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$85+ Cheap flights from Connecticut to Winnipeg (YWG)

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 1/25. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — YWG
Dec 21 — Dec 281
Sun 12/21
Sun 12/28
1 adult, Economy
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Find flight deals from Connecticut to Winnipeg

Cheapest flights from Connecticut to Winnipeg
Explore the most affordable flight options available from Connecticut to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 21, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/20. 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.
Wed 12/36:20 amLGA - YWG
1 stop9h 47mMultiple Airlines
Mon 12/89:00 pmYWG - LGA
2 stops18h 29mMultiple Airlines
Deal found 11/20$221
This Kiwi.com deal was found by Cheapflights users on 11/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/95:59 amEWR - YWG
2 stops19h 42mMultiple Airlines
Thu 12/118:20 pmYWG - EWR
1 stop10h 55mMultiple Airlines
Deal found 11/19$273
This Kiwi.com deal was found by Cheapflights users on 11/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/76:15 amJFK - YWG
1 stop9h 52mMultiple Airlines
Fri 12/1212:55 pmYWG - JFK
2 stops35h 04mMultiple Airlines
Deal found 11/18$282
This Kiwi.com deal was found by Cheapflights users on 11/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/75:15 amEWR - YWG
1 stop10h 52mMultiple Airlines
Fri 12/127:30 amYWG - EWR
2 stops15h 22mMultiple Airlines
Deal found 11/18$288
This Kiwi.com deal was found by Cheapflights users on 11/20. 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.
Tue 12/96:20 amLGA - YWG
2 stops19h 21mMultiple Airlines
Thu 12/1112:10 pmYWG - LGA
1 stop8h 15mMultiple Airlines
Deal found 11/20$304
This Kiwi.com deal was found by Cheapflights users on 11/20. 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.
Tue 12/210:30 pmEWR - YWG
1 stop17h 37mMultiple Airlines
Sat 12/66:45 amYWG - EWR
2 stops17h 44mMultiple Airlines
Deal found 11/20$320
This Trip.com deal was found by Cheapflights users on 11/18. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/76:20 amLGA - YWG
1 stop9h 47mMultiple Airlines
Fri 12/1212:10 pmYWG - LGA
1 stop8h 15mMultiple Airlines
Deal found 11/18$321
This Kiwi.com deal was found by Cheapflights users on 11/20. 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.
Thu 12/259:55 amLGA - YWG
1 stop6h 35mMultiple Airlines
Wed 1/147:30 amYWG - LGA
1 stop7h 59mMultiple Airlines
Deal found 11/20$336
This Kiwi.com deal was found by Cheapflights users on 11/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/306:00 amJFK - YWG
1 stop10h 07mMultiple Airlines
Sat 12/69:00 pmYWG - JFK
2 stops26h 59mMultiple Airlines
Deal found 11/19$359
This Kiwi.com deal was found by Cheapflights users on 11/20. 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.
Mon 12/11:00 pmJFK - YWG
2 stops36h 41mMultiple Airlines
Mon 12/88:00 amYWG - JFK
1 stop20h 30mMultiple Airlines
Deal found 11/20$371
This Kiwi.com deal was found by Cheapflights users on 11/20. 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.
Fri 12/126:15 amJFK - YWG
1 stop9h 52mMultiple Airlines
Sat 12/138:20 pmYWG - JFK
1 stop22h 43mMultiple Airlines
Deal found 11/20$373
This Kiwi.com deal was found by Cheapflights users on 11/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/99:55 amLGA - YWG
1 stop6h 35mPorter Airlines
Thu 12/1112:10 pmYWG - LGA
1 stop8h 15mPorter Airlines
Deal found 11/19$375

Cheap flight deals from Connecticut to Winnipeg

Keep the following information in mind while searching for Connecticut to Winnipeg flight deals. Data was last updated November 21, 2025.

Round-trip from

$221
(Kiwi.com)

One-way from

$85
(Trip.com)

Popular in

November

Cheapest in

October

Average price

$1,315
From Connecticut to Winnipeg
Search Deals
One-way flight from Connecticut to Winnipeg
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($63 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($45 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Connecticut to Winnipeg 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 21, 2025.
Use the filters below to find and compare flights from Connecticut to Winnipeg that are best for you.

