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 $151 on this airline. Additional options worth looking into are Southwest and Delta, starting at $237 and $262 round-trip. These flights start at 55% 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 $76. 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.

What are the most popular airlines that fly from Chicago to Oakland, California?

The most popular airlines flying from Chicago to Oakland, California are Alaska Airlines, Delta and Spirit Airlines. Something to consider prior to booking your flight.

What is the cheapest day to fly round-trip from Chicago to Oakland, California?

Users have found that leaving on a Wednesday can be a cost-effective option. It’s possible to save up to 65% on your flight compared to booking on days when demand is much higher.

How far in advance should I book a flight from Chicago to Oakland, California?

To save up to 95% on this flight, we recommend booking at least 49 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Chicago to Oakland, California from $321 1-2 weeks out and tickets from $479 for flights departing within the next 72 hours.

What is the cheapest month to fly from Chicago to Oakland, California?

Our data shows that September tends to be the cheapest month to fly to Oakland, California from Chicago. Users have commonly found prices around $316 for the month, but tickets can be as low as $119. Due to multiple factors, prepare for potentially higher prices in December.

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.

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.

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.

$76+ Flights from Chicago to Oakland, CA

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Find cheap flights from Chicago to Oakland with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Chicago to Oakland are usually found in July or April, booked 28 days in advance, depart on a Thursday or Monday and return on a Sunday

Cheap flight deals from Chicago to Oakland

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Round-trip from	$151 (Mytrip)
One-way from	$76 (Mytrip)
Popular in	December
Cheapest in	July
Average price	$342
Good round-trip deal	$333 or less
Good one-way deal	$193 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.

Search Deals

From Chicago (CHI) to Oakland

Search Deals

One-way flight from Chicago (CHI) to Oakland

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Highest demand for flights based on searches. 10% potential increase in price ($40 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).

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Average for round-trip flights in March 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 March 28, 2025.

Mon 4/283:08 pmORD - OAK

1 stop28h 27mSpirit Airlines

Wed 4/306:29 pmOAK - ORD

1 stop10h 04mSpirit Airlines

Deal found 3/26

$151

Tue 5/62:07 pmORD - OAK

1 stop7h 08mMultiple Airlines

Tue 5/139:09 pmOAK - ORD

1 stop11h 46mMultiple Airlines

Deal found 3/27

$207

Fri 4/189:10 pmMDW - OAK

Nonstop4h 35mSouthwest

Sun 4/205:55 amOAK - MDW

Nonstop4h 10mSouthwest

Deal found 3/27

$237

Sat 5/37:00 amORD - OAK

1 stop9h 25mSouthwest

Mon 5/53:10 pmOAK - ORD

1 stop5h 55mSouthwest

Deal found 3/26

$252

Fri 4/187:10 pmORD - OAK

1 stop6h 33mDelta

Sun 4/206:00 amOAK - ORD

2 stops9h 04mDelta

Deal found 3/27

$262

Sat 4/191:16 pmMDW - OAK

2 stops11h 10mDelta

Sat 4/266:00 amOAK - MDW

2 stops9h 19mDelta

Deal found 3/27

$267

Sat 10/42:00 pmORD - OAK

1 stop7h 45mAlaska Airlines

Wed 10/82:35 pmOAK - ORD

1 stop7h 24mAlaska Airlines

Deal found 3/26

$275

Sat 4/192:04 pmORD - OAK

1 stop7h 33mHawaiian Airlines

Sat 4/269:15 amOAK - ORD

1 stop7h 01mHawaiian Airlines

Deal found 3/26

$321

Fri 4/1810:59 amMDW - OAK

2 stops26h 54mMultiple Airlines

Sun 4/2012:48 pmOAK - MDW

2 stops19h 21mMultiple Airlines

Deal found 3/27

$358

Best flights from Chicago to Oakland
Discover carefully curated flight deals from Chicago to Oakland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 28, 2025.

