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$65+ 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 2/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OAK
Jan 21 — Jan 281
Tue 1/21
Tue 1/28
1 adult, Economy
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The best prices from Chicago to Oakland are usually found in July or February, booked 28 days in advance, depart on a Wednesday or Tuesday and return on a Wednesday

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 January 16, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$128
(Booking.com)

One-way from

$65
(FlightHub)

Popular in

March

Cheapest in

July

Average price

$349
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
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High demand for flights, 2% potential price rise
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Best time to find cheap flights, 3% potential price drop
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Average for round-trip flights in January 2025
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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 January 16, 2025.

This Booking.com deal was found by Cheapflights users on 1/16. 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.
Wed 2/1210:45 pmORD - OAK
2 stops18h 34mSpirit Airlines
Wed 2/265:10 amOAK - ORD
1 stop14h 40mSpirit Airlines
Deal found 1/16$128
This Southwest deal was found by Cheapflights users on 1/16. 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 2/155:10 pmMDW - OAK
Nonstop4h 50mSouthwest
Fri 2/216:10 amOAK - MDW
Nonstop4h 05mSouthwest
Deal found 1/16$237
This Delta deal was found by Cheapflights users on 1/16. 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 8/211:16 pmORD - OAK
1 stop10h 16mDelta
Mon 8/2510:45 pmOAK - ORD
1 stop7h 47mDelta
Deal found 1/16$257
This Alaska Airlines deal was found by Cheapflights users on 1/15. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/56:55 pmORD - OAK
1 stop15h 54mAlaska Airlines
Tue 2/1110:41 amOAK - ORD
2 stops11h 18mAlaska Airlines
Deal found 1/15$270
This Delta deal was found by Cheapflights users on 1/16. 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.
Fri 7/251:00 pmMDW - OAK
2 stops10h 32mDelta
Fri 8/110:45 pmOAK - MDW
2 stops11h 45mDelta
Deal found 1/16$298
This Southwest deal was found by Cheapflights users on 1/16. 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 2/156:30 amORD - OAK
1 stop7h 40mSouthwest
Fri 2/215:20 amOAK - ORD
1 stop7h 05mSouthwest
Deal found 1/16$302
This Kissandfly.com deal was found by Cheapflights users on 1/16. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/156:40 amMDW - OAK
2 stops19h 03mMultiple Airlines
Fri 2/216:49 amOAK - MDW
2 stops15h 28mMultiple Airlines
Deal found 1/16$341

Find flights from Chicago to Oakland within your budget

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 16, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Wed 2/12

10:45 pm-3:19 pm

2 stops18h 34m

Oakland

Wed 2/26

12:40 pm-9:50 pm

1 stop7h 10m

$128

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Sat 2/15

5:10 pm-8:00 pm

Nonstop4h 50m

Oakland

Fri 2/21

6:10 am-12:15 pm

Nonstop4h 05m

$237

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Tue 4/1

5:00 pm-11:57 pm

2 stops8h 57m

Oakland

Tue 4/8

12:54 pm-9:59 pm

1 stop7h 05m

$293

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Sat 2/15

6:30 am-12:10 pm

1 stop7h 40m

Oakland

Fri 2/21

5:20 am-2:25 pm

1 stop7h 05m

$302

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Wed 2/12

6:55 pm-8:44 am

1 stop15h 49m

Oakland

Wed 2/19

8:32 pm-4:58 pm

2 stops18h 26m

$315

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Sun 2/16

11:45 am-12:17 am

3 stops14h 32m

Oakland

Sat 2/22

5:10 am-5:28 am

3 stops22h 18m

$322

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Sat 2/15

6:40 am-11:43 pm

2 stops19h 03m

Oakland

Fri 2/21

6:49 am-12:17 am

2 stops15h 28m

$341

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Wed 2/5

10:57 am-11:56 pm

2 stops14h 59m

Oakland

Tue 2/11

6:00 am-5:43 pm

2 stops9h 43m

$378

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Wed 2/19

1:32 pm-10:12 pm

1 stop10h 40m

$65

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Fri 2/28

6:20 pm-9:15 pm

Nonstop4h 55m

$109

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/16

Showing 1-10 of 16 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
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 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.

Travel insights for flights from Chicago to Oakland

Get recent, data-driven insights about flights from Chicago to Oakland including ideal travel times, pricing trends, and more.

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 10, 2025.

To ensure you get the cheapest price possible for a flight from Chicago to Oakland, California, you should look to book at least 28 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 January 16, 2025.

It’s typically best to fly out from Chicago to Oakland, California in the afternoon. Doing so could potentially save you 25% on the flight price compared to flying in the evening, which is usually more expensive.

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 January 16, 2025.
Peruse reviews from past customers who have flown with Southwest, Alaska Airlines and Spirit Airlines 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.
Southwest
8.1
Very good
4,659 reviews

Comfort

8.1

Crew

8.7

Food

7.2

Boarding

8.2

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Southwest
8.1
Very good
4,659 reviews
Southwest
8.1
Very good
4,659 reviews

Comfort

8.1

Crew

8.7

Food

7.2

Boarding

8.2

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Alaska Airlines
8.0
Very good
9,681 reviews
Southwest
8.1
Very good
4,659 reviews

Comfort

8.1

Crew

8.7

Food

7.2

Boarding

8.2

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Delta
8.0
Very good
8,511 reviews
Southwest
8.1
Very good
4,659 reviews

Comfort

8.1

Crew

8.7

Food

7.2

Boarding

8.2

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Spirit Airlines
6.3
Okay
8,098 reviews
Southwest
8.1
Very good
4,659 reviews

Comfort

8.1

Crew

8.7

Food

7.2

Boarding

8.2

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

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 $128 on this airline. Additional options worth looking into are Southwest and Alaska Airlines, starting at $237 and $304 round-trip. These flights start at 62% 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 $65. 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, 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