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$98+ Cheap flights from Connecticut 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 10/28. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — OAK
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap flight deals from Connecticut to Oakland

Keep the following information in mind while searching for Connecticut to Oakland flight deals. Data was last updated September 17, 2025.

Round-trip from

$200
(Southwest)

One-way from

$98
(Southwest)

Popular in

December

Cheapest in

August

Average price

$396
From Connecticut to Oakland
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One-way flight from Connecticut to Oakland
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Highest demand for flights based on searches. 10% potential increase in price ($50 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Connecticut to Oakland

Cheapest flights from Connecticut to Oakland
Explore the most affordable flight options available from Connecticut to Oakland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

This Southwest deal was found by Cheapflights users on 9/16. 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 10/256:10 amLGA - OAK
1 stop10h 50mSouthwest
Sat 11/17:45 amOAK - LGA
1 stop11h 55mSouthwest
Deal found 9/16$200
This Southwest deal was found by Cheapflights users on 9/16. 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 11/72:45 pmLGA - OAK
1 stop9h 30mSouthwest
Tue 11/115:45 amOAK - LGA
1 stop6h 50mSouthwest
Deal found 9/16$226
This Southwest deal was found by Cheapflights users on 9/17. 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 11/142:00 pmLGA - OAK
2 stops12h 15mSouthwest
Mon 11/175:45 amOAK - LGA
1 stop9h 10mSouthwest
Deal found 9/17$231
This Priceline deal was found by Cheapflights users on 9/16. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/110:55 amEWR - OAK
2 stops15h 37mSpirit Airlines
Thu 10/26:30 amOAK - EWR
2 stops13h 36mSpirit Airlines
Deal found 9/16$245
This CheapOair deal was found by Cheapflights users on 9/16. 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 10/110:55 amEWR - OAK
2 stops15h 37mSpirit Airlines
Fri 10/36:30 amOAK - EWR
2 stops13h 36mSpirit Airlines
Deal found 9/16$254
This Southwest deal was found by Cheapflights users on 9/16. 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 10/212:15 pmLGA - OAK
1 stop9h 45mSouthwest
Sat 10/251:10 pmOAK - LGA
1 stop7h 05mSouthwest
Deal found 9/16$257
This Southwest deal was found by Cheapflights users on 9/15. 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 10/2111:40 amLGA - OAK
1 stop10h 10mSouthwest
Sun 10/268:40 pmOAK - LGA
1 stop12h 35mSouthwest
Deal found 9/15$262
This CheapOair deal was found by Cheapflights users on 9/16. 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 9/3010:55 amEWR - OAK
2 stops15h 37mSpirit Airlines
Thu 10/26:30 amOAK - EWR
2 stops13h 36mSpirit Airlines
Deal found 9/16$264
This Southwest deal was found by Cheapflights users on 9/14. 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 11/143:35 pmLGA - OAK
2 stops10h 40mSouthwest
Tue 11/189:00 amOAK - LGA
2 stops9h 00mSouthwest
Deal found 9/14$267
This Southwest deal was found by Cheapflights users on 9/15. 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 10/811:40 amLGA - OAK
1 stop10h 10mSouthwest
Wed 10/156:15 amOAK - LGA
2 stops13h 10mSouthwest
Deal found 9/15$268
This CheapOair deal was found by Cheapflights users on 9/14. 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.
Mon 9/299:59 amLGA - OAK
2 stops16h 33mSpirit Airlines
Tue 9/306:30 amOAK - LGA
2 stops13h 08mSpirit Airlines
Deal found 9/14$276
This Booking.com deal was found by Cheapflights users on 9/15. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2910:55 amEWR - OAK
2 stops15h 37mSpirit Airlines
Tue 9/306:30 amOAK - EWR
2 stops13h 36mSpirit Airlines
Deal found 9/15$277

Cheapflights Fare Finder

 
Customize your flight search to find flights from Connecticut to Oakland 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 17, 2025.
Use the filters below to find and compare flights from Connecticut to Oakland that are best for you.

