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Oakland

$47+ 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 12/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OAK
nov. 26 — dic. 31
mar. 11/26
mar. 12/3
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 Thursday 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 noviembre 21, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

March

Cheapest in

July

Round-trip from

$235
(CheapOair)

One-way from

$47
(Cheapflightsfares)
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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High demand for flights, 26% potential price rise
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Best time to find cheap flights, 26% potential price drop
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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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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 noviembre 21, 2024.

This Cheapflightsfares deal was found by Cheapflights users on 11/20. 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.
vie. 12/209:54 pmORD - OAK
1 stop13h 49mSpirit Airlines
mar. 12/249:25 pmOAK - ORD
1 stop6h 05mSpirit Airlines
Deal found 11/20$235
This Delta deal was found by Cheapflights users on 11/20. 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.
mié. 12/187:10 pmORD - OAK
1 stop7h 05mDelta
mié. 12/255:30 amOAK - ORD
1 stop6h 21mDelta
Deal found 11/20$317
This Southwest deal was found by Cheapflights users on 11/20. 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. 12/115:10 pmMDW - OAK
Nonstop4h 45mSouthwest
dom. 12/154:50 pmOAK - MDW
1 stop6h 00mSouthwest
Deal found 11/20$318
This Alaska Airlines deal was found by Cheapflights users on 11/20. 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. 12/257:00 amORD - OAK
1 stop13h 52mAlaska Airlines
vie. 1/37:32 pmOAK - ORD
1 stop7h 58mAlaska Airlines
Deal found 11/20$359
This Delta deal was found by Cheapflights users on 11/20. 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.
mié. 12/111:30 pmMDW - OAK
2 stops12h 44mDelta
dom. 12/156:00 amOAK - MDW
2 stops9h 01mDelta
Deal found 11/20$415
This Mytrip deal was found by Cheapflights users on 11/19. 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. 11/289:20 amORD - OAK
3 stops15h 52mMultiple Airlines
mar. 12/31:18 pmOAK - ORD
3 stops26h 22mMultiple Airlines
Deal found 11/19$418
This Southwest deal was found by Cheapflights users on 11/20. 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. 12/2512:15 pmORD - OAK
2 stops9h 45mSouthwest
vie. 1/36:30 pmOAK - ORD
2 stops12h 50mSouthwest
Deal found 11/20$431
This Mytrip deal was found by Cheapflights users on 11/21. 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.
mié. 11/277:55 pmMDW - OAK
2 stops20h 30mVolaris
lun. 12/25:59 pmOAK - MDW
1 stop12h 46mVolaris
Deal found 11/21$717
This Mytrip deal was found by Cheapflights users on 11/21. 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.
vie. 11/297:55 pmMDW - OAK
2 stops20h 30mMultiple Airlines
mar. 12/35:30 amOAK - MDW
2 stops25h 15mMultiple Airlines
Deal found 11/21$721

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 2,612,795 searches. Data last updated noviembre 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

jue. 12/5

3:21 pm-11:05 pm

1 stop9h 44m

Oakland

vie. 12/13

3:35 pm-5:30 am

2 stops11h 55m

$235

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

mié. 12/18

7:10 pm-12:15 am

1 stop7h 05m

Oakland

mié. 12/25

5:30 am-1:51 pm

1 stop6h 21m

$317

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

mié. 12/11

5:10 pm-7:55 pm

Nonstop4h 45m

Oakland

dom. 12/15

4:50 pm-12:50 am

1 stop6h 00m

$318

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

sáb. 4/5

2:05 pm-10:33 pm

1 stop10h 28m

Oakland

lun. 4/7

7:30 pm-5:04 am

1 stop7h 34m

$322

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

sáb. 12/21

4:21 pm-3:57 pm

2 stops25h 36m

Oakland

sáb. 12/28

6:36 pm-7:34 pm

3 stops22h 58m

$388

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

mié. 12/11

1:30 pm-12:14 am

2 stops12h 44m

Oakland

dom. 12/15

6:00 am-5:01 pm

2 stops9h 01m

$415

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

mié. 12/25

12:15 pm-8:00 pm

2 stops9h 45m

Oakland

vie. 1/3

6:30 pm-9:20 am

2 stops12h 50m

$431

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

mar. 12/17

9:10 pm-9:43 am

1 stop14h 33m

$47

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

mié. 1/22

7:20 pm-11:56 pm

1 stop6h 36m

$128

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

mar. 1/21

9:40 am-12:35 pm

Nonstop4h 55m

$129

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/21

Showing 1-10 of 17 results
1
2

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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*1 star

*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 November 15, 2024.

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, May is the cheapest month in which you can book a flight from Chicago to Oakland, California (average of $179). Flying from Chicago to Oakland, California in July is currently the most expensive (average of $243). 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 noviembre 21, 2024.

It’s typically best to fly out from Chicago to Oakland, California in the afternoon. Doing so could potentially save you 26% 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 noviembre 21, 2024.
Peruse reviews from past customers who have flown with Spirit Airlines, Delta and Southwest 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
5,005 reviews

Food

7.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

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
5,005 reviews
Southwest
8.1
Very good
5,005 reviews

Food

7.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

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
9,464 reviews
Southwest
8.1
Very good
5,005 reviews

Food

7.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

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
8,755 reviews
Southwest
8.1
Very good
5,005 reviews

Food

7.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

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.

Volaris
6.7
Okay
1,286 reviews
Southwest
8.1
Very good
5,005 reviews

Food

7.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

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
8,169 reviews
Southwest
8.1
Very good
5,005 reviews

Food

7.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

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 is 1 daily inbound flight 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 $235 on this airline. Additional options worth looking into are Delta and Southwest, starting at $317 and $318 round-trip. These flights start at 27% 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 $47. However, be on the lookout for offers from Delta 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, May is the cheapest month in which you can book a flight from Chicago to Oakland, California (average of $179). Flying from Chicago to Oakland, California in July is currently the most expensive (average of $243). 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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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 2,612,795 searches. Data last updated noviembre 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$133Average$246FlexibilityNo cancel feeOn-time65%
DeltaCheapest$235Average$325FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$236Average$396FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$242Average$377FlexibilityNo cancel feeOn-time63%
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