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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 4/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OAK
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Find cheap flights from Chicago to Oakland with Cheapflights

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Cheapflights Tip: The best prices from Chicago to Oakland are usually found in September or July, booked 68 days in advance, depart on a Monday or Wednesday and return on a Wednesday

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 January 29, 2026.

This Southwest deal was found by Cheapflights users on 1/26. 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 2/2511:10 am
MDW
-
OAK
Nonstop4h 55m
Southwest
Wed 3/411:10 am
OAK
-
MDW
Nonstop4h 05m
Southwest
Deal found 1/26$217
This Southwest deal was found by Cheapflights users on 1/28. 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 3/35:35 pm
MDW
-
OAK
1 stop6h 40m
Southwest
Tue 3/315:50 am
OAK
-
MDW
Nonstop4h 05m
Southwest
Deal found 1/28$227
This CheapOair deal was found by Cheapflights users on 1/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/242:07 pm
ORD
-
OAK
1 stop21h 17m
Alaska Airlines
Sat 2/286:15 am
OAK
-
ORD
1 stop8h 18m
Alaska Airlines
Deal found 1/28$237
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/253:54 pm
ORD
-
OAK
1 stop8h 55m
Hawaiian Airlines
Mon 3/26:15 am
OAK
-
ORD
1 stop15h 41m
Hawaiian Airlines
Deal found 1/28$240
This Delta deal was found by Cheapflights users on 1/28. 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 3/178:55 am
ORD
-
OAK
2 stops9h 05m
Delta
Tue 3/2412:35 pm
OAK
-
ORD
1 stop6h 59m
Delta
Deal found 1/28$242
This Alaska Airlines deal was found by Cheapflights users on 1/28. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/28:50 am
ORD
-
OAK
1 stop11h 25m
Alaska Airlines
Tue 5/123:18 pm
OAK
-
ORD
1 stop25h 28m
Alaska Airlines
Deal found 1/28$243
This Southwest deal was found by Cheapflights users on 1/28. 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 3/59:30 pm
MDW
-
OAK
Nonstop4h 40m
Southwest
Tue 3/3111:55 pm
OAK
-
MDW
Nonstop4h 00m
Southwest
Deal found 1/28$250
This CheapOair deal was found by Cheapflights users on 1/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/288:50 am
ORD
-
OAK
1 stop27h 27m
Alaska Airlines
Sat 5/22:09 pm
OAK
-
ORD
1 stop7h 50m
Alaska Airlines
Deal found 1/28$250
This Alaska Airlines deal was found by Cheapflights users on 1/28. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/87:59 pm
ORD
-
OAK
1 stop24h 16m
Alaska Airlines
Tue 5/197:00 am
OAK
-
ORD
1 stop9h 46m
Alaska Airlines
Deal found 1/28$253
This CheapOair deal was found by Cheapflights users on 1/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/212:07 pm
ORD
-
OAK
1 stop21h 17m
Alaska Airlines
Sat 2/286:15 am
OAK
-
ORD
1 stop8h 18m
Alaska Airlines
Deal found 1/28$255
This Southwest deal was found by Cheapflights users on 1/28. 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.
Sat 2/218:05 am
MDW
-
OAK
1 stop7h 55m
Southwest
Wed 2/2511:10 am
OAK
-
MDW
Nonstop4h 05m
Southwest
Deal found 1/28$257
This Alaska Airlines deal was found by Cheapflights users on 1/27. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/253:54 pm
ORD
-
OAK
1 stop8h 55m
Alaska Airlines
Sat 2/286:15 am
OAK
-
ORD
1 stop8h 18m
Alaska Airlines
Deal found 1/27$257

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$217
(Southwest)

One-way from

$109
(Southwest)

Popular in

November

Cheapest in

September

Average price

$591

Good round-trip deal

$289 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. 25% potential increase in price ($139 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($28 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 29, 2026.
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

MDW - OAK

MDWOAK

Chicago Midway

Tue 3/3

5:35 pm-10:15 pm

1 stop6h 40m

Oakland

Tue 3/31

5:50 am-11:55 am

Nonstop4h 05m

$227

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Wed 2/25

3:54 pm-10:49 pm

1 stop8h 55m

Oakland

Sat 2/28

6:15 am-4:33 pm

1 stop8h 18m

$237

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Thu 3/5

9:30 pm-12:10 am

Nonstop4h 40m

Oakland

Tue 3/31

11:55 pm-5:55 am

Nonstop4h 00m

$250

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Tue 3/17

9:00 pm-11:40 pm

Nonstop4h 40m

Oakland

Tue 3/24

11:55 pm-5:55 am

Nonstop4h 00m

$257

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Wed 3/25

6:00 am-11:43 pm

1 stop19h 43m

Oakland

Tue 4/7

6:40 pm-6:39 am

1 stop9h 59m

$260

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Wed 3/11

4:15 pm-9:45 pm

1 stop7h 30m

Oakland

Tue 3/17

6:15 am-6:50 pm

2 stops10h 35m

$272

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Mon 4/6

9:30 pm-12:10 am

Nonstop4h 40m

Oakland

Tue 4/14

11:55 pm-6:00 am

Nonstop4h 05m

$272

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Wed 2/25

8:10 am-2:55 pm

2 stops8h 45m

Oakland

Wed 3/4

9:40 am-7:55 pm

1 stop8h 15m

$273

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Tue 3/3

7:15 am-11:55 am

1 stop6h 40m

Oakland

Thu 3/5

5:55 am-6:01 pm

2 stops10h 06m

$275

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Tue 2/17

6:45 pm-11:51 pm

1 stop7h 06m

Oakland

Thu 2/19

12:40 pm-9:52 pm

1 stop7h 12m

$301

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/29

Showing 1-10 of 37 results
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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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Oakland, California flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 January 23, 2026.

To ensure you get the cheapest price possible for a flight from Chicago to Oakland, California, you should look to book at least 68 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 January 29, 2026.

It’s typically best to fly out from Chicago to Oakland, California in the evening. Doing so could potentially save you 50% on the flight price compared to flying in the morning, which is usually more expensive.

How often are flights from Chicago to Oakland delayed?

About 24% of weekly flights between Chicago and Oakland have experienced delays in the past year, with the average delay time being 97 minutes.

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

Historically, flights departing in the early afternoon 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?

Friday 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 28% 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
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

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 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 January 29, 2026.
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
8.0
Very good
4,267 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

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
8.0
Very good
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

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
8,127 reviews
Southwest
8.0
Very good
4,267 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

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
9,214 reviews
Southwest
8.0
Very good
4,267 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

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
8,389 reviews
Southwest
8.0
Very good
4,267 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

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 40m. Southwest provides one of the quickest options available for as low as $227. The distance between Chicago and Oakland, California is about 1839 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

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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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$53Average$229FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$236Average$414FlexibilityNo cancel feeOn-time63%

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