HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Oakland

$109+ Cheap flights from Chicago (CHI) to Oakland, CA (OAK)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OAK
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Oakland with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Chicago to Oakland are usually found in September or July, booked 30 days in advance, depart on a Monday or Wednesday and return on a Sunday

Cheap flight deals from Chicago to Oakland

Cheapest flights from Chicago to Oakland
Explore the most affordable flight options available from Chicago to Oakland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.

This Delta deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/237:25 amORD - OAK
1 stop6h 29mDelta
Thu 12/2512:34 pmOAK - ORD
1 stop7h 02mDelta
Deal found 12/15$463
This Southwest deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/252:15 pmORD - OAK
1 stop8h 20mSouthwest
Mon 1/192:10 pmOAK - ORD
1 stop6h 25mSouthwest
Deal found 12/17$492
This Southwest deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/233:05 pmORD - OAK
2 stops8h 55mSouthwest
Thu 12/257:00 amOAK - ORD
1 stop6h 25mSouthwest
Deal found 12/15$518
This Delta deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/197:20 amORD - OAK
1 stop6h 30mDelta
Tue 1/205:55 amOAK - ORD
1 stop5h 43mDelta
Deal found 12/17$524
This Delta deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/177:40 pmORD - OAK
1 stop6h 28mDelta
Thu 1/225:55 amOAK - ORD
2 stops10h 00mDelta
Deal found 12/16$529
This Southwest deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3112:55 pmMDW - OAK
1 stop8h 00mSouthwest
Sun 1/48:25 amOAK - MDW
2 stops7h 15mSouthwest
Deal found 12/16$533
This Southwest deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/252:15 pmORD - OAK
1 stop8h 20mSouthwest
Sun 1/47:15 pmOAK - ORD
2 stops15h 45mSouthwest
Deal found 12/16$539
This Southwest deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/314:25 pmORD - OAK
1 stop7h 20mSouthwest
Sun 1/47:15 pmOAK - ORD
2 stops15h 45mSouthwest
Deal found 12/16$568
This Delta deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/217:05 pmORD - OAK
1 stop6h 53mDelta
Thu 12/2512:34 pmOAK - ORD
1 stop7h 02mDelta
Deal found 12/16$583
This Southwest deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/249:35 amMDW - OAK
1 stop9h 00mSouthwest
Sun 12/285:25 amOAK - MDW
Nonstop4h 05mSouthwest
Deal found 12/16$613
This Delta deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/171:14 pmMDW - OAK
2 stops12h 54mDelta
Thu 1/225:55 amOAK - MDW
2 stops10h 41mDelta
Deal found 12/16$654

Find flight deals from Chicago to Oakland

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Oakland (OAK). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$249
(Delta)

One-way from

$109
(Southwest)

Popular in

November

Cheapest in

September

Average price

$562

Good round-trip deal

$537 or less

Good one-way deal

$323 or less
Provider with most accurate pricing for Chicago (CHI)-Oakland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Oakland flights.
Search Deals
From Chicago (CHI) to Oakland
Search Deals
One-way flight from Chicago (CHI) to Oakland
Search Deals
Highest demand for flights based on searches. 32% potential increase in price ($187 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($29 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Oakland.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Oakland.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Oakland that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 18, 2025.
Use the filters below to find and compare flights from Chicago to Oakland that are best for you.

