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Oakland

$66+ 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 6/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OAK
may. 6 — may. 131
mar. 5/6
mar. 5/13
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Oakland are usually found in July or September, booked 86 days in advance, depart on a Thursday or Monday 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 mayo 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$136
(Cheapflightsfares)

One-way from

$66
(FlightHub)

Popular in

December

Cheapest in

July

Average price

$322

Good round-trip deal

$287 or less

Good one-way deal

$166 or less
Provider with most accurate pricing for Chicago (CHI)-Oakland flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Oakland flights.
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From Chicago (CHI) to Oakland
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One-way flight from Chicago (CHI) to Oakland
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($32 potential increase over avg. RT price).
Search Deals
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 May 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 mayo 1, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 6/311:50 amORD - OAK
1 stop10h 24mSpirit Airlines
lun. 6/99:09 pmOAK - ORD
1 stop11h 46mSpirit Airlines
Deal found 4/29$136
This Alaska Airlines deal was found by Cheapflights users on 4/29. 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.
mié. 5/288:00 amORD - OAK
1 stop7h 36mAlaska Airlines
sáb. 5/3112:48 pmOAK - ORD
1 stop9h 11mAlaska Airlines
Deal found 4/29$206
This Orbitz deal was found by Cheapflights users on 4/29. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/296:00 amORD - OAK
1 stop8h 08mMultiple Airlines
jue. 6/59:09 pmOAK - ORD
1 stop6h 16mMultiple Airlines
Deal found 4/29$234
This Southwest deal was found by Cheapflights users on 4/29. 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.
mié. 6/48:35 amMDW - OAK
1 stop6h 25mSouthwest
mar. 6/104:25 pmOAK - MDW
1 stop6h 25mSouthwest
Deal found 4/29$247
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 6/57:15 pmORD - OAK
1 stop6h 34mDelta
mié. 6/1112:30 pmOAK - ORD
1 stop7h 39mDelta
Deal found 4/29$257
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 5/301:55 pmMDW - OAK
2 stops11h 54mDelta
lun. 6/26:00 amOAK - MDW
2 stops9h 45mDelta
Deal found 4/29$267

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 mayo 1, 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

mar. 6/3

11:50 am-8:14 pm

1 stop10h 24m

Oakland

lun. 6/9

9:09 pm-10:55 am

1 stop11h 46m

$136

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

mié. 5/28

8:00 am-1:36 pm

1 stop7h 36m

Oakland

sáb. 5/31

12:48 pm-11:59 pm

1 stop9h 11m

$206

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

jue. 5/29

6:00 am-12:08 pm

1 stop8h 08m

Oakland

jue. 6/5

9:09 pm-5:25 am

1 stop6h 16m

$234

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

mié. 6/4

8:35 am-1:00 pm

1 stop6h 25m

Oakland

mar. 6/10

4:25 pm-12:50 am

1 stop6h 25m

$247

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

jue. 6/5

7:15 pm-11:49 pm

1 stop6h 34m

Oakland

mar. 6/10

12:30 pm-10:09 pm

1 stop7h 39m

$257

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

vie. 5/30

1:55 pm-11:49 pm

2 stops11h 54m

Oakland

lun. 6/2

6:00 am-5:45 pm

2 stops9h 45m

$267

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

mar. 6/3

11:50 am-8:14 pm

1 stop10h 24m

$66

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

mié. 7/2

6:15 am-11:45 am

1 stop7h 30m

$100

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

vie. 7/4

2:45 pm-7:05 pm

1 stop6h 20m

$100

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

lun. 6/2

6:25 am-10:25 pm

1 stop18h 00m

$101

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 16 results
1
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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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy2 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 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 April 25, 2025.

To ensure you get the cheapest price possible for a flight from Chicago to Oakland, California, you should look to book at least 85 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 mayo 1, 2025.

It’s typically best to fly out from Chicago to Oakland, California at noon. Doing so could potentially save you 35% 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 March 30, 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 mayo 1, 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
9,968 reviews

Entertainment

7.1

Crew

8.5

Boarding

8.2

Overall

8.0

Comfort

7.9

Food

7.1

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
9,968 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Entertainment

7.1

Crew

8.5

Boarding

8.2

Overall

8.0

Comfort

7.9

Food

7.1

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
4,294 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Entertainment

7.1

Crew

8.5

Boarding

8.2

Overall

8.0

Comfort

7.9

Food

7.1

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
7,934 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Entertainment

7.1

Crew

8.5

Boarding

8.2

Overall

8.0

Comfort

7.9

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.9
Good
2,408 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Entertainment

7.1

Crew

8.5

Boarding

8.2

Overall

8.0

Comfort

7.9

Food

7.1

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
346 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Entertainment

7.1

Crew

8.5

Boarding

8.2

Overall

8.0

Comfort

7.9

Food

7.1

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 are 2 daily inbound flights from Chicago from 4 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 $136 on this airline. Additional options worth looking into are Alaska Airlines and Southwest, starting at $206 and $252 round-trip. These flights start at 60% 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 $66. However, be on the lookout for offers from Southwest and Hawaiian Airlines, 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 4 airlines flying from Chicago to Oakland

Discover the top 4 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 mayo 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$129Average$242FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$238Average$362FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$247Average$390FlexibilityNo cancel feeOn-time63%
DeltaCheapest$256Average$416FlexibilityNo cancel feeOn-timeN/A

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