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$99+ 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 1/18. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — BDL
Dec 10 — Dec 171
Wed 12/10
Wed 12/17
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 November 10, 2025.

This Southwest deal was found by Cheapflights users on 11/10. 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 - LGA
1 stop7h 20mSouthwest
Mon 12/156:30 amLGA - OAK
1 stop10h 35mSouthwest
Deal found 11/10$264
This Southwest deal was found by Cheapflights users on 11/8. 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 12/96:30 amLGA - OAK
1 stop10h 35mSouthwest
Deal found 11/8$266
This Alaska Airlines deal was found by Cheapflights users on 11/8. 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 12/66:40 amOAK - JFK
1 stop9h 49mAlaska Airlines
Tue 12/97:00 amJFK - OAK
1 stop9h 32mAlaska Airlines
Deal found 11/8$282
This Southwest deal was found by Cheapflights users on 11/8. 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 - LGA
1 stop7h 20mSouthwest
Tue 12/1611:40 amLGA - OAK
1 stop10h 00mSouthwest
Deal found 11/8$294
This Southwest deal was found by Cheapflights users on 11/8. 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 12/109:50 amOAK - LGA
2 stops9h 05mSouthwest
Sat 12/136:10 amLGA - OAK
1 stop13h 55mSouthwest
Deal found 11/8$305
This Delta deal was found by Cheapflights users on 11/8. 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.
Sat 12/65:55 amOAK - JFK
2 stops11h 44mDelta
Thu 12/112:53 pmJFK - OAK
2 stops12h 15mDelta
Deal found 11/8$307
This Delta deal was found by Cheapflights users on 11/10. 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.
Wed 12/35:55 amOAK - LGA
2 stops10h 10mDelta
Fri 12/54:56 pmLGA - OAK
2 stops10h 12mDelta
Deal found 11/10$307
This Alaska Airlines deal was found by Cheapflights users on 11/9. 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 12/166:40 amOAK - EWR
1 stop28h 49mAlaska Airlines
Sat 1/176:08 pmEWR - OAK
1 stop19h 20mAlaska Airlines
Deal found 11/9$307
This Cheapflightsfares deal was found by Cheapflights users on 11/8. 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.
Fri 12/56:40 amOAK - EWR
1 stop8h 46mAlaska Airlines
Wed 12/107:14 amEWR - OAK
1 stop9h 18mAlaska Airlines
Deal found 11/8$309
This Alaska Airlines deal was found by Cheapflights users on 11/9. 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 12/162:31 pmOAK - JFK
2 stops12h 55mAlaska Airlines
Sun 1/187:00 amJFK - OAK
1 stop12h 23mAlaska Airlines
Deal found 11/9$311
This Southwest deal was found by Cheapflights users on 11/7. 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 11/175:45 amOAK - LGA
1 stop6h 55mSouthwest
Mon 11/2411:00 amLGA - OAK
2 stops14h 55mSouthwest
Deal found 11/7$313
This Delta deal was found by Cheapflights users on 11/8. 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.
Wed 12/105:55 amOAK - LGA
2 stops10h 25mDelta
Tue 12/161:56 pmLGA - OAK
2 stops13h 12mDelta
Deal found 11/8$316

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 November 10, 2025.

Round-trip from

$263
(Southwest)

One-way from

$99
(Southwest)

Popular in

November

Cheapest in

August

Average price

$595
From Oakland to Connecticut
Search Deals
One-way flight from Oakland to Connecticut
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($49 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 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 November 10, 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 - LGA

OAKLGA

Oakland

Wed 3/4

9:20 am-10:40 pm

2 stops10h 20m

New York LaGuardia

Tue 3/10

11:00 am-6:55 pm

1 stop10h 55m

$272

OaklandNew York

OAK - LGA

OAKLGA

Oakland

Thu 1/29

7:50 am-9:00 pm

2 stops10h 10m

New York LaGuardia

Wed 2/4

10:55 am-7:45 pm

2 stops11h 50m

$277

OaklandNew York

OAK - JFK

OAKJFK

Oakland

Sat 12/6

6:40 am-7:29 pm

1 stop9h 49m

New York John F Kennedy Intl

Tue 12/9

7:00 am-1:32 pm

1 stop9h 32m

$282

OaklandNew York

OAK - JFK

OAKJFK

Oakland

Wed 2/4

11:08 am-10:52 pm

1 stop8h 44m

New York John F Kennedy Intl

Sun 2/8

7:00 am-4:23 pm

1 stop12h 23m

$282

OaklandNew York

OAK - LGA

OAKLGA

Oakland

Tue 12/9

5:45 am-5:55 pm

1 stop9h 10m

New York LaGuardia

Sat 12/13

6:10 am-5:05 pm

1 stop13h 55m

$299

OaklandNew York

OAK - LGA

OAKLGA

Oakland

Wed 12/3

5:55 am-7:05 pm

2 stops10h 10m

New York LaGuardia

Thu 12/4

1:56 pm-12:08 am

2 stops13h 12m

$307

OaklandNew York

OAK - LGA

OAKLGA

Oakland

Wed 12/3

5:55 am-7:05 pm

2 stops10h 10m

New York LaGuardia

Fri 12/5

4:56 pm-12:08 am

2 stops10h 12m

$307

OaklandNew York

OAK - LGA

OAKLGA

Oakland

Tue 12/9

4:50 pm-8:45 am

2 stops12h 55m

New York LaGuardia

Tue 12/16

1:56 pm-12:08 am

2 stops13h 12m

$307

OaklandNew York

OAK - LGA

OAKLGA

Oakland

Thu 11/27

5:55 am-7:42 pm

2 stops10h 47m

New York LaGuardia

Thu 12/4

1:56 pm-12:08 am

2 stops13h 12m

$307

OaklandNew York

OAK - LGA

OAKLGA

Oakland

Sat 12/6

5:55 am-7:29 pm

2 stops10h 34m

New York LaGuardia

Wed 12/10

1:56 pm-12:08 am

2 stops13h 12m

$307

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/10

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 $187). 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 November 10, 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.

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 November 10, 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
4,235 reviews

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

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
4,235 reviews
Southwest
8.0
Very good
4,235 reviews

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

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
8,006 reviews
Southwest
8.0
Very good
4,235 reviews

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

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 9h 49m. Fly via Southwest, Alaska Airlines, or Delta to get the fastest option. The distance from Oakland, California to Connecticut is about 2568 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 $106. Alaska Airlines flights start at $129 while deals on Delta start at $185 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 $187). 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

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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 November 10, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$296Average$474FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$381Average$533FlexibilityNo cancel feeOn-time63%

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