hare Intl-OAK Oakland

16h 56m1 stop Las Vegas Harry Reid Intl

$178Frontier

Thu, Sep 17 - Mon, Sep 21

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

4h 00mnonstop

9:30 pm - 12:10 amMDW Chicago Midway-OAK Oakland

4h 40mnonstop

$219Southwest

Mon, Sep 28 - Thu, Oct 1

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

4h 00mnonstop

8:20 am - 2:00 pmMDW Chicago Midway-OAK Oakland

7h 40m1 stop Dallas Love Field

$229Southwest

Mon, Sep 14 - Wed, Sep 16

2:30 pm - 11:50 pmOAK Oakland-MDW Chicago Midway

7h 20m1 stop San Diego

9:30 pm - 12:10 amMDW Chicago Midway-OAK Oakland

4h 40mnonstop

$229Southwest

Mon, Sep 28 - Thu, Oct 1

6:00 am - 6:19 pmOAK Oakland-MDW Chicago Midway

10h 19m2 stops Salt Lake City Minneapolis St Paul

9:59 am - 4:20 pmMDW Chicago Midway-OAK Oakland

8h 21m2 stops Minneapolis St Paul Salt Lake City

$249Delta

Wed, Sep 30 - Sat, Oct 3

5:00 pm - 9:40 amOAK Oakland-ORD Chicago O'Hare Intl

14h 40m2 stops Salt Lake City Atlanta Hartsfield-Jackson

5:10 pm - 11:59 pmORD Chicago O'Hare Intl-OAK Oakland

8h 49m2 stops Detroit Metropolitan Wayne County Salt Lake City

$267Delta

Sat, Sep 5 - Fri, Sep 11

3:13 pm - 1:22 pmOAK Oakland-ORD Chicago O'Hare Intl

20h 09m1 stop San Diego

8:17 pm - 11:06 amORD Chicago O'Hare Intl-OAK Oakland

16h 49m1 stop San Diego

$277Alaska Airlines

Wed, Aug 26 - Mon, Aug 31

3:13 pm - 11:59 pmOAK Oakland-ORD Chicago O'Hare Intl

6h 46m1 stop San Diego

7:20 am - 2:33 pmORD Chicago O'Hare Intl-OAK Oakland

9h 13m1 stop San Diego

$277Alaska Airlines

Thu, Sep 10 - Thu, Sep 17

Cheap last minute flights

Enter your travel dates to find the best prices.

