$188+ Cheap flights from Connecticut to Oakland, CA (OAK)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/6. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — OAK
Oct 24 — Oct 311
Round-trip
1 adult, Economy
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1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Connecticut to Oakland
Cheapest
Best
Last-minute
One-way
Cheapest flights from Connecticut to OaklandExplore 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 24, 2026.
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 24, 2026.
This Southwest deal was found by Cheapflights users on 9/22. 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 12/26:25 pm -
1 stop8h 10m
Tue 12/86:30 am -
1 stop6h 55m
Deal found 9/22![Southwest logo]()
$375
This Southwest deal was found by Cheapflights users on 9/23. 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 10/216:25 pm -
1 stop7h 55m
Wed 10/2811:55 pm -
1 stop8h 05m
Deal found 9/23![Southwest logo]()
$376
This Southwest deal was found by Cheapflights users on 9/19. 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.
Wed 10/1411:30 am -
2 stops10h 25m
Mon 10/1911:55 pm -
1 stop8h 00m
Deal found 9/19![Southwest logo]()
$418
This Southwest deal was found by Cheapflights users on 9/22. 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 11/2512:15 pm -
1 stop15h 05m
Tue 12/17:50 pm -
2 stops9h 05m
Deal found 9/22![Southwest logo]()
$428
This Southwest deal was found by Cheapflights users on 9/21. 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 10/237:05 pm -
1 stop8h 10m
Sun 10/2511:55 pm -
1 stop8h 05m
Deal found 9/21![Southwest logo]()
$436
This Southwest deal was found by Cheapflights users on 9/20. 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.
Sat 11/216:50 pm -
1 stop8h 25m
Fri 11/275:35 am -
1 stop7h 10m
Deal found 9/20![Southwest logo]()
$451
Best flights from Connecticut to OaklandDiscover carefully curated flight deals from Connecticut to Oakland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 24, 2026.
Discover carefully curated flight deals from Connecticut to Oakland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 24, 2026.
This Southwest deal was found by Cheapflights users on 9/22. 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 12/26:25 pm -
1 stop8h 10m
Tue 12/86:30 am -
1 stop6h 55m
Deal found 9/22![Southwest logo]()
$375
This Delta deal was found by Cheapflights users on 9/22. 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 12/57:10 am -
2 stops11h 57m
Sun 12/65:55 am -
2 stops11h 40m
Deal found 9/22![Delta logo]()
$587
This Southwest deal was found by Cheapflights users on 9/19. 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.
Wed 10/1411:30 am -
2 stops10h 25m
Mon 10/197:40 pm -
2 stops9h 35m
Deal found 9/19![Southwest logo]()
$423
This Southwest deal was found by Cheapflights users on 9/20. 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.
Sat 11/216:50 pm -
1 stop8h 25m
Fri 11/275:35 am -
1 stop7h 10m
Deal found 9/20![Southwest logo]()
$451
This Southwest deal was found by Cheapflights users on 9/20. 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.
Thu 12/246:25 pm -
1 stop8h 05m
Mon 12/2811:50 pm -
1 stop8h 00m
Deal found 9/20![Southwest logo]()
$478
This Southwest deal was found by Cheapflights users on 9/23. 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 11/208:25 am -
2 stops10h 15m
Mon 11/306:35 pm -
2 stops10h 20m
Deal found 9/23![Southwest logo]()
$515
This Southwest deal was found by Cheapflights users on 9/20. 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.
Mon 12/2112:15 pm -
1 stop15h 00m
Tue 12/2911:50 pm -
1 stop8h 00m
Deal found 9/20![Southwest logo]()
$531
This Southwest deal was found by Cheapflights users on 9/22. 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 11/2512:15 pm -
2 stops10h 25m
Tue 12/17:50 pm -
2 stops9h 05m
Deal found 9/22![Southwest logo]()
$577
Last-minute flights from Connecticut to OaklandDiscover last-minute flight deals from Connecticut to Oakland. Data last updated September 24, 2026 and is based on user searches.