Fly from

Chicago

Fly to

Oakland

Route

Depart

Return

Price

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Wed 1/7

7:20 am-11:57 am

1 stop6h 37m

Oakland

Sat 1/17

12:38 pm-9:52 pm

1 stop7h 14m

$249

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Tue 1/20

8:15 am-3:55 pm

1 stop9h 40m

Oakland

Fri 1/23

11:10 am-5:15 pm

Nonstop4h 05m

$258

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Wed 1/21

6:40 pm-11:53 pm

1 stop7h 13m

Oakland

Wed 1/28

12:33 pm-9:52 pm

1 stop7h 19m

$261

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Sun 1/18

8:10 am-2:55 pm

1 stop8h 45m

Oakland

Thu 1/22

9:30 am-6:50 pm

1 stop7h 20m

$268

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Sun 1/18

8:10 am-2:55 pm

1 stop8h 45m

Oakland

Fri 1/23

5:25 am-2:45 pm

1 stop7h 20m

$268

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Fri 1/23

5:05 am-10:05 am

1 stop7h 00m

Oakland

Tue 1/27

11:10 am-5:15 pm

Nonstop4h 05m

$270

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Thu 2/19

3:54 pm-10:49 pm

1 stop8h 55m

Oakland

Tue 2/24

6:15 am-4:33 pm

1 stop8h 18m

$271

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Fri 1/23

8:00 am-8:40 pm

1 stop14h 40m

Oakland

Tue 1/27

8:10 am-11:50 pm

1 stop13h 40m

$271

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Wed 1/7

1:00 pm-7:50 pm

2 stops8h 50m

Oakland

Sat 1/17

2:05 pm-10:35 pm

1 stop6h 30m

$273

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Wed 1/28

8:00 am-4:23 pm

1 stop10h 23m

Oakland

Sat 1/31

11:08 am-11:50 pm

1 stop10h 42m

$277

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 38 results
1
2
3
4

Compare providers for flights from Chicago to Oakland

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Oakland in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Oakland, California flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Oakland, California flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago-Oakland, California flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Oakland, California flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Oakland, California flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Oakland

Have a flexible travel schedule? Discover the best time to fly to Oakland from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Oakland

How far ahead should I book a flight from Chicago to Oakland, California?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Oakland. Price data was last updated on December 12, 2025.

To ensure you get the cheapest price possible for a flight from Chicago to Oakland, California, you should look to book at least 30 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Chicago to Oakland, California?

Currently, October is the cheapest month in which you can book a flight from Chicago to Oakland, California (average of $80). Flying from Chicago to Oakland, California in November is currently the most expensive (average of $207). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to OAK?

Find hourly flight availability from Chicago to Oakland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 18, 2025.

It’s typically best to fly out from Chicago to Oakland, California in the afternoon. Doing so could potentially save you 33% on the flight price compared to flying in the morning, which is usually more expensive.

What is the cheapest day to fly from Chicago to Oakland, California?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Oakland. Price data was last updated on December 13, 2025.

Travelers seeking maximum savings on their Chicago to Oakland, California flight should consider departing on Sunday afternoons when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

What’s the top layover airport for flights from Chicago to Oakland, California?

Share of 1-stop round-trip flights from Chicago to Oakland, California chosen by Cheapflights users in the past 12 months, using the same layover each way.

Denver (DEN) – chosen by Cheapflights users on 50% of 1-stop itineraries from Chicago to Oakland, California on Cheapflights.

What’s the cheapest layover airport for flights from Chicago to Oakland, California?

Average round-trip fare for 1-stop flights from Chicago to Oakland, California, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Las Vegas (LAS) is the most affordable 1-stop option, with an average round-trip price of $300.

What’s the fastest layover option from Chicago to Oakland, California?

Shortest average travel time for 1-stop one-way flights from Chicago to Oakland, California, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Denver (DEN) have the shortest average one-way travel time for 1-stop routes: 9h 45m.

Which airport typically offers the quickest layover for flights from Chicago to Oakland, California?

Average layover duration for 1-stop one-way flights from Chicago to Oakland, California, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Denver (DEN) offer the fastest connection on this route, with an average layover time of 3h 18m.

How often are flights from Chicago to Oakland delayed?

About 22% of weekly flights between Chicago and Oakland have experienced delays in the past year, with the average delay time being 99 minutes.

What is the most punctual flight time for Chicago to Oakland flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Wednesday tends to have the lowest number of delays on this route, whereas Monday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Chicago to Oakland flights?

Over the last year, Southwest have had the lowest number of delays on this route, with just 24% of flights being delayed.

The best insider tips for Chicago to Oakland flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago to Oakland trip
Airports
MDW

Use the Orange Line to reach MDW quickly; it's a cost-effective and efficient option for travelers heading to the airport.

Read more about MDWBy Ramsey Qubein
OAK

Consider using BART for cost-efficient travel from OAK to San Francisco, especially during rush hour.