7:50 am - 5:00 pmOAK Oakland-MDW Chicago Midway

7h 10m1 stop Long Beach Municipal

8:35 pm - 11:05 pmMDW Chicago Midway-OAK Oakland

4h 30mnonstop

$483Southwest

Wed, Aug 12 - Tue, Aug 18

7:45 pm - 5:40 amOAK Oakland-MDW Chicago Midway

7h 55m1 stop Las Vegas Harry Reid Intl

1:55 pm - 4:20 pmMDW Chicago Midway-OAK Oakland

4h 25mnonstop

$483Southwest

Wed, Aug 12 - Sat, Aug 15

2:50 pm - 1:21 pmOAK Oakland-ORD Chicago O'Hare Intl

20h 31m1 stop San Diego

5:42 pm - 9:23 amORD Chicago O'Hare Intl-OAK Oakland

17h 41m1 stop Seattle/Tacoma Intl

$493Alaska Airlines

Sat, Aug 15 - Tue, Aug 18

8:55 am - 7:10 pmOAK Oakland-MDW Chicago Midway

8h 15m1 stop Austin Bergstrom

2:15 pm - 7:50 pmMDW Chicago Midway-OAK Oakland

7h 35m1 stop Denver Intl

$493Southwest

Wed, Aug 12 - Tue, Aug 18

7:45 pm - 5:50 amOAK Oakland-MDW Chicago Midway

8h 05m1 stop Phoenix Sky Harbor Intl

2:40 pm - 7:00 pmMDW Chicago Midway-OAK Oakland

6h 20m1 stop Burbank Bob Hope

$493Southwest

Wed, Aug 12 - Sat, Aug 15

5:35 pm - 5:00 amOAK Oakland-ORD Chicago O'Hare Intl

9h 25m1 stop Portland

5:59 pm - 10:41 pmORD Chicago O'Hare Intl-OAK Oakland

6h 42m1 stop San Diego

$505Alaska Airlines

Wed, Aug 12 - Sat, Aug 15

7:52 am - 5:00 amOAK Oakland-ORD Chicago O'Hare Intl

19h 08m1 stop Portland

7:59 pm - 11:06 amORD Chicago O'Hare Intl-OAK Oakland

17h 07m1 stop San Diego

$505Alaska Airlines

Tue, Aug 11 - Tue, Aug 18

6:00 am - 5:41 pmOAK Oakland-ORD Chicago O'Hare Intl

9h 41m2 stops Salt Lake City Minneapolis St Paul

7:44 pm - 11:56 pmORD Chicago O'Hare Intl-OAK Oakland

6h 12m1 stop Salt Lake City

$532Delta

Sat, Aug 15 - Mon, Aug 17

6:00 am - 4:17 pmOAK Oakland-ORD Chicago O'Hare Intl

8h 17m2 stops Salt Lake City Detroit Metropolitan Wayne County

7:48 am - 11:52 amORD Chicago O'Hare Intl-OAK Oakland

6h 04m1 stop Salt Lake City

$541Delta

Wed, Aug 12 - Sat, Aug 15

6:00 am - 6:33 pmOAK Oakland-MDW Chicago Midway

10h 33m2 stops Salt Lake City Detroit Metropolitan Wayne County

1:51 pm - 10:38 pmMDW Chicago Midway-OAK Oakland

10h 47m2 stops Minneapolis St Paul Salt Lake City

$546Delta

Wed, Aug 12 - Sat, Aug 15

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Frontier flights from Oakland, California to Chicago

