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Oakland

$71+ 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 8/22. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OAK
jun. 17 — jun. 241
mar. 6/17
mar. 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Oakland are usually found in July or May, booked 68 days in advance, depart on a Monday or Thursday and return on a Monday

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 junio 12, 2025.

Round-trip from

$162
(KAYAK)

One-way from

$71
(FlightHub)

Popular in

December

Cheapest in

July

Average price

$382

Good round-trip deal

$342 or less

Good one-way deal

$258 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. 9% potential increase in price ($34 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in June 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 junio 12, 2025.

This KAYAK deal was found by Cheapflights users on 6/12. 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.
jue. 7/107:08 amORD - OAK
1 stop6h 39mSpirit Airlines
lun. 7/146:00 amOAK - ORD
1 stop6h 13mSpirit Airlines
Deal found 6/12$162
This Southwest deal was found by Cheapflights users on 6/11. 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.
jue. 9/1110:50 amMDW - OAK
1 stop6h 15mSouthwest
lun. 9/158:30 pmOAK - MDW
1 stop6h 40mSouthwest
Deal found 6/11$199
This Booking.com deal was found by Cheapflights users on 6/10. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 6/2810:15 pmORD - OAK
2 stops13h 21mMultiple Airlines
jue. 7/311:59 pmOAK - ORD
1 stop10h 52mMultiple Airlines
Deal found 6/10$220
This Alaska Airlines deal was found by Cheapflights users on 6/10. 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.
sáb. 8/306:20 amORD - OAK
1 stop9h 16mAlaska Airlines
mié. 9/37:58 pmOAK - ORD
1 stop9h 05mAlaska Airlines
Deal found 6/10$240
This Delta deal was found by Cheapflights users on 6/11. 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.
lun. 8/256:25 pmORD - OAK
1 stop6h 21mDelta
sáb. 8/3012:35 pmOAK - ORD
1 stop7h 29mDelta
Deal found 6/11$257
This Southwest deal was found by Cheapflights users on 6/10. 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.
jue. 7/36:15 amORD - OAK
1 stop8h 00mSouthwest
dom. 7/65:30 amOAK - ORD
1 stop8h 55mSouthwest
Deal found 6/10$282
This Delta deal was found by Cheapflights users on 6/10. 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.
mar. 7/19:24 amMDW - OAK
2 stops8h 52mDelta
mar. 7/84:55 pmOAK - MDW
2 stops13h 49mDelta
Deal found 6/10$308
This Mytrip deal was found by Cheapflights users on 6/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 7/1011:37 amMDW - OAK
3 stops22h 51mMultiple Airlines
dom. 7/136:00 amOAK - MDW
2 stops25h 41mMultiple Airlines
Deal found 6/10$491

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 junio 12, 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

jue. 7/10

7:08 am-11:47 am

1 stop6h 39m

Oakland

lun. 7/14

6:00 am-2:13 pm

1 stop6h 13m

$162

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

sáb. 6/28

10:15 pm-9:36 am

2 stops13h 21m

Oakland

jue. 7/3

11:59 pm-12:51 pm

1 stop10h 52m

$220

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

jue. 7/3

7:20 am-9:50 am

Nonstop4h 30m

Oakland

lun. 7/7

9:15 pm-5:00 am

1 stop5h 45m

$227

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

sáb. 8/30

6:20 am-1:36 pm

1 stop9h 16m

Oakland

mié. 9/3

7:58 pm-7:03 am

1 stop9h 05m

$240

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

lun. 8/25

6:25 pm-10:46 pm

1 stop6h 21m

Oakland

sáb. 8/30

12:35 pm-10:04 pm

1 stop7h 29m

$257

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

jue. 7/3

6:15 am-12:15 pm

1 stop8h 00m

Oakland

dom. 7/6

5:30 am-4:25 pm

1 stop8h 55m

$282

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

mar. 7/1

9:24 am-4:16 pm

2 stops8h 52m

Oakland

mar. 7/8

4:55 pm-8:44 am

2 stops13h 49m

$308

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

jue. 7/10

11:37 am-8:28 am

3 stops22h 51m

Oakland

dom. 7/13

6:00 am-9:41 am

2 stops25h 41m

$491

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

vie. 8/22

6:21 pm-7:18 am

1 stop14h 57m

$71

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

sáb. 8/23

10:55 am-3:10 pm

1 stop6h 15m

$95

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/12

Showing 1-10 of 16 results
1
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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 June 9, 2025.

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, 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 junio 12, 2025.

It’s typically best to fly out from Chicago to Oakland, California at noon. Doing so could potentially save you 38% 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 June 8, 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. Wednesday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Rainfall in Oakland by month

Plan your trip to Oakland by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Oakland, California ranges from 0.0 - 4.8 inches per month. January is typically the wettest month, when rainfall can reach 4.8 in. July is typically the driest time to visit Oakland, California when rainfall is around 0.0 in.

Temperature in Oakland by month

Plan your trip to Oakland by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Oakland, California, use this chart to help with planning. For those seeking warmer temperatures, August is the ideal time of year to visit, when temperatures reach an average of 66.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 51.8 F).

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 junio 12, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest and Delta from Chicago to Oakland to help guide your decision. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,946 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Sun Country Air
6.9
Okay
345 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Spirit Airlines
6.3
Okay
8,052 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 is 1 daily inbound flight from Chicago from 5 different airlines.

  • 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 $162 on this airline. Additional options worth looking into are Southwest and Alaska Airlines, starting at $227 and $240 round-trip. These flights start at 53% 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 Spirit Airlines, with whom users have recently found tickets for as low as $71. However, be on the lookout for offers from Southwest and Sun Country Air, 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 5 airlines flying from Chicago to Oakland

Discover the top 5 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 junio 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$129Average$234FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$238Average$394FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$238Average$362FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$246Average$386FlexibilityNo cancel feeOn-time63%
DeltaCheapest$256Average$416FlexibilityNo cancel feeOn-timeN/A

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