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$129+ Cheap flights from Oakland, CA to Boston (OAK - BOS)

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 12/10. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — BOS
Oct 29 — Nov 51
Wed 10/29
Wed 11/5
1 adult, Economy
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Cheapflights Tip: The best prices from Oakland to Boston Logan Intl are usually found in September or November, booked 74 days in advance, depart on a Saturday or Tuesday and return on a Thursday

Cheap flight deals from Oakland to Boston

Discover tips and strategies to find the most affordable flight options for your journey from Oakland (OAK) to Boston (BOS). 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 September 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$269
(Southwest)

One-way from

$129
(Southwest)

Popular in

April

Cheapest in

September

Average price

$327
Provider with most accurate pricing for Oakland-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Oakland-Boston Logan Intl flights.
Search Deals
From Oakland to Boston Logan Intl
Search Deals
One-way flight from Oakland to Boston Logan Intl
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($51 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
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Find flight deals from Oakland to Boston

Cheapest flights from Oakland to Boston
Explore the most affordable flight options available from Oakland to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 29, 2025.

This Southwest deal was found by Cheapflights users on 9/27. 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.
Wed 12/1012:35 pmOAK - BOS
1 stop7h 10mSouthwest
Tue 12/166:45 amBOS - OAK
1 stop10h 55mSouthwest
Deal found 9/27$269
This Alaska Airlines deal was found by Cheapflights users on 9/27. 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 10/229:25 amOAK - BOS
1 stop17h 35mAlaska Airlines
Wed 10/297:00 amBOS - OAK
1 stop9h 55mAlaska Airlines
Deal found 9/27$288
This Alaska Airlines deal was found by Cheapflights users on 9/28. 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.
Tue 10/286:30 amOAK - BOS
1 stop14h 50mAlaska Airlines
Tue 11/47:00 amBOS - OAK
1 stop30h 25mAlaska Airlines
Deal found 9/28$290
This Southwest deal was found by Cheapflights users on 9/28. 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.
Tue 10/2812:45 pmOAK - BOS
1 stop7h 40mSouthwest
Tue 11/46:45 amBOS - OAK
2 stops10h 10mSouthwest
Deal found 9/28$293
This Alaska Airlines deal was found by Cheapflights users on 9/27. 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 11/19:30 amOAK - BOS
2 stops11h 50mAlaska Airlines
Wed 11/57:00 amBOS - OAK
1 stop9h 55mAlaska Airlines
Deal found 9/27$295
This Delta deal was found by Cheapflights users on 9/27. 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 12/84:50 pmOAK - BOS
1 stop10h 28mDelta
Mon 12/156:46 pmBOS - OAK
1 stop8h 22mDelta
Deal found 9/27$299
This Southwest deal was found by Cheapflights users on 9/28. 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.
Thu 11/65:45 amOAK - BOS
2 stops9h 55mSouthwest
Mon 11/106:20 pmBOS - OAK
1 stop8h 50mSouthwest
Deal found 9/28$314
This Southwest deal was found by Cheapflights users on 9/27. 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.
Tue 10/145:20 amOAK - BOS
1 stop8h 35mSouthwest
Tue 10/212:05 pmBOS - OAK
1 stop9h 45mSouthwest
Deal found 9/27$317
This Southwest deal was found by Cheapflights users on 9/28. 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 11/75:45 amOAK - BOS
2 stops9h 55mSouthwest
Tue 11/116:45 amBOS - OAK
2 stops10h 10mSouthwest
Deal found 9/28$319

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oakland to Boston 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 September 29, 2025.
Use the filters below to find and compare flights from Oakland to Boston that are best for you.