Fly from

Connecticut

Fly to

Oakland

Route

Depart

Return

Price

New YorkOakland

LGA - OAK

LGAOAK

New York LaGuardia

Sat 10/25

6:10 am-2:00 pm

1 stop10h 50m

Oakland

Sat 11/1

7:45 am-10:40 pm

1 stop11h 55m

$200

New YorkOakland

LGA - OAK

LGAOAK

New York LaGuardia

Fri 11/14

2:35 pm-10:00 pm

1 stop10h 25m

Oakland

Mon 11/17

5:45 am-5:55 pm

1 stop9h 10m

$226

New YorkOakland

LGA - OAK

LGAOAK

New York LaGuardia

Fri 11/7

2:45 pm-9:15 pm

1 stop9h 30m

Oakland

Tue 11/11

5:45 am-3:35 pm

1 stop6h 50m

$226

New YorkOakland

LGA - OAK

LGAOAK

New York LaGuardia

Tue 10/21

2:15 pm-9:00 pm

1 stop9h 45m

Oakland

Sat 10/25

1:10 pm-11:15 pm

1 stop7h 05m

$257

New YorkOakland

LGA - OAK

LGAOAK

New York LaGuardia

Fri 11/14

2:00 pm-10:45 pm

1 stop11h 45m

Oakland

Tue 11/18

5:45 am-5:55 pm

1 stop9h 10m

$257

New YorkOakland

LGA - OAK

LGAOAK

New York LaGuardia

Tue 10/21

7:20 am-2:30 pm

2 stops10h 10m

Oakland

Sun 10/26

8:40 pm-12:15 pm

1 stop12h 35m

$268

New YorkOakland

JFK - OAK

JFKOAK

New York John F Kennedy Intl

Wed 10/29

7:00 am-1:55 pm

1 stop9h 55m

Oakland

Tue 11/4

6:30 am-7:29 pm

1 stop9h 59m

$287

New YorkOakland

JFK - OAK

JFKOAK

New York John F Kennedy Intl

Tue 10/28

7:00 am-1:55 pm

1 stop9h 55m

Oakland

Tue 11/4

6:30 am-7:29 pm

1 stop9h 59m

$287

New YorkOakland

JFK - OAK

JFKOAK

New York John F Kennedy Intl

Tue 10/28

4:51 pm-11:59 pm

1 stop10h 08m

Oakland

Sun 11/2

5:30 am-6:29 pm

1 stop9h 59m

$287

New YorkOakland

LGA - OAK

LGAOAK

New York LaGuardia

Wed 10/8

2:15 pm-9:00 pm

1 stop9h 45m

Oakland

Sun 10/12

6:10 am-10:55 pm

1 stop13h 45m

$292

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

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

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

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

Currently, April is the cheapest month in which you can book a flight from Connecticut to Oakland, California (average of $183). Flying from Connecticut 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 CT to OAK?

Find hourly flight availability from Connecticut 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 September 17, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Connecticut to Oakland, California as you normally would.

Related info for your journey

Find useful and relevant information for your journey from Connecticut 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 Connecticut?

    Oakland (OAK) is the airport you will fly into if you book a flight from Connecticut to Oakland. It is only a 7.0 mi journey from Oakland (OAK) to Oakland’s city center.

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

    A quick flight from Connecticut to Oakland, California can take about 9h 55m. Southwest provides one of the quickest options available for as low as $287. The distance between Connecticut and Oakland, California is about 2568 mi. This flight may include one or multiple stops.

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

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $125. Users have also found prices from $129 and $154 on Southwest and Delta, respectively.

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

    When deciding which route to take from Connecticut to Oakland, California consider Newark - Oakland, New York John F Kennedy Intl - Oakland or New York LaGuardia - Oakland as they are the most popular.

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

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

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

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

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

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

    Currently, April is the cheapest month in which you can book a flight from Connecticut to Oakland, California (average of $183). Flying from Connecticut 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

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Alternative routes for Connecticut to Oakland

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

Discover the top airline that operate flights from Connecticut to Oakland. 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 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$359Average$540FlexibilityNo cancel feeOn-time63%

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