Fly from

Connecticut

Fly to

Winnipeg

Route

Depart

Return

Price

New YorkWinnipeg

LGA - YWG

LGAYWG

New York LaGuardia

Mon 1/12

6:00 am-6:03 pm

1 stop13h 03m

Winnipeg

Thu 2/19

6:15 am-11:05 pm

2 stops15h 50m

$258

NewarkWinnipeg

EWR - YWG

EWRYWG

Newark

Wed 3/4

5:55 am-3:09 pm

1 stop10h 14m

Winnipeg

Fri 3/6

6:15 am-9:35 pm

2 stops14h 20m

$269

New YorkWinnipeg

LGA - YWG

LGAYWG

New York LaGuardia

Wed 3/4

6:20 am-3:09 pm

1 stop9h 49m

Winnipeg

Fri 3/6

7:30 am-11:14 pm

1 stop14h 44m

$280

New YorkWinnipeg

LGA - YWG

LGAYWG

New York LaGuardia

Tue 12/9

6:20 am-12:41 am

2 stops19h 21m

Winnipeg

Thu 12/11

12:10 pm-9:25 pm

1 stop8h 15m

$282

New YorkWinnipeg

JFK - YWG

JFKYWG

New York John F Kennedy Intl

Sun 12/7

6:15 am-3:07 pm

1 stop9h 52m

Winnipeg

Fri 12/12

12:55 pm-12:59 am

2 stops35h 04m

$282

NewarkWinnipeg

EWR - YWG

EWRYWG

Newark

Sun 12/7

5:15 am-3:07 pm

1 stop10h 52m

Winnipeg

Fri 12/12

7:30 am-11:52 pm

2 stops15h 22m

$288

NewarkWinnipeg

EWR - YWG

EWRYWG

Newark

Mon 1/12

5:30 am-12:41 am

2 stops20h 11m

Winnipeg

Thu 2/19

6:15 am-11:30 pm

2 stops16h 15m

$301

NewarkWinnipeg

EWR - YWG

EWRYWG

Newark

Tue 12/2

10:30 pm-3:07 pm

1 stop17h 37m

Winnipeg

Sat 12/6

6:45 am-1:29 am

2 stops17h 44m

$320

New YorkWinnipeg

LGA - YWG

LGAYWG

New York LaGuardia

Sun 12/7

6:20 am-3:07 pm

1 stop9h 47m

Winnipeg

Fri 12/12

12:10 pm-9:25 pm

1 stop8h 15m

$321

NewarkWinnipeg

EWR - YWG

EWRYWG

Newark

Tue 12/9

5:15 am-12:41 am

2 stops20h 26m

Winnipeg

Thu 12/11

8:20 pm-10:55 am

2 stops13h 35m

$326

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

Showing 1-10 of 42 results
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Best time to book a flight from Connecticut to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg 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 Winnipeg
No data available for this route at this time. Please check back soon.

Related info for your journey

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

    If you book a flight to Winnipeg from Connecticut, you will be flying to Winnipeg, which is the city’s only airport. Winnipeg (YWG) is located 4.6 mi from the center of Winnipeg.

  • What are the cheapest airlines to fly from Connecticut to Winnipeg one-way?

    One-way options have recently been found by users for as low as $164 on Porter Airlines. Other airlines that offer cheap prices include Air Canada from $184 and United Airlines from $189 one-way.

  • What are the most popular routes from Connecticut to Winnipeg?

    While some choose either New York LaGuardia - Winnipeg or Newark - Winnipeg, New York John F Kennedy Intl - Winnipeg is the most popular route from Connecticut to Winnipeg.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Connecticut to Winnipeg by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Portage la Prairie

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Top airline flying from Connecticut to Winnipeg

Discover the top airline that operate flights from Connecticut to Winnipeg. 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 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$733Average$851FlexibilityNo cancel feeOn-timeN/A

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