Fly from

Oakland

Fly to

Boston

Route

Depart

Return

Price

OaklandBoston

OAK - BOS

OAKBOS

Oakland

Wed 10/22

9:25 am-6:00 am

1 stop17h 35m

Boston Logan Intl

Wed 10/29

7:00 am-1:55 pm

1 stop9h 55m

$288

OaklandBoston

OAK - BOS

OAKBOS

Oakland

Tue 3/3

6:35 pm-7:16 am

1 stop9h 41m

Boston Logan Intl

Wed 3/4

10:00 am-5:43 pm

1 stop10h 43m

$313

OaklandBoston

OAK - BOS

OAKBOS

Oakland

Thu 11/6

5:45 am-6:40 pm

2 stops9h 55m

Boston Logan Intl

Mon 11/10

6:20 pm-12:10 am

1 stop8h 50m

$314

OaklandBoston

OAK - BOS

OAKBOS

Oakland

Tue 10/14

5:20 am-4:55 pm

1 stop8h 35m

Boston Logan Intl

Tue 10/21

2:05 pm-8:50 pm

1 stop9h 45m

$317

OaklandBoston

OAK - BOS

OAKBOS

Oakland

Thu 11/6

6:50 am-7:15 pm

1 stop9h 25m

Boston Logan Intl

Sun 11/9

6:20 pm-12:10 am

1 stop8h 50m

$352

OaklandBoston

OAK - BOS

OAKBOS

Oakland

Mon 12/22

7:15 pm-8:10 am

2 stops9h 55m

Boston Logan Intl

Mon 1/5

12:05 pm-8:50 pm

2 stops11h 45m

$358

OaklandBoston

OAK - BOS

OAKBOS

Oakland

Sun 11/2

5:30 am-6:29 am

1 stop21h 59m

Boston Logan Intl

Fri 11/7

7:00 am-11:59 pm

1 stop19h 59m

$362

OaklandBoston

OAK - BOS

OAKBOS

Oakland

Mon 12/8

4:50 pm-6:18 am

1 stop10h 28m

Boston Logan Intl

Tue 12/16

2:35 pm-12:08 am

2 stops12h 33m

$364

OaklandBoston

OAK - BOS

OAKBOS

Oakland

Wed 12/10

12:35 pm-10:45 pm

1 stop7h 10m

$129

OaklandBoston

OAK - BOS

OAKBOS

Oakland

Wed 12/17

12:35 pm-10:45 pm

1 stop7h 10m

$129

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/27

Showing 1-10 of 19 results
1
2

Compare providers for flights from Oakland to Boston

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 Oakland to Boston in September.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 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 Oakland, California-Boston flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Oakland, California-Boston flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Oakland, California-Boston flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Oakland, California-Boston 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 Oakland, California-Boston 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 Oakland to Boston

Have a flexible travel schedule? Discover the best time to fly to Boston from Oakland 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 Oakland to Boston

How far ahead should I book a flight from Oakland, California to Boston?

Use this chart to determine the optimal time to book a round-trip flight from Oakland to Boston. Price data was last updated on September 26, 2025.

Booking 74 days in advance of your planned departure date is, on average, the best time to get cheap flights from Oakland, California to Boston. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Currently, January is the cheapest month in which you can book a flight from Oakland, California to Boston (average of $218). Flying from Oakland, California to Boston in July is currently the most expensive (average of $311). 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 OAK to BOS?

Find hourly flight availability from Oakland to Boston. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 29, 2025.

When flying from Oakland, California to Boston, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 24% versus a flight in the afternoon.

What is the cheapest day to fly from Oakland, California to Boston?

Use this chart to determine the cheapest time to fly round-trip from Oakland to Boston. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Oakland, California to Boston flight should consider departing on Friday evenings when fares are most often at their lowest. Thursday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Boston

Get insights into the airlines that provide service to Boston. 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 Boston. Reviews last updated September 29, 2025.
Read through reviews of airlines operating flights from Oakland to Boston, such as Alaska Airlines, Southwest, and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Southwest
8.0
Very good
4,246 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Delta
8.0
Very good
7,964 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
United Airlines
7.4
Good
8,924 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
JetBlue
7.2
Good
2,912 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.

Related info for your journey

Find useful and relevant information for your journey from Oakland to Boston. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Oakland, California to Boston?

    A quick flight from Oakland, California to Boston can take about 9h 55m. Alaska Airlines provides one of the quickest options available for as low as $314. The distance between Oakland, California and Boston is about 2685 mi. This flight may include one or multiple stops.

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

    Currently priced at $148, JetBlue will fly you from Oakland, California to Boston and back. In addition to JetBlue, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Delta and United Airlines - these airlines can fly you to your destination from $227 and $228, respectively. JetBlue is priced at 63% lower than the current average price of a flight leaving 3 months from now.

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

    Yes. In addition to deals on Oakland to Boston flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Oakland to Boston?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Oakland to Boston.

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

    Yes. Cheapflights offers flight deals from Oakland to Boston 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 Oakland, California to Boston?

    Currently, January is the cheapest month in which you can book a flight from Oakland, California to Boston (average of $218). Flying from Oakland, California to Boston in July is currently the most expensive (average of $311). 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

Traveling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
Cambridge
Medford
Hampton Beach
Watertown
Seabrook
Seekonk
Lincoln
Lowell
Smithfield
Cranston
Chestnut Hill
Warwick
Peabody
Quincy
York Beach
Swansea
Old Orchard Beach
Brockton
Waltham
Chelsea

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Top 5 airlines flying from Oakland to Boston

Discover the top 5 airlines that operate flights from Oakland to Boston. 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 September 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$148Average$288FlexibilityNo cancel feeOn-time62%
DeltaCheapest$227Average$416FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$228Average$329FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$289Average$470FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$324Average$475FlexibilityNo cancel feeOn-time63%

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