Read more about OAKBy Bill Fink
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Bill Fink

Bill Fink

Expert on OAK

Bill Fink

Bill Fink

Bill is an award-winning travel writer with extensive credits covering airlines and the aviation industry for publications including AARP, AFAR, The Points Guy and Yahoo. Based in Portland, Oregon, Bill has traveled to more than 75 countries - and been late for his flight in most of them. He once achieved top-level frequent flier status for all of American, Delta and United Airlines during a single year.

Read more

Reviews of airlines servicing Oakland

Get insights into the airlines that provide service to Oakland. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Oakland. Reviews last updated December 18, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from Chicago to Oakland by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,250 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

7.9

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

7.9

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Delta
7.9
Good
8,009 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

7.9

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
United Airlines
7.4
Good
9,093 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

7.9

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Spirit Airlines
6.3
Okay
8,190 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

7.9

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Oakland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Oakland from Chicago?

    Located just 7.0 mi from the city center, Oakland is the airport most travelers will use when flying to Oakland from Chicago. Booking flights from Chicago to Oakland (OAK) should be relatively easy as there are 0 daily inbound flights from Chicago from 2 different airlines.

  • How long is the flight from Chicago to Oakland, California?

    A quick flight from Chicago to Oakland, California can take about 6h 37m. Delta provides one of the quickest options available for as low as $249. The distance between Chicago and Oakland, California is about 1830 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Chicago to Oakland, California round-trip?

    Our cheapest airline available from Chicago to Oakland, California is Spirit Airlines. Our recent data shows that you can find tickets from as low as $53 on this airline. An additional option worth looking into is Southwest, starting at $236. These flights start at 86% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Chicago to Oakland, California one-way?

    The cheapest airline one-way is Alaska Airlines, with whom users have recently found tickets for as low as $98. However, be on the lookout for offers from Southwest and Delta, as they are both options that can get you from Chicago to Oakland, California for a low price.

  • Can I find deals for flights from Chicago to Oakland that include hotel bookings?

    Yes. In addition to deals on Chicago to Oakland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Oakland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Oakland.

  • Can I find deals for business class flights from Chicago to Oakland?

    Yes. Cheapflights offers flight deals from Chicago to Oakland by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Oakland, California?

    Currently, October is the cheapest month in which you can book a flight from Chicago to Oakland, California (average of $80). Flying from Chicago to Oakland, California in November is currently the most expensive (average of $207). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Oakland

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Las Vegas flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to San Francisco flights
Midway to Los Angeles flights
Midway to Las Vegas flights
O'Hare Intl to Santa Ana flights
O'Hare Intl to Ontario flights
O'Hare Intl to San Diego flights
St. Louis to Las Vegas flights
O'Hare Intl to Palm Springs flights
O'Hare Intl to Burbank flights
Midway to San Francisco flights
Midway to Santa Ana flights
St. Louis to Los Angeles flights
O'Hare Intl to Reno flights
Midway to San Diego flights
O'Hare Intl to Sacramento flights
Rockford to Las Vegas flights
Midway to Ontario flights
O'Hare Intl to San Jose flights
Midway to Palm Springs flights
Midway to Burbank flights
St. Louis to San Diego flights
O'Hare Intl to Long Beach flights
St. Louis to San Francisco flights
O'Hare Intl to Oakland flights
St. Louis to Ontario flights
Midway to San Jose flights
Midway to Reno flights
St. Louis to Burbank flights
Peoria to Las Vegas flights
St. Louis to Santa Ana flights
Midway to Sacramento flights
O'Hare Intl to Santa Barbara flights
Moline to Los Angeles flights
O'Hare Intl to Fresno flights
Moline to Las Vegas flights
Midway to Oakland flights
Bloomington to Las Vegas flights
Peoria to San Diego flights
Midway to Long Beach flights
Peoria to Los Angeles flights
St. Louis to San Jose flights
St. Louis to Sacramento flights
Moline to San Jose flights
St. Louis to Long Beach flights
Evansville to Las Vegas flights
St. Louis to Palm Springs flights
Moline to San Francisco flights
O'Hare Intl to Monterey flights

Top 2 airlines flying from Chicago to Oakland

Discover the top 2 airlines that operate flights from Chicago to Oakland. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$83Average$223FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$236Average$432FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.