Discover last-minute flight deals from Connecticut to Oakland. Data last updated September 24, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 9/20. 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 10/73:10 pm -
1 stop10h 00m
Mon 10/127:40 pm -
2 stops9h 35m
Deal found 9/20![Southwest logo]()
$514
This Kiwi.com deal was found by Cheapflights users on 9/21. 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.
Sun 10/116:05 am -
1 stop30h 00m
Wed 10/1412:47 pm -
2 stops22h 34m
Deal found 9/21![Multiple Airlines logo]()
$509
This Southwest deal was found by Cheapflights users on 9/19. 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.
Wed 10/1411:30 am -
2 stops10h 25m
Mon 10/1911:55 pm -
1 stop8h 00m
Deal found 9/19![Southwest logo]()
$418
This Kiwi.com deal was found by Cheapflights users on 9/21. 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.
Sun 10/186:05 am -
1 stop30h 00m
Thu 10/225:20 pm -
2 stops18h 01m
Deal found 9/21![Multiple Airlines logo]()
$477
This Southwest deal was found by Cheapflights users on 9/23. 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 10/216:25 pm -
1 stop7h 55m
Wed 10/2811:55 pm -
1 stop8h 05m
Deal found 9/23![Southwest logo]()
$376
This Southwest deal was found by Cheapflights users on 9/21. 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 10/237:05 pm -
1 stop8h 10m
Sun 10/2511:55 pm -
1 stop8h 05m
Deal found 9/21![Southwest logo]()
$436
One-way flights from Connecticut to OaklandSearch for one-way flight options from Connecticut to Oakland. Find affordable one-way fares based on user searches. Data last updated September 24, 2026.
Search for one-way flight options from Connecticut to Oakland. Find affordable one-way fares based on user searches. Data last updated September 24, 2026.
This Southwest deal was found by Cheapflights users on 9/19. 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.
Wed 1/65:05 pm -
1 stop8h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Southwest logo]()
$188
This Delta deal was found by Cheapflights users on 9/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/65:00 pm -
2 stops9h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Delta logo]()
$193
This Southwest deal was found by Cheapflights users on 9/21. 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 10/1411:30 am -
2 stops10h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Southwest logo]()
$194
This Southwest deal was found by Cheapflights users on 9/20. 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.
Thu 12/246:25 pm -
1 stop8h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Southwest logo]()
$205
This Southwest deal was found by Cheapflights users on 9/20. 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.
Sat 11/216:50 pm -
1 stop8h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Southwest logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 9/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/225:51 pm -
1 stop19h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Multiple Airlines logo]()
$227
This Southwest deal was found by Cheapflights users on 9/21. 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 11/195:40 am -
2 stops11h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Southwest logo]()
$230
This Southwest deal was found by Cheapflights users on 9/21. 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 11/16:40 pm -
1 stop8h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Southwest logo]()
$232
This Southwest deal was found by Cheapflights users on 9/23. 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 11/2012:55 pm -
1 stop14h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Southwest logo]()
$237
This Southwest deal was found by Cheapflights users on 9/22. 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 12/176:40 pm -
1 stop8h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Southwest logo]()
$242
This Kiwi.com deal was found by Cheapflights users on 9/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/116:05 am -
1 stop30h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Multiple Airlines logo]()
$245
Find 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 24, 2026.
Round-trip from | $375 (Southwest) |
|---|---|
One-way from | $188 (Southwest) |
Popular in | June |
Cheapest in | February |
Average price | $404 |
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 7,457,451 searches. Data last updated September 24, 2026.
