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$87+ Cheap flights from Oakland, CA (OAK) to Connecticut

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 2/3. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — BDL
Nov 19 — Nov 261
Wed 11/19
Wed 11/26
1 adult, Economy
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Find flight deals from Oakland to Connecticut

Cheapest flights from Oakland to Connecticut
Explore the most affordable flight options available from Oakland to Connecticut. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 20, 2025.

This KAYAK deal was found by Cheapflights users on 10/18. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/18:03 pmOAK - JFK
1 stop9h 17mAlaska Airlines
Wed 11/197:00 amJFK - OAK
1 stop9h 55mAlaska Airlines
Deal found 10/18$262
This Southwest deal was found by Cheapflights users on 10/20. 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.
Wed 11/125:45 amOAK - LGA
1 stop9h 10mSouthwest
Fri 11/142:35 pmLGA - OAK
2 stops11h 20mSouthwest
Deal found 10/20$262
This Southwest deal was found by Cheapflights users on 10/18. 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 11/148:00 amOAK - LGA
2 stops12h 25mSouthwest
Sat 11/221:45 pmLGA - OAK
2 stops13h 40mSouthwest
Deal found 10/18$263
This Southwest deal was found by Cheapflights users on 10/20. 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.
Wed 12/3112:35 pmOAK - LGA
1 stop7h 20mSouthwest
Thu 1/811:25 amLGA - OAK
2 stops12h 10mSouthwest
Deal found 10/20$265
This KAYAK deal was found by Cheapflights users on 10/20. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1011:21 amOAK - JFK
1 stop8h 38mAlaska Airlines
Wed 1/77:00 amJFK - OAK
1 stop12h 23mAlaska Airlines
Deal found 10/20$267
This Southwest deal was found by Cheapflights users on 10/20. 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.
Wed 12/37:50 amOAK - LGA
1 stop10h 35mSouthwest
Tue 12/911:15 amLGA - OAK
2 stops13h 15mSouthwest
Deal found 10/20$268
This Cheapflightsfares deal was found by Cheapflights users on 10/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/128:03 pmOAK - JFK
1 stop8h 50mAlaska Airlines
Wed 12/107:00 amJFK - OAK
1 stop9h 32mAlaska Airlines
Deal found 10/19$279
This Southwest deal was found by Cheapflights users on 10/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/11:10 pmOAK - LGA
1 stop7h 05mSouthwest
Sat 11/153:15 pmLGA - OAK
1 stop8h 15mSouthwest
Deal found 10/19$282
This KAYAK deal was found by Cheapflights users on 10/18. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/18:03 pmOAK - JFK
1 stop9h 17mAlaska Airlines
Wed 11/57:00 amJFK - OAK
1 stop9h 55mAlaska Airlines
Deal found 10/18$286
This Alaska Airlines deal was found by Cheapflights users on 10/18. 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 12/1011:21 amOAK - JFK
1 stop8h 38mAlaska Airlines
Sat 12/136:55 pmJFK - OAK
1 stop18h 46mAlaska Airlines
Deal found 10/18$287
This Southwest deal was found by Cheapflights users on 10/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/135:25 amOAK - LGA
1 stop8h 00mSouthwest
Mon 11/176:30 amLGA - OAK
1 stop10h 35mSouthwest
Deal found 10/19$287
This Southwest deal was found by Cheapflights users on 10/18. 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 12/512:35 pmOAK - LGA
1 stop7h 20mSouthwest
Tue 12/911:15 amLGA - OAK
2 stops13h 15mSouthwest
Deal found 10/18$292

Cheap flight deals from Oakland to Connecticut

Keep the following information in mind while searching for Oakland to Connecticut flight deals. Data was last updated October 20, 2025.

Round-trip from

$262
(Alaska Airlines)

One-way from

$87
(Southwest)

Popular in

November

Cheapest in

August

Average price

$453
From Oakland to Connecticut
Search Deals
One-way flight from Oakland to Connecticut
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($59 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Oakland to Connecticut 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 October 20, 2025.
Use the filters below to find and compare flights from Oakland to Connecticut that are best for you.

