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$41+ Cheap flights from Chicago (CHI) to Oakland (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 11/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OAK
Nov 5 — Nov 121
1 adult
Tue 11/5
Tue 11/12
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The best prices from Chicago to Oakland are usually found in February or July, booked 28 days in advance, depart on a Wednesday or Sunday 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 October 31, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

March

Cheapest in

February

Round-trip from

$192
(FareScan)

One-way from

$53
(CheapOair)
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, 29% potential price rise
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Best time to find cheap flights, 34% 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 October 31, 2024.

This FareScan deal was found by Cheapflights users on 10/30. 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 FareScan is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/238:27 pmORD - OAK
1 stop14h 45mSpirit Airlines
Mon 12/210:07 amOAK - ORD
1 stop23h 45mSpirit Airlines
Deal found 10/30$192
This Delta deal was found by Cheapflights users on 10/30. 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.
Mon 12/163:35 pmORD - OAK
2 stops10h 39mDelta
Sat 1/115:55 amOAK - ORD
1 stop5h 54mDelta
Deal found 10/30$261
This Delta deal was found by Cheapflights users on 10/30. 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 12/129:30 amMDW - OAK
2 stops8h 46mDelta
Mon 12/166:00 amOAK - MDW
2 stops9h 01mDelta
Deal found 10/30$266
This Alaska Airlines deal was found by Cheapflights users on 10/30. 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.
Sat 12/71:07 pmORD - OAK
1 stop9h 45mAlaska Airlines
Mon 12/98:50 amOAK - ORD
2 stops18h 29mAlaska Airlines
Deal found 10/30$271
This Southwest deal was found by Cheapflights users on 10/30. 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.
Mon 12/169:55 amMDW - OAK
1 stop7h 15mSouthwest
Sat 1/117:15 amOAK - MDW
1 stop7h 00mSouthwest
Deal found 10/30$272
This Travelocity deal was found by Cheapflights users on 10/30. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/166:32 amORD - OAK
1 stop10h 28mMultiple Airlines
Sat 1/114:33 pmOAK - ORD
1 stop11h 37mMultiple Airlines
Deal found 10/30$274
This Southwest deal was found by Cheapflights users on 10/30. 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.
Fri 12/204:20 pmORD - OAK
1 stop10h 10mSouthwest
Fri 12/278:40 pmOAK - ORD
1 stop10h 40mSouthwest
Deal found 10/30$341
This Trip.com deal was found by Cheapflights users on 10/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/810:49 pmMDW - OAK
1 stop17h 34mMultiple Airlines
Sun 11/105:30 amOAK - MDW
1 stop14h 34mMultiple Airlines
Deal found 10/30$390
This Frontier deal was found by Cheapflights users on 10/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/57:15 amMDW - OAK
2 stops16h 00mFrontier
Thu 12/125:59 pmOAK - MDW
1 stop12h 31mFrontier
Deal found 10/30$623
This Mytrip deal was found by Cheapflights users on 10/31. 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.
Thu 12/127:55 pmMDW - OAK
2 stops25h 08mVolaris
Sun 12/155:59 pmOAK - MDW
1 stop12h 31mVolaris
Deal found 10/31$903

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 2,570,725 searches. Data last updated October 31, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Wed 11/20

