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Oakland

$84+ 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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OAK
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
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

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 September 15, 2025.

Round-trip from

$197
(CheapOair)

One-way from

$84
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$253

Good round-trip deal

$448 or less

Good one-way deal

$238 or less
From Chicago (CHI) to Oakland
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One-way flight from Chicago (CHI) to Oakland
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Highest demand for flights based on searches. 8% potential increase in price ($34 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Oakland.
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Price to beat on a one-way flight from Chicago (CHI) to Oakland.
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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 September 15, 2025.

This CheapOair deal was found by Cheapflights users on 9/14. 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.
Mon 9/296:05 pmORD - OAK
1 stop7h 27mSpirit Airlines
Fri 10/310:56 amOAK - ORD
2 stops8h 40mSpirit Airlines
Deal found 9/14$197
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/3011:15 amORD - OAK
1 stop14h 17mSpirit Airlines
Wed 10/16:30 amOAK - ORD
1 stop13h 02mSpirit Airlines
Deal found 9/15$225
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/296:05 pmORD - OAK
1 stop7h 27mSpirit Airlines
Wed 10/16:30 amOAK - ORD
1 stop13h 02mSpirit Airlines
Deal found 9/15$231
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/111:15 amORD - OAK
1 stop14h 17mMultiple Airlines
Wed 10/87:06 pmOAK - ORD
1 stop7h 55mMultiple Airlines
Deal found 9/14$233
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Tue 9/3011:15 amORD - OAK
1 stop14h 17mMultiple Airlines
Sat 10/410:56 amOAK - ORD
2 stops44h 41mMultiple Airlines
Deal found 9/14$236
This KAYAK deal was found by Cheapflights users on 9/14. 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.
Sat 10/255:59 pmORD - OAK
1 stop8h 04mAlaska Airlines
Wed 10/292:49 pmOAK - ORD
1 stop7h 35mAlaska Airlines
Deal found 9/14$261
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Sun 9/288:49 pmORD - OAK
2 stops28h 43mMultiple Airlines
Thu 10/26:30 amOAK - ORD
1 stop27h 21mMultiple Airlines
Deal found 9/14$262
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/255:59 pmORD - OAK
1 stop8h 04mAlaska Airlines
Thu 10/302:49 pmOAK - ORD
1 stop7h 35mAlaska Airlines
Deal found 9/15$272
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/229:54 pmORD - OAK
2 stops38h 07mMultiple Airlines
Thu 9/256:30 amOAK - ORD
1 stop27h 21mMultiple Airlines
Deal found 9/15$273
This Southwest deal was found by Cheapflights users on 9/15. 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.
Wed 10/157:10 amMDW - OAK
1 stop7h 40mSouthwest
Wed 10/223:10 pmOAK - MDW
1 stop7h 15mSouthwest
Deal found 9/15$297
This Southwest deal was found by Cheapflights users on 9/15. 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 10/289:20 amMDW - OAK
2 stops7h 55mSouthwest
Tue 11/47:50 amOAK - MDW
1 stop7h 05mSouthwest
Deal found 9/15$302
This Southwest deal was found by Cheapflights users on 9/14. 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 10/2310:35 amMDW - OAK
1 stop7h 10mSouthwest
Mon 10/275:50 amOAK - MDW
Nonstop4h 05mSouthwest
Deal found 9/14$307

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 September 15, 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

Fri 10/24

3:15 pm-12:03 am

1 stop10h 48m

Oakland

Mon 10/27

8:03 pm-6:22 am

1 stop8h 19m

$276

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Mon 10/27

6:00 am-1:55 pm

1 stop9h 55m

Oakland

Thu 10/30

2:49 pm-12:24 am

1 stop7h 35m

$276

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Fri 11/14

2:05 pm-7:23 pm

1 stop7h 18m

Oakland

Sat 11/15

6:30 am-4:57 pm

1 stop8h 27m

$276

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Tue 3/10

2:05 pm-7:14 pm

1 stop7h 09m

Oakland

Wed 3/11

6:35 pm-5:04 am

1 stop8h 29m

$277

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Tue 10/28

1:15 pm-5:45 pm

1 stop6h 30m

Oakland

Tue 11/4

7:50 am-4:55 pm

1 stop7h 05m

$297

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Fri 11/14

3:25 pm-11:59 pm

1 stop10h 34m

Oakland

Sat 11/15

9:48 am-11:59 pm

2 stops12h 11m

$302

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Thu 10/23

10:35 am-3:45 pm

1 stop7h 10m

Oakland

Mon 10/27

5:50 am-11:55 am

Nonstop4h 05m

$307

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Wed 10/1

6:20 am-1:36 pm

1 stop9h 16m

Oakland

Wed 10/8

7:06 pm-5:01 am

1 stop7h 55m

$317

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Mon 11/10

7:00 am-7:23 pm

1 stop14h 23m

Oakland

Wed 11/12

6:30 am-4:30 pm

1 stop8h 00m

$337

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Sat 10/18

5:15 am-12:05 pm

2 stops8h 50m

Oakland

Sun 10/19

6:40 am-12:45 pm

Nonstop4h 05m

$338

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 37 results
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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

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 September 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, April is the cheapest month in which you can book a flight from Chicago to Oakland, California (average of $183). Flying from Chicago to Oakland, California in November is currently the most expensive (average of $259). 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 September 15, 2025.

It’s typically best to fly out from Chicago to Oakland, California at noon. Doing so could potentially save you 39% 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 September 14, 2025.

Travelers seeking maximum savings on their Chicago to Oakland, California flight should consider departing on Wednesday at noon when fares are most often at their lowest. Sunday mornings 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 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.

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 September 15, 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
10,000 reviews

Comfort

7.8

Food

7.1

Overall

8.0

Boarding

8.1

Crew

8.5

Entertainment

7.0

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
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Food

7.1

Overall

8.0

Boarding

8.1

Crew

8.5

Entertainment

7.0

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
4,242 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Food

7.1

Overall

8.0

Boarding

8.1

Crew

8.5

Entertainment

7.0

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
8,929 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Food

7.1

Overall

8.0

Boarding

8.1

Crew

8.5

Entertainment

7.0

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
8,015 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Food

7.1

Overall

8.0

Boarding

8.1

Crew

8.5

Entertainment

7.0

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 2 daily inbound flights from Chicago from 3 different airlines.

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

    A quick flight from Chicago to Oakland, California can take about 6h 30m. Hawaiian Airlines 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. Additional options worth looking into are United Airlines and Southwest, starting at $236 and $242 round-trip. These flights start at 76% 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 $138. However, be on the lookout for offers from Hawaiian Airlines 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, April is the cheapest month in which you can book a flight from Chicago to Oakland, California (average of $183). Flying from Chicago to Oakland, California in November is currently the most expensive (average of $259). 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 3 airlines flying from Chicago to Oakland

Discover the top 3 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$83Average$229FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$236Average$357FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$242Average$401FlexibilityNo cancel feeOn-time63%

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