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

Frontier

Sep 17

OAK6:51 pmOakland

8h 47m

1 stop

ORD5:38 amChicago O'Hare Intl

Sep 21

ORD8:55 pmChicago O'Hare Intl

16h 56m

1 stop

OAK11:51 amOakland

$178

Frontier

Sep 14

OAK10:17 amOakland

17h 21m

1 stop

ORD5:38 amChicago O'Hare Intl

Sep 15

ORD1:21 pmChicago O'Hare Intl

24h 30m

1 stop

OAK11:51 amOakland

$188

Frontier

Sep 9

OAK12:47 pmOakland

14h 51m

1 stop

ORD5:38 amChicago O'Hare Intl

Sep 11

ORD8:55 pmChicago O'Hare Intl

16h 56m

1 stop

OAK11:51 amOakland

$208

Alaska Airlines flights from Oakland, California to Chicago

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

Alaska Airlines

Sep 10

OAK6:48 amOakland

10h 33m

1 stop

ORD7:21 pmChicago O'Hare Intl

Sep 14

ORD8:17 pmChicago O'Hare Intl

16h 49m

1 stop

OAK11:06 amOakland

$277

Alaska Airlines

Sep 5

OAK5:10 pmOakland

18h 12m

1 stop

ORD1:22 pmChicago O'Hare Intl

Sep 11

ORD2:18 pmChicago O'Hare Intl

10h 52m

1 stop

OAK11:10 pmOakland

$283

Alaska Airlines

Sep 11

OAK3:13 pmOakland

6h 46m

1 stop

ORD11:59 pmChicago O'Hare Intl

Sep 16

ORD7:20 amChicago O'Hare Intl

9h 13m

1 stop

OAK2:33 pmOakland

$284

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 9/17

6:51 pm-5:38 am

1 stop8h 47m

Chicago O'Hare Intl

Thu 9/24

8:55 pm-5:56 pm

1 stop23h 01m

$178

OaklandChicago

OAK Oakland - ORD Chicago O'Hare Intl

OAKORD

Oakland

Thu 10/15

8:39 pm-11:57 am

1 stop13h 18m

Chicago O'Hare Intl

Tue 10/20

6:50 am-11:18 am

1 stop6h 28m

$178

OaklandChicago

OAK Oakland - ORD Chicago O'Hare Intl

OAKORD

Oakland

Thu 9/17

6:51 pm-5:38 am

1 stop8h 47m

Chicago O'Hare Intl

Mon 9/21

8:55 pm-11:51 am

1 stop16h 56m

$178

Quickest round-trip

OaklandChicago

OAK Oakland - MDW Chicago Midway

OAKMDW

Oakland

Mon 9/28

11:55 pm-5:55 am

Nonstop4h 00m

Chicago Midway

Thu 10/1

9:30 pm-12:10 am

Nonstop4h 40m

$219

OaklandChicago

OAK Oakland - MDW Chicago Midway

OAKMDW

Oakland

Mon 9/14

11:55 pm-5:55 am

Nonstop4h 00m

Chicago Midway

Wed 9/16

8:20 am-2:00 pm

1 stop7h 40m

$229

OaklandChicago

OAK Oakland - MDW Chicago Midway

OAKMDW

Oakland

Mon 9/28

2:30 pm-11:50 pm

1 stop7h 20m

Chicago Midway

Thu 10/1

9:30 pm-12:10 am

Nonstop4h 40m

$229

OaklandChicago

OAK Oakland - MDW Chicago Midway

OAKMDW

Oakland

Wed 9/30

6:00 am-6:19 pm

2 stops10h 19m

Chicago Midway

Sat 10/3

9:59 am-4:20 pm

2 stops8h 21m

$249

OaklandChicago

OAK Oakland - ORD Chicago O'Hare Intl

OAKORD

Oakland

Sat 9/5

5:00 pm-9:40 am

2 stops14h 40m

Chicago O'Hare Intl

Fri 9/11

5:10 pm-11:59 pm

2 stops8h 49m

$267

OaklandChicago

OAK Oakland - ORD Chicago O'Hare Intl

OAKORD

Oakland

Wed 8/26

3:13 pm-1:22 pm

1 stop20h 09m

Chicago O'Hare Intl

Mon 8/31

8:17 pm-11:06 am

1 stop16h 49m

$277

OaklandChicago

OAK Oakland - ORD Chicago O'Hare Intl

OAKORD

Oakland

Thu 9/10

3:13 pm-11:59 pm

1 stop6h 46m

Chicago O'Hare Intl

Thu 9/17

7:20 am-2:33 pm

1 stop9h 13m

$277

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 $364 to $587.
The lowest price recently found on this route was $178.

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 $364. If you’re not able to fly to Chicago in February, then September is your next best option. Flight prices from Oakland, California to Chicago during September average around $383.

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 $443. 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 $576.

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 $470. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $510.

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 22% 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 2026, prices for Oakland, California to Chicago flights are approximately 114% 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	$208
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 $208. The best round-trip flight deal from Oakland, California to Chicago found on momondo in the last 72 hours is $372.

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 August 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) (21.64% of total bookings). The next most popular plane models are Boeing 737 MAX 8 (16.72%), Boeing 737-800 (7.54%), and Airbus A321-100/200 (7.54%).
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 89% of the total bookings. Other popular airlines include United Airlines with 7% and Alaska Airlines with 4%.

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
Delta	PriceFrom $148	Free Cancellation	Rating 7.8 8,497 reviews	Search Delta flights
United Airlines	PriceFrom $207	Free Cancellation	Rating 7.4 10,099 reviews	Search United Airlines flights
Southwest	PriceFrom $269	Free Cancellation	Rating 8.0 4,218 reviews	Search Southwest flights
Alaska Airlines	PriceFrom $272	Free Cancellation	Rating 7.9 12,794 reviews	Search Alaska Airlines flights

Southwest Flights From Oakland, California to Chicago
Across 20 Southwest flights from Oakland, California to Chicago this week, the average price was $439, with the best Southwest deals starting from $269 round-trip. 4,218 users have rated Southwest on momondo, with an average score of 8.0/10.

Merrillville

New Buffalo

Hammond

Portage

Benton Harbor

Lansing

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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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 $89

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 9/21. 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

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Filter for what you want

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Frontier flights from Oakland, California to Chicago

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

Alaska Airlines flights from Oakland, California to Chicago

Our best Alaska Airlines 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