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$120+ 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 4/22. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — BDL
Mar 13 — Mar 201
Fri 3/13
Fri 3/20
1 adult, Economy
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Cheap 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 February 11, 2026.

This CheapOair deal was found by Cheapflights users on 2/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/310:04 am
OAK
-
JFK
1 stop26h 21m
Alaska Airlines
Mon 3/95:00 pm
JFK
-
OAK
1 stop19h 24m
Alaska Airlines
Deal found 2/10$239
This Southwest deal was found by Cheapflights users on 2/8. 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.
Sun 3/15:05 am
OAK
-
LGA
1 stop8h 20m
Southwest
Sat 3/76:25 am
LGA
-
OAK
1 stop10h 30m
Southwest
Deal found 2/8$239
This Southwest deal was found by Cheapflights users on 2/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1011:55 pm
OAK
-
LGA
1 stop12h 40m
Southwest
Wed 4/152:15 pm
LGA
-
OAK
1 stop10h 50m
Southwest
Deal found 2/9$244
This Kiwi.com deal was found by Cheapflights users on 2/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:15 am
OAK
-
JFK
1 stop9h 55m
Hawaiian Airlines
Wed 3/44:25 pm
JFK
-
OAK
1 stop9h 24m
Hawaiian Airlines
Deal found 2/8$246
This Southwest deal was found by Cheapflights users on 2/8. 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.
Tue 3/1010:25 am
OAK
-
LGA
2 stops9h 05m
Southwest
Tue 3/1711:00 am
LGA
-
OAK
2 stops11h 15m
Southwest
Deal found 2/8$249
This CheapOair deal was found by Cheapflights users on 2/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2810:04 am
OAK
-
JFK
1 stop26h 41m
Alaska Airlines
Thu 3/54:25 pm
JFK
-
OAK
1 stop10h 29m
Alaska Airlines
Deal found 2/11$253
This Southwest deal was found by Cheapflights users on 2/8. 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.
Sat 2/286:40 am
OAK
-
LGA
1 stop7h 20m
Southwest
Wed 3/42:00 pm
LGA
-
OAK
1 stop11h 15m
Southwest
Deal found 2/8$253
This Southwest deal was found by Cheapflights users on 2/10. 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.
Tue 3/249:00 am
OAK
-
LGA
2 stops10h 30m
Southwest
Tue 3/316:00 am
LGA
-
OAK
2 stops15h 35m
Southwest
Deal found 2/10$255
This Southwest deal was found by Cheapflights users on 2/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/286:40 am
OAK
-
LGA
1 stop7h 20m
Southwest
Tue 3/311:25 am
LGA
-
OAK
2 stops12h 10m
Southwest
Deal found 2/9$258
This CheapOair deal was found by Cheapflights users on 2/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/45:31 pm
OAK
-
JFK
1 stop10h 34m
Alaska Airlines
Sat 3/75:00 pm
JFK
-
OAK
1 stop18h 24m
Alaska Airlines
Deal found 2/11$259
This CheapOair deal was found by Cheapflights users on 2/8. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/2510:04 am
OAK
-
JFK
1 stop26h 41m
Alaska Airlines
Sat 2/285:00 pm
JFK
-
OAK
1 stop19h 24m
Alaska Airlines
Deal found 2/8$267
This CheapOair deal was found by Cheapflights users on 2/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:15 am
OAK
-
JFK
1 stop9h 55m
Alaska Airlines
Wed 3/44:25 pm
JFK
-
OAK
1 stop9h 24m
Alaska Airlines
Deal found 2/10$268

Find flight deals from Oakland to Connecticut

Keep the following information in mind while searching for Oakland to Connecticut flight deals. Data was last updated February 11, 2026.

Round-trip from

$239
(CheapOair)

One-way from

$120
(Southwest)

Popular in

April

Cheapest in

January

Average price

$440
From Oakland to Connecticut
Search Deals
One-way flight from Oakland to Connecticut
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($38 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 February 2026
Search Deals

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 February 11, 2026.
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

Tue 3/24

9:25 am-9:00 pm

1 stop8h 35m

New York LaGuardia

Tue 3/31

2:10 pm-10:00 pm

1 stop10h 50m

$239

OaklandNew York

OAK - LGA

OAKLGA

Oakland

Tue 4/14

7:40 am-7:15 pm

1 stop8h 35m

New York LaGuardia

Tue 4/21

3:55 pm-11:25 pm

1 stop10h 30m

$239

OaklandNew York

OAK - LGA

OAKLGA

Oakland

Tue 5/5

9:25 am-8:30 pm

1 stop8h 05m

New York LaGuardia

Tue 5/19

3:55 pm-11:25 pm

1 stop10h 30m

$239

OaklandNew York

OAK - LGA

OAKLGA

Oakland

Sun 3/1

5:05 am-4:25 pm

1 stop8h 20m

New York LaGuardia

Sat 3/7

6:25 am-1:55 pm

1 stop10h 30m

$239

OaklandNew York

OAK - LGA

OAKLGA

Oakland

Thu 4/2

11:20 am-11:25 pm

1 stop9h 05m

New York LaGuardia

Tue 4/7

7:15 am-4:00 pm

2 stops11h 45m

$244

OaklandNew York

OAK - LGA

OAKLGA

Oakland

Thu 4/23

8:55 pm-11:50 am

1 stop11h 55m

New York LaGuardia

Mon 4/27

5:50 pm-12:25 am

1 stop9h 35m

$244

OaklandNew York

OAK - LGA

OAKLGA

Oakland

Thu 5/7

8:55 pm-11:50 am

1 stop11h 55m

New York LaGuardia

Tue 5/12

4:30 pm-10:05 pm

1 stop8h 35m

$244

OaklandNew York

OAK - JFK

OAKJFK

Oakland

Tue 4/14

6:40 pm-7:12 am

1 stop9h 32m

New York John F Kennedy Intl

Tue 4/21

9:30 am-10:17 am

1 stop27h 47m

$291

OaklandNewark

OAK - EWR

OAKEWR

Oakland

Tue 3/10

12:35 pm-11:59 pm

1 stop8h 24m

Newark

Tue 3/17

6:30 pm-11:46 pm

1 stop8h 16m

$297

OaklandNew York

OAK - JFK

OAKJFK

Oakland

Tue 2/24

6:15 am-7:10 pm

1 stop9h 55m

New York John F Kennedy Intl

Wed 2/25

4:25 pm-10:49 pm

1 stop9h 24m

$297

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/8

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 April is currently the most expensive (average of $302). 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.

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 February 11, 2026.
Read through reviews of airlines operating flights from Oakland to Connecticut, such as Southwest. 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
4,280 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Southwest
8.0
Very good
4,280 reviews
Southwest
8.0
Very good
4,280 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.

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 8h 24m. Fly via Southwest, Alaska Airlines, or Delta to get the fastest option. The distance from Oakland, California to Connecticut is about 2547 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    Most travelers choose Oakland - New York John F Kennedy Intl, Oakland - Newark 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 April is currently the most expensive (average of $302). 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 airline flying from Oakland to Connecticut

Discover the top airline 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 February 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$381Average$525FlexibilityNo cancel feeOn-time63%

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