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$156+ 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 8/29. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — YWG
May 11 — May 181
Mon 5/11
Mon 5/18
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 April 11, 2026.

This Gotogate deal was found by Cheapflights users on 4/6. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/79:55 am
LGA
-
YWG
1 stop6h 24m
Multiple Airlines
Sat 5/162:00 pm
YWG
-
LGA
1 stop7h 36m
Multiple Airlines
Deal found 4/6$295
This Gotogate deal was found by Cheapflights users on 4/6. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/79:00 am
JFK
-
YWG
1 stop7h 14m
Air Canada
Sat 5/162:00 pm
YWG
-
JFK
1 stop7h 48m
Air Canada
Deal found 4/6$302
This Trip.com deal was found by Cheapflights users on 4/6. 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.
Fri 5/299:55 am
LGA
-
YWG
1 stop6h 24m
Porter Airlines
Tue 6/29:20 am
YWG
-
LGA
1 stop6h 35m
Porter Airlines
Deal found 4/6$310
This Trip.com deal was found by Cheapflights users on 4/6. 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.
Sat 5/309:55 am
LGA
-
YWG
1 stop6h 24m
Porter Airlines
Tue 6/29:20 am
YWG
-
LGA
1 stop6h 35m
Porter Airlines
Deal found 4/6$312
This Trip.com deal was found by Cheapflights users on 4/6. 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.
Thu 5/289:55 am
LGA
-
YWG
1 stop6h 24m
Porter Airlines
Tue 6/29:20 am
YWG
-
LGA
1 stop6h 35m
Porter Airlines
Deal found 4/6$314
This Trip.com deal was found by Cheapflights users on 4/8. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/29:55 am
LGA
-
YWG
1 stop6h 24m
Porter Airlines
Sun 5/109:20 am
YWG
-
LGA
1 stop6h 35m
Porter Airlines
Deal found 4/8$325
This Ticket deal was found by Cheapflights users on 4/6. 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 Ticket is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/710:35 am
LGA
-
YWG
1 stop5h 39m
Air Canada
Sat 5/165:10 am
YWG
-
LGA
2 stops15h 20m
Air Canada
Deal found 4/6$329
This Mytrip deal was found by Cheapflights users on 4/6. 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.
Fri 5/299:55 am
LGA
-
YWG
1 stop6h 24m
Porter Airlines
Mon 6/19:20 am
YWG
-
LGA
1 stop6h 35m
Porter Airlines
Deal found 4/6$333
This Kiwi.com deal was found by Cheapflights users on 4/8. 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.
Wed 4/299:55 am
LGA
-
YWG
1 stop6h 35m
Porter Airlines
Fri 5/19:20 am
YWG
-
LGA
1 stop6h 35m
Porter Airlines
Deal found 4/8$336
This Justfly.com deal was found by Cheapflights users on 4/6. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/305:55 pm
LGA
-
YWG
1 stop6h 40m
Porter Airlines
Sat 5/99:20 am
YWG
-
LGA
1 stop6h 35m
Porter Airlines
Deal found 4/6$338
This Gotogate deal was found by Cheapflights users on 4/7. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/275:55 pm
LGA
-
YWG
1 stop6h 40m
Porter Airlines
Sun 11/112:10 pm
YWG
-
LGA
1 stop6h 10m
Porter Airlines
Deal found 4/7$340
This Mytrip deal was found by Cheapflights users on 4/6. 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.
Thu 5/79:10 am
EWR
-
YWG
1 stop8h 15m
Multiple Airlines
Sat 5/166:15 am
YWG
-
EWR
1 stop7h 55m
Multiple Airlines
Deal found 4/6$375

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 April 11, 2026.

Round-trip from

$295
(Gotogate)

One-way from

$156
(oojo)
From Connecticut to Winnipeg
Search Deals
One-way flight from Connecticut to Winnipeg
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 April 11, 2026.
Use the filters below to find and compare flights from Connecticut to Winnipeg that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

New YorkWinnipeg

LGA - YWG

LGAYWG

New York LaGuardia

Fri 5/29

9:55 am-3:19 pm

1 stop6h 24m

Winnipeg

Mon 6/1

9:20 am-4:55 pm

1 stop6h 35m

$333

New YorkWinnipeg

LGA - YWG

LGAYWG

New York LaGuardia

Mon 6/1

9:55 am-3:19 pm

1 stop6h 24m

Winnipeg

Sat 6/6

9:20 am-4:55 pm

1 stop6h 35m

$360

New YorkWinnipeg

LGA - YWG

LGAYWG

New York LaGuardia

Thu 5/7

7:55 am-2:55 pm

1 stop8h 00m

Winