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$69+ 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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — YWG
Jan 1 — Jan 81
Thu 1/1
Thu 1/8
1 adult, Economy
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Cheap 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 December 2, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/1. 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 12/125:15 amEWR - YWG
1 stop10h 52mMultiple Airlines
Sun 12/147:30 amYWG - EWR
1 stop16h 40mMultiple Airlines
Deal found 12/1$233
This Kiwi.com deal was found by Cheapflights users on 11/30. 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 12/55:15 amEWR - YWG
1 stop10h 52mMultiple Airlines
Mon 12/89:00 pmYWG - EWR
2 stops23h 35mMultiple Airlines
Deal found 11/30$247
This Kiwi.com deal was found by Cheapflights users on 12/1. 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 12/210:00 amJFK - YWG
1 stop30h 07mMultiple Airlines
Mon 12/89:00 pmYWG - JFK
2 stops14h 00mMultiple Airlines
Deal found 12/1$253
This Kiwi.com deal was found by Cheapflights users on 11/30. 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 12/56:20 amLGA - YWG
1 stop9h 47mMultiple Airlines
Mon 12/89:00 pmYWG - LGA
2 stops18h 29mMultiple Airlines
Deal found 11/30$298
This Mytrip deal was found by Cheapflights users on 12/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/810:00 pmEWR - YWG
2 stops26h 50mMultiple Airlines
Wed 12/107:30 amYWG - EWR
1 stop12h 01mMultiple Airlines
Deal found 12/1$298
This Kiwi.com deal was found by Cheapflights users on 11/30. 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 12/56:15 amJFK - YWG
1 stop9h 52mMultiple Airlines
Mon 12/89:00 pmYWG - JFK
2 stops14h 00mMultiple Airlines
Deal found 11/30$298
This Kiwi.com deal was found by Cheapflights users on 12/1. 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 12/28:30 pmLGA - YWG
1 stop19h 37mMultiple Airlines
Mon 12/89:00 pmYWG - LGA
2 stops18h 29mMultiple Airlines
Deal found 12/1$301
This Kiwi.com deal was found by Cheapflights users on 12/1. 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
Mon 12/89:00 pmYWG - EWR
2 stops27h 10mMultiple Airlines
Deal found 12/1$301
This Kiwi.com deal was found by Cheapflights users on 12/1. 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 12/56:20 amLGA - YWG
1 stop9h 47mMultiple Airlines
Sun 12/77:30 amYWG - LGA
1 stop26h 59mMultiple Airlines
Deal found 12/1$303
This Kiwi.com deal was found by Cheapflights users on 12/1. 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 12/55:59 amEWR - YWG
1 stop10h 08mMultiple Airlines
Sun 12/77:30 amYWG - EWR
1 stop23h 18mMultiple Airlines
Deal found 12/1$305
This Kiwi.com deal was found by Cheapflights users on 11/30. 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 12/168:30 pmLGA - YWG
1 stop19h 37mMultiple Airlines
Tue 12/236:00 amYWG - LGA
1 stop9h 55mMultiple Airlines
Deal found 11/30$308
This Mytrip deal was found by Cheapflights users on 11/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/1510:00 pmEWR - YWG
3 stops25h 41mMultiple Airlines
Mon 12/228:00 amYWG - EWR
1 stop14h 59mMultiple Airlines
Deal found 11/30$330

Find flight deals from Connecticut to Winnipeg

Keep the following information in mind while searching for Connecticut to Winnipeg flight deals. Data was last updated December 2, 2025.

Round-trip from

$233
(Kiwi.com)

One-way from

$69
(Trip.com)

Popular in

November

Cheapest in

October

Average price

$1,093
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 December 2025
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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 December 2, 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

NewarkWinnipeg

EWR - YWG

EWRYWG

Newark

Fri 12/12

5:15 am-3:07 pm

1 stop10h 52m

Winnipeg

Sun 12/14

7:30 am-1:10 am

1 stop16h 40m

$233

New YorkWinnipeg

LGA - YWG

LGAYWG

New York LaGuardia

Fri 1/16

6:29 am-3:07 pm

1 stop9h 38m

Winnipeg

Fri 1/23

6:45 am-9:29 pm

2 stops37h 44m

$263

New YorkWinnipeg

LGA - YWG

LGAYWG

New York LaGuardia

Fri 2/6

6:20 am-3:09 pm

1 stop9h 49m

Winnipeg

Sun 2/8

7:30 am-9:29 pm

1 stop12h 59m

$266

New YorkWinnipeg

LGA - YWG

LGAYWG

New York LaGuardia

Thu 1/8

9:55 am-3:30 pm

1 stop6h 35m

Winnipeg

Mon 1/12

12:10 pm-8:00 pm

1 stop6h 50m

$292

NewarkWinnipeg

EWR - YWG

EWRYWG

Newark

Thu 1/8

3:45 pm-12:42 am

2 stops9h 57m

Winnipeg

Mon 1/12

8:00 am-9:14 pm

1 stop12h 14m

$304

NewarkWinnipeg

EWR - YWG

EWRYWG

Newark

Fri 1/16

5:25 am-3:07 pm

1 stop10h 42m

Winnipeg

Fri 1/23

6:15 am-7:46 pm

2 stops12h 31m

$310

NewarkWinnipeg

EWR - YWG

EWRYWG

Newark

Tue 4/7

5:45 am-12:39 am

2 stops19h 54m

Winnipeg

Tue 4/14

4:25 pm-9:15 am

2 stops15h 50m

$337

NewarkWinnipeg

EWR - YWG

EWRYWG

Newark

Tue 1/6

8:30 pm-11:13 am

2 stops15h 43m

Winnipeg

Fri 1/9

4:25 pm-10:55 am

2 stops17h 30m

$338

New YorkWinnipeg

LGA - YWG

LGAYWG

New York LaGuardia

Mon 12/15

6:00 am-6:03 pm

1 stop13h 03m

Winnipeg

Mon 12/22

8:00 am-11:37 pm

1 stop14h 37m

$339

New YorkWinnipeg

LGA - YWG

LGAYWG

New York LaGuardia

Mon 1/12

9:55 am-3:30 pm

1 stop6h 35m

Winnipeg

Fri 1/16

12:10 pm-8:00 pm

1 stop6h 50m

$346

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/29

Showing 1-10 of 46 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.

  • How long is the flight from Connecticut to Winnipeg?

    For as low as $292, Porter Airlines can have you in Winnipeg from Connecticut in 6h 35m. Airlines will cover a distance of 1289 mi. This flight may include one or multiple stops.

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

    While some choose either Newark - Winnipeg or New York LaGuardia - 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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