11:17 pm-9:12 am

1 stop11h 55m

$41

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Wed 1/29

9:40 am-12:35 pm

Nonstop4h 55m

$109

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Tue 12/10

7:00 am-3:00 pm

1 stop10h 00m

$118

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Tue 12/17

7:10 pm-12:14 am

1 stop7h 04m

$128

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Fri 12/13

11:55 am-9:25 am

3 stops23h 30m

$185

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Mon 12/9

2:15 pm-12:14 am

2 stops11h 59m

$133

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Mon 3/10

6:40 pm-4:59 pm

3 stops24h 19m

$281

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Sun 1/5

4:20 pm-12:30 am

1 stop10h 10m

$144

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Thu 11/21

11:31 am-9:12 am

3 stops23h 41m

$239

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Thu 3/6

10:41 pm-12:14 pm

1 stop15h 33m

$351

Flights are sorted by cheapest first

Deals found on 10/31

Showing 1-10 of 20 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 October.
ProviderPrice AccuracyTrust Score*Cancellation Policy
ExpediaPrice Accuracy1 starTrust Score*3 starsCancellation PolicyAirline Policy
eDreamsPrice Accuracy3 starsTrust Score*3 starsCancellation PolicyAirline Policy
FlightHubPrice Accuracy3 starsTrust Score*3 starsCancellation PolicyAirline Policy
PricelinePrice Accuracy1 starTrust Score*3 starsCancellation PolicyAirline Policy
CheapflightsfaresPrice Accuracy3 starsTrust Score*1 starCancellation PolicyAirline Policy

*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 October 25, 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.

Find deals

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 $178). Flying from Chicago to Oakland, California in July is currently the most expensive (average of $242). 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 October 31, 2024.

It’s typically best to fly out from Chicago to Oakland, California at noon. Doing so could potentially save you 37% 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 October 31, 2024.
Peruse reviews from past customers who have flown with Southwest, Spirit Airlines and Alaska 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
5,116 reviews

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.1

Crew

8.7

Boarding

8.3

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
5,116 reviews
Southwest
8.1
Very good
5,116 reviews

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.1

Crew

8.7

Boarding

8.3

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
9,420 reviews
Southwest
8.1
Very good
5,116 reviews

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.1

Crew

8.7

Boarding

8.3

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
8,835 reviews
Southwest
8.1
Very good
5,116 reviews

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.1

Crew

8.7

Boarding

8.3

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.

VivaAerobus
6.9
Okay
856 reviews
Southwest
8.1
Very good
5,116 reviews

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.1

Crew

8.7

Boarding

8.3

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
1,316 reviews
Southwest
8.1
Very good
5,116 reviews

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.1

Crew

8.7

Boarding

8.3

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 0 daily inbound flights from Chicago from 4 different airlines.

  • Can I find flights from Chicago to Oakland, California for under $200 on Cheapflights?

    Yes, there are multiple flights from Chicago to Oakland, California for under $200. The cheapest flight booked recently is on Spirit Airlines for just $192, but on average you can expect to pay $370.

  • Are there nonstop flights from Chicago to Oakland, California for under $400 on Cheapflights?

    Cheapflights has at least 1 direct flight from Chicago to Oakland, California under $400. A good price for a nonstop flight from Chicago to Oakland, California is less than $328.

  • Are there last-minute flights available from Chicago to Oakland, California for under $300?

    There are currently 8+ open flights from Chicago to Oakland, California within the next 7 days for less than $300.

  • 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 $192 on this airline. Additional options worth looking into are Alaska Airlines and Delta, starting at $236 and $256 round-trip. These flights start at 38% 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 $53. However, be on the lookout for offers from Southwest and Alaska Airlines, as they are both options that can get you from Chicago to Oakland, California for a low price.

  • What does ORD to OAK mean?

    This is defined as Chicago O'Hare Intl Airport (ORD) and Oakland Airport (OAK). Codes like Oakland Airport are often used to just call airports uniquely. Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD) are some additional IATA codes for airports related to your trip.

  • Can I find deals for flights from Chicago to Oakland that include extra baggage allowance?

    The amount of baggage you can bring on your Chicago to Oakland flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Chicago to Oakland with specific airlines?

    Yes, Cheapflights allows you to browse and filter Chicago to Oakland flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Chicago to Oakland that allow pets onboard?

    Many airlines flying from Chicago to Oakland offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Chicago to Oakland?

    Yes, you can often find last-minute deals on Chicago to Oakland flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago to Oakland, California flight deals updated?

    The Chicago to Oakland, California flight deals you see on this page were last updated on 10/31.

  • 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 $178). Flying from Chicago to Oakland, California in July is currently the most expensive (average of $242). 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 2,570,725 searches. Data last updated October 31, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$129Average$243FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$158Average$396FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$207Average$390FlexibilityNo cancel feeOn-time63%
DeltaCheapest$235Average$276FlexibilityNo cancel feeOn-timeN/A
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