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Oakland

$116+ 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 2/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OAK
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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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 Thursday and return on a Sunday

Find 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 October 30, 2025.

This Delta deal was found by Cheapflights users on 10/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/37:40 pmORD - OAK
1 stop6h 28mDelta
Mon 12/812:30 pmOAK - ORD
1 stop6h 51mDelta
Deal found 10/27$261
This KAYAK deal was found by Cheapflights users on 10/29. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/86:00 amORD - OAK
1 stop9h 32mAlaska Airlines
Thu 12/116:40 amOAK - ORD
1 stop8h 15mAlaska Airlines
Deal found 10/29$282
This Delta deal was found by Cheapflights users on 10/28. 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.
Thu 11/2710:10 amORD - OAK
2 stops10h 03mDelta
Wed 12/312:30 pmOAK - ORD
1 stop6h 51mDelta
Deal found 10/28$290
This Delta deal was found by Cheapflights users on 10/28. 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.
Thu 11/2710:10 amORD - OAK
2 stops10h 03mDelta
Sat 12/612:30 pmOAK - ORD
1 stop6h 51mDelta
Deal found 10/28$291
This Alaska Airlines deal was found by Cheapflights users on 10/28. 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.
Wed 11/198:00 amORD - OAK
1 stop17h 59mAlaska Airlines
Wed 12/32:31 pmOAK - ORD
1 stop7h 28mAlaska Airlines
Deal found 10/28$292
This Delta deal was found by Cheapflights users on 10/28. 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.
Thu 11/2710:10 amORD - OAK
2 stops10h 03mDelta
Thu 12/45:55 amOAK - ORD
2 stops12h 00mDelta
Deal found 10/28$295
This Southwest deal was found by Cheapflights users on 10/28. 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 11/277:15 amORD - OAK
1 stop8h 20mSouthwest
Tue 12/25:25 amOAK - ORD
1 stop6h 05mSouthwest
Deal found 10/28$296
This Alaska Airlines deal was found by Cheapflights users on 10/29. 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 11/198:00 amORD - OAK
1 stop7h 55mAlaska Airlines
Tue 12/166:40 amOAK - ORD
2 stops15h 10mAlaska Airlines
Deal found 10/29$298
This Southwest deal was found by Cheapflights users on 10/29. 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 12/62:05 pmMDW - OAK
Nonstop4h 40mSouthwest
Tue 12/911:00 amOAK - MDW
Nonstop4h 05mSouthwest
Deal found 10/29$298
This Delta deal was found by Cheapflights users on 10/28. 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.
Thu 11/2710:10 amORD - OAK
2 stops10h 03mDelta
Fri 12/512:30 pmOAK - ORD
1 stop6h 51mDelta
Deal found 10/28$301
This Alaska Airlines deal was found by Cheapflights users on 10/28. 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.
Tue 11/188:00 amORD - OAK
1 stop7h 55mAlaska Airlines
Tue 12/26:40 amOAK - ORD
1 stop15h 19mAlaska Airlines
Deal found 10/28$302
This Alaska Airlines deal was found by Cheapflights users on 10/29. 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 11/192:05 pmORD - OAK
2 stops11h 54mAlaska Airlines
Wed 12/176:40 amOAK - ORD
2 stops15h 10mAlaska Airlines
Deal found 10/29$303

Cheap 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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$282
(KAYAK)

One-way from

$116
(Kiwi.com)

Popular in

October

Cheapest in

September

Average price

$497

Good round-trip deal

$336 or less

Good one-way deal

$306 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. 10% potential increase in price ($43 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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 October 30, 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 12/3

7:40 pm-12:08 am

1 stop6h 28m

Oakland

Mon 12/8

12:30 pm-9:21 pm

1 stop6h 51m

$261

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Mon 3/2

7:45 am-5:43 pm

1 stop11h 58m

Oakland

Wed 3/4

6:30 am-5:04 am

1 stop20h 34m

$283

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Tue 3/10

7:45 am-11:38 pm

1 stop17h 53m

Oakland

Wed 3/11

6:30 am-5:04 am

1 stop20h 34m

$283

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Mon 2/2

11:10 am-2:05 pm

Nonstop4h 55m

Oakland

Wed 2/4

11:10 am-5:15 pm

Nonstop4h 05m

$297

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Wed 11/19

8:00 am-1:55 pm

1 stop7h 55m

Oakland

Tue 12/16

6:40 am-11:50 pm

2 stops15h 10m

$298

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Thu 11/27

10:10 am-6:13 pm

2 stops10h 03m

Oakland

Fri 12/5

12:30 pm-9:21 pm

1 stop6h 51m

$301

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Thu 12/11

5:51 pm-11:59 pm

1 stop8h 08m

Oakland

Sat 12/13

2:31 pm-11:59 pm

1 stop7h 28m

$302

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Wed 11/19

2:05 pm-11:59 pm

2 stops11h 54m

Oakland

Wed 12/17

6:40 am-11:50 pm

2 stops15h 10m

$303

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Wed 11/19

2:05 pm-11:59 pm

2 stops11h 54m

Oakland

Tue 12/2

6:40 am-11:59 pm

1 stop15h 19m

$308

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Mon 2/2

1:28 pm-11:53 pm

2 stops12h 25m

Oakland

Wed 2/4

5:55 am-5:55 pm

2 stops10h 00m

$312

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 39 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 October.
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 October 24, 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 June is currently the most expensive (average of $198). 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 October 30, 2025.

It’s typically best to fly out from Chicago to Oakland, California in the afternoon. Doing so could potentially save you 30% 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 October 26, 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.

How much does it cost to fly round-trip from Chicago to Oakland, California?

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 67% 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: 8h 30m.

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 2h 45m.

The best insider tips for Chicago to Oakland flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
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 October 30, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest, 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.
Alaska Airlines
8.0
Very good
11,219 reviews

Overall

8.0

Boarding

8.1

Food

7.1

Crew

8.5

Entertainment

7.0

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Alaska Airlines
8.0
Very good
11,219 reviews
Alaska Airlines
8.0
Very good
11,219 reviews

Overall

8.0

Boarding

8.1

Food

7.1

Crew

8.5

Entertainment

7.0

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Southwest
8.0
Very good
4,243 reviews
Alaska Airlines
8.0
Very good
11,219 reviews

Overall

8.0

Boarding

8.1

Food

7.1

Crew

8.5

Entertainment

7.0

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
United Airlines
7.4
Good
8,998 reviews
Alaska Airlines
8.0
Very good
11,219 reviews

Overall

8.0

Boarding

8.1

Food

7.1

Crew

8.5

Entertainment

7.0

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Spirit Airlines
6.3
Okay
8,116 reviews
Alaska Airlines
8.0
Very good
11,219 reviews

Overall

8.0

Boarding

8.1

Food

7.1

Crew

8.5

Entertainment

7.0

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.

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 4h 55m. Delta provides one of the quickest options available for as low as $297. 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 $83 on this airline. An additional option worth looking into is Southwest, starting at $245. These flights start at 77% 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 Delta, with whom users have recently found tickets for as low as $131. However, be on the lookout for offers from Alaska Airlines and Southwest, 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 June is currently the most expensive (average of $198). 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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Alternative routes for Chicago to Oakland

See prices for flight routes from nearby airports that may be better suited for you.
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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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$83Average$234FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$245Average$440FlexibilityNo cancel feeOn-time63%

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