Mon 4/283:08 pmORD - OAK

1 stop28h 27mSpirit Airlines

Wed 4/306:29 pmOAK - ORD

1 stop10h 04mSpirit Airlines

Deal found 3/26

$151

Tue 5/62:07 pmORD - OAK

1 stop7h 08mMultiple Airlines

Tue 5/139:09 pmOAK - ORD

1 stop11h 46mMultiple Airlines

Deal found 3/27

$207

Fri 4/189:10 pmMDW - OAK

Nonstop4h 35mSouthwest

Sun 4/205:55 amOAK - MDW

Nonstop4h 10mSouthwest

Deal found 3/27

$237

Fri 4/187:10 pmORD - OAK

1 stop6h 33mDelta

Sun 4/206:00 amOAK - ORD

2 stops9h 04mDelta

Deal found 3/27

$262

Wed 4/95:53 pmORD - OAK

1 stop7h 50mAlaska Airlines

Wed 4/166:43 amOAK - ORD

1 stop9h 12mAlaska Airlines

Deal found 3/26

$276

Sat 4/192:04 pmORD - OAK

1 stop7h 33mHawaiian Airlines

Sat 4/269:15 amOAK - ORD

1 stop7h 01mHawaiian Airlines

Deal found 3/26

$321

Sat 5/37:00 amORD - OAK

1 stop9h 25mSouthwest

Mon 5/53:10 pmOAK - ORD

1 stop5h 55mSouthwest

Deal found 3/26

$252

Sat 4/191:16 pmMDW - OAK

2 stops11h 10mDelta

Sat 4/266:00 amOAK - MDW

2 stops9h 19mDelta

Deal found 3/26

$267

Fri 4/1810:59 amMDW - OAK

2 stops26h 54mMultiple Airlines

Sun 4/2012:48 pmOAK - MDW

2 stops19h 21mMultiple Airlines

Deal found 3/27

$358

Last-minute flights from Chicago to Oakland
Discover last-minute flight deals from Chicago to Oakland. Data last updated March 28, 2025 and is based on user searches.

Tue 4/19:57 pmORD - OAK

2 stops34h 39mMultiple Airlines

Sun 4/67:31 amOAK - ORD

3 stops28h 44mMultiple Airlines

Deal found 3/27

$507

Tue 4/14:20 pmMDW - OAK

Nonstop4h 40mSouthwest

Fri 4/44:50 pmOAK - MDW

1 stop6h 20mSouthwest

Deal found 3/27

$558

Sat 4/58:09 amORD - OAK

1 stop11h 46mSpirit Airlines

Mon 4/141:49 pmOAK - ORD

2 stops22h 14mSpirit Airlines

Deal found 3/26

$273

Sat 4/55:15 pmORD - OAK

1 stop7h 11mDelta

Mon 4/145:10 pmOAK - ORD

1 stop5h 43mDelta

Deal found 3/26

$377

Sat 4/52:04 pmORD - OAK

1 stop7h 33mAlaska Airlines

Mon 4/148:25 pmOAK - ORD

1 stop14h 40mAlaska Airlines

Deal found 3/27

$386

Sat 4/51:12 pmMDW - OAK

2 stops11h 14mDelta

Mon 4/145:10 pmOAK - MDW

2 stops13h 57mDelta

Deal found 3/27

$543

Wed 4/95:53 pmORD - OAK

1 stop7h 50mAlaska Airlines

Wed 4/166:43 amOAK - ORD

1 stop9h 12mAlaska Airlines

Deal found 3/26

$276

Fri 4/189:10 pmMDW - OAK

Nonstop4h 35mSouthwest

Sun 4/205:55 amOAK - MDW

Nonstop4h 10mSouthwest

Deal found 3/27

$237

Fri 4/187:10 pmORD - OAK

1 stop6h 33mDelta

Sun 4/206:00 amOAK - ORD

2 stops9h 04mDelta

Deal found 3/27

$262

Fri 4/1810:59 amMDW - OAK

2 stops26h 54mMultiple Airlines

Sun 4/2012:48 pmOAK - MDW

2 stops19h 21mMultiple Airlines

Deal found 3/27

$358

Sat 4/191:16 pmMDW - OAK

2 stops11h 10mDelta

Sat 4/266:00 amOAK - MDW

2 stops9h 19mDelta

Deal found 3/26

$267

Sat 4/192:04 pmORD - OAK

1 stop7h 33mHawaiian Airlines

Sat 4/269:15 amOAK - ORD

1 stop7h 01mHawaiian Airlines

Deal found 3/26

$321

One-way flights from Chicago to Oakland
Search for one-way flight options from Chicago to Oakland. Find affordable one-way fares based on user searches. Data last updated March 28, 2025.

Tue 4/295:36 amORD - OAK

2 stops31h 01mSpirit Airlines

Deal found 3/26

$76

Sat 5/34:55 pmMDW - OAK

Nonstop4h 35mSouthwest

Deal found 3/27

$99

Tue 4/299:00 amORD - OAK

1 stop8h 48mHawaiian Airlines

Deal found 3/26

$108

Sat 4/191:50 pmORD - OAK

1 stop9h 20mSouthwest

Deal found 3/26

$109

Fri 5/910:59 amMDW - OAK

2 stops28h 08mMultiple Airlines

Deal found 3/27

$122

Sun 4/207:25 amORD - OAK

1 stop6h 48mDelta

Deal found 3/26

$129

Tue 5/61:16 pmMDW - OAK

2 stops12h 27mDelta

Deal found 3/27

$134

Sat 4/265:56 pmORD - OAK

1 stop7h 48mAlaska Airlines

Deal found 3/25

$138

Sun 6/86:30 amORD - OAK

1 stop11h 51mSun Country Air

Deal found 3/27

$153

Thu 5/158:05 pmORD - OAK

3 stops22h 28mMultiple Airlines

Deal found 3/26

$183

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago to Oakland that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Tue 5/6