Use the filters below to find and compare flights from Connecticut to Oakland that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
HartfordOakland
BDL Hartford Bradley Intl - OAK Oakland
BDLOAK
Hartford Bradley Intl
Wed 1/6
5:05 pm-10:45 pm
1 stop8h 40m
Oakland
Wed 12/31
12:00 am-3:00 am
Nonstop0h 00m
$188
HartfordOakland
BDL Hartford Bradley Intl - OAK Oakland
BDLOAK
Hartford Bradley Intl
Wed 1/6
5:00 pm-11:56 pm
2 stops9h 56m
Oakland
Wed 12/31
12:00 am-3:00 am
Nonstop0h 00m
$193
HartfordOakland
BDL Hartford Bradley Intl - OAK Oakland
BDLOAK
Hartford Bradley Intl
Sat 11/21
6:50 pm-12:15 am
1 stop8h 25m
Oakland
Wed 12/31
12:00 am-3:00 am
Nonstop0h 00m
$210
HartfordOakland
BDL Hartford Bradley Intl - OAK Oakland
BDLOAK
Hartford Bradley Intl
Fri 11/20
12:55 pm-12:40 am
1 stop14h 45m
Oakland
Wed 12/31
12:00 am-3:00 am
Nonstop0h 00m
$237
HartfordOakland
BDL Hartford Bradley Intl - OAK Oakland
BDLOAK
Hartford Bradley Intl
Wed 10/14
3:10 pm-10:10 pm
1 stop10h 00m
Oakland
Wed 12/31
12:00 am-3:00 am
Nonstop0h 00m
$260
HartfordOakland
BDL Hartford Bradley Intl - OAK Oakland
BDLOAK
Hartford Bradley Intl
Tue 9/29
5:13 pm-11:59 pm
2 stops9h 46m
Oakland
Wed 12/31
12:00 am-3:00 am
Nonstop0h 00m
$290
Quickest round-trip
HartfordOakland
BDL Hartford Bradley Intl - OAK Oakland
BDLOAK
Hartford Bradley Intl
Mon 9/28
6:20 pm-11:10 pm
1 stop7h 50m
Oakland
Wed 12/31
12:00 am-3:00 am
Nonstop0h 00m
$350
HartfordOakland
BDL Hartford Bradley Intl - OAK Oakland
BDLOAK
Hartford Bradley Intl
Wed 12/2
6:25 pm-11:35 pm
1 stop8h 10m
Oakland
Tue 12/8
6:30 am-4:25 pm
1 stop6h 55m
$375
HartfordOakland
BDL Hartford Bradley Intl - OAK Oakland
BDLOAK
Hartford Bradley Intl
Sat 11/7
2:00 pm-9:58 pm
2 stops10h 58m
Oakland
Wed 12/31
12:00 am-3:00 am
Nonstop0h 00m
$395
HartfordOakland
BDL Hartford Bradley Intl - OAK Oakland
BDLOAK
Hartford Bradley Intl
Sat 12/26
3:55 pm-12:35 am
1 stop11h 40m
Oakland
Wed 12/31
12:00 am-3:00 am
Nonstop0h 00m
$409
Showing 1-10 of 19 resultsSorted by cheapest first
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.
BDL-OAK
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
USCT-OAK
BDL-OAK
How much does it cost to fly round-trip from Connecticut to Oakland, California?
Airfare is below average for this route at the moment.
Connecticut to Oakland, California flights typically cost between $453 and $910 in December.The cheapest round-trip price found within the last 5 days was $375 on Southwest (Dec 2-Dec 8).
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.
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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.
Complete your trip
Complete your trip to Oakland by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Connecticut to Oakland by cabin class
Find flights from Connecticut to Oakland, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Oakland
Explore flights to Oakland departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 24, 2026.
Connecticut and Oakland flights
Browse other Connecticut and Oakland flight options. Last updated on September 24, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Connecticut to Oakland flights
Consider these flights traveling from Connecticut to Oakland.
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 7,457,451 searches. Data last updated September 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$384 | Average$537 | FlexibilityNo cancel fee | On-time63% |