Fly from

Oakland

Fly to

Connecticut

Route

Depart

Return

Price

OaklandNew York

OAK - JFK

OAKJFK

Oakland

Thu 1/15

8:10 am-7:28 pm

1 stop8h 18m

New York John F Kennedy Intl

Tue 1/20

7:00 am-4:23 pm

1 stop12h 23m

$262

OaklandNew York

OAK - LGA

OAKLGA

Oakland

Wed 12/31

12:35 pm-10:55 pm

1 stop7h 20m

New York LaGuardia

Thu 1/8

11:25 am-8:35 pm

2 stops12h 10m

$265

OaklandNew York

OAK - LGA

OAKLGA

Oakland

Wed 12/3

7:50 am-9:25 pm

1 stop10h 35m

New York LaGuardia

Tue 12/9

11:15 am-9:30 pm

2 stops13h 15m

$268

OaklandNew York

OAK - LGA

OAKLGA

Oakland

Thu 1/15

8:30 am-8:10 pm

1 stop8h 40m

New York LaGuardia

Tue 1/20

2:30 pm-10:15 pm

2 stops10h 45m

$271

OaklandNew York

OAK - LGA

OAKLGA

Oakland

Sat 11/1

1:10 pm-11:15 pm

1 stop7h 05m

New York LaGuardia

Sat 11/15

3:15 pm-8:30 pm

1 stop8h 15m

$282

OaklandNew York

OAK - LGA

OAKLGA

Oakland

Thu 11/13

5:25 am-4:25 pm

1 stop8h 00m

New York LaGuardia

Mon 11/17

6:30 am-2:05 pm

1 stop10h 35m

$287

OaklandNew York

OAK - LGA

OAKLGA

Oakland

Wed 12/10

12:35 pm-10:55 pm

1 stop7h 20m

New York LaGuardia

Sat 12/13

6:00 am-2:25 pm

1 stop11h 25m

$292

OaklandNew York

OAK - LGA

OAKLGA

Oakland

Fri 12/5

12:35 pm-10:55 pm

1 stop7h 20m

New York LaGuardia

Tue 12/9

11:15 am-9:30 pm

2 stops13h 15m

$292

OaklandNew York

OAK - JFK

OAKJFK

Oakland

Tue 11/11

8:03 pm-7:53 am

1 stop8h 50m

New York John F Kennedy Intl

Sat 11/15

6:49 pm-10:25 am

1 stop18h 36m

$306

OaklandNew York

OAK - JFK

OAKJFK

Oakland

Sat 11/15

2:49 pm-7:53 am

1 stop14h 04m

New York John F Kennedy Intl

Tue 11/18

7:00 am-1:55 pm

1 stop9h 55m

$306

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/19

Showing 1-10 of 60 results
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Best time to book a flight from Oakland to Connecticut

Have a flexible travel schedule? Discover the best time to fly to Connecticut 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 Connecticut

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

Currently, August is the cheapest month in which you can book a flight from Oakland, California to Connecticut (average of $190). Flying from Oakland, California to Connecticut in February is currently the most expensive (average of $375). 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 CT?

Find hourly flight availability from Oakland to Connecticut. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 20, 2025.

It’s typically best to fly out from Oakland, California to Connecticut at noon. Doing so could potentially save you 61% on the flight price compared to flying in the afternoon, which is usually more expensive.

How much does it cost to fly round-trip from Oakland, California to Connecticut?

Reviews of airlines servicing Connecticut

Get insights into the airlines that provide service to Connecticut. 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 Connecticut. Reviews last updated October 20, 2025.
Read through reviews of airlines operating flights from Oakland to Connecticut, such as Southwest and Delta. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,239 reviews

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,239 reviews
Southwest
8.0
Very good
4,239 reviews

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Delta
7.9
Good
7,978 reviews
Southwest
8.0
Very good
4,239 reviews

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Related info for your journey

Find useful and relevant information for your journey from Oakland to Connecticut. 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 from for flights from Oakland to Connecticut?

    For a flight from Oakland to Connecticut, you will be flying from Oakland. Oakland (OAK) is just 7.0 mi from the center of the city.

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

    There are many flights that can get you from Oakland, California to Connecticut in 7h 20m. Fly via Alaska Airlines, Southwest, or Delta to get the fastest option. The distance from Oakland, California to Connecticut is about 2561 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $87. Alaska Airlines flights start at $129 while deals on Delta start at $154 one-way.

  • What are the most popular routes from Oakland, California to Connecticut?

    Most travelers choose Oakland - Newark, Oakland - New York John F Kennedy Intl or Oakland - New York LaGuardia when deciding on the best route from Oakland, California to Connecticut.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Oakland to Connecticut 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 Connecticut?

    Currently, August is the cheapest month in which you can book a flight from Oakland, California to Connecticut (average of $190). Flying from Oakland, California to Connecticut in February is currently the most expensive (average of $375). 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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Alternative routes for Oakland to Connecticut

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Oakland to Connecticut

Discover the top 2 airlines that operate flights from Oakland to Connecticut. 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 October 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$296Average$474FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$381Average$542FlexibilityNo cancel feeOn-time63%

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