9:38 pm-10:25 pm

2 stops26h 47m

Oakland

Tue 5/13

9:09 pm-10:55 am

1 stop11h 46m

$172

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Tue 5/6

6:00 am-12:01 pm

1 stop8h 01m

Oakland

Wed 5/7

9:09 pm-10:55 am

1 stop11h 46m

$207

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Fri 4/18

9:10 pm-11:45 pm

Nonstop4h 35m

Oakland

Sun 4/20

5:55 am-12:05 pm

Nonstop4h 10m

$237

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Fri 4/18

7:10 pm-11:43 pm

1 stop6h 33m

Oakland

Sun 4/20

6:00 am-5:04 pm

2 stops9h 04m

$262

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Sat 4/19

1:16 pm-10:26 pm

2 stops11h 10m

Oakland

Sat 4/26

6:00 am-5:19 pm

2 stops9h 19m

$267

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Sat 5/3

9:00 am-3:48 pm

1 stop8h 48m

Oakland

Mon 5/12

7:55 pm-1:07 pm

1 stop15h 12m

$315

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Fri 4/18

10:59 am-11:53 am

2 stops26h 54m

Oakland

Sun 4/20

12:48 pm-10:09 am

2 stops19h 21m

$358

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Wed 6/18

7:00 am-2:00 pm

2 stops9h 00m

Oakland

Tue 6/24

5:15 am-4:45 pm

2 stops9h 30m

$362

ChicagoOakland

ORD - OAK

ORDOAK

Chicago O'Hare Intl

Tue 4/29

5:36 am-10:37 am

2 stops31h 01m

$76

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Sat 5/3

4:55 pm-7:30 pm

Nonstop4h 35m

$99

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/27

Showing 1-10 of 18 results

Compare providers for flights from Chicago to Oakland

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Oakland in March.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy1 star	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*3 stars
eDreams	Price Accuracy3 stars	Trust Score*3 stars
Priceline	Price Accuracy1 star	Trust 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.

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?

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?

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?

Travelers seeking maximum savings on their Chicago to Oakland, California flight should consider departing on Sunday afternoons 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

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

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

Peruse reviews from past customers who have flown with Southwest, Alaska Airlines 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.

Southwest

8.1

Very good

4,274 reviews

Reviews

1 / 20

10.0

Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

Southwest

8.1

Very good

4,274 reviews

Southwest

8.1

Very good

4,274 reviews

Reviews

1 / 20

10.0

Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

Alaska Airlines

8.0

Very good

9,798 reviews

Southwest

8.1

Very good

4,274 reviews

Reviews

1 / 20

10.0

Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

Delta

8.0

Very good

7,897 reviews

Southwest

8.1

Very good

4,274 reviews

Reviews

1 / 20

10.0

Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

Hawaiian Airlines

7.9

Good

2,336 reviews

Southwest

8.1

Very good

4,274 reviews

Reviews

1 / 20

10.0

Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

Sun Country Air

6.9

Okay

348 reviews

Southwest

8.1

Very good

4,274 reviews

Reviews

1 / 20

10.0

Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

Related info for your journey

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 $151 on this airline. Additional options worth looking into are Southwest and Delta, starting at $237 and $262 round-trip. These flights start at 55% 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 $76. 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

Browse thousands of different options on Cheapflights for your next trip

Top 4 airlines flying from Chicago to Oakland

Airline	Cheapest	Average	Flexibility	On-time
Spirit Airlines	Cheapest$129	Average$242	FlexibilityNo cancel fee	On-time65%
Delta	Cheapest$237	Average$628	FlexibilityNo cancel fee	On-timeN/A
Alaska Airlines	Cheapest$238	Average$362	FlexibilityNo cancel fee	On-time75%
Southwest	Cheapest$247	Average$392	FlexibilityNo cancel fee	On-time63%

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$76+ 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 4/29. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Chicago to Oakland with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheapflights Tip: The best prices from Chicago to Oakland are usually found in July or April, booked 28 days in advance, depart on a Thursday or Monday and return on a Sunday

Cheap flight deals from Chicago to Oakland

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Good one-way deal

Find flight deals from Chicago to Oakland

Cheapest flights from Chicago to OaklandExplore 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 March 28, 2025.

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 March 28, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago to Oakland that are best for you.

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 March.

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.

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 March 21, 2025.

What is the cheapest month to book a flight from Chicago to Oakland, California?

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 March 28, 2025.

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 23, 2025.

Rainfall in Oakland by month

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

Temperature in Oakland by month

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

Reviews of airlines servicing Oakland

Peruse reviews from past customers who have flown with Southwest, Alaska Airlines 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.

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?

What are the cheapest airlines flying from Chicago to Oakland, California round-trip?

What are the cheapest airlines to fly from Chicago to Oakland, California one-way?

Can I find deals for flights from Chicago to Oakland that include hotel bookings?

How can I find direct flights from Chicago to Oakland?

Can I find deals for business class flights from Chicago to Oakland?

What is the cheapest month to book a flight from Chicago to Oakland, California?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Oakland

See prices for flight routes from nearby airports that may be better suited for you.

Top 4 airlines flying from Chicago to Oakland

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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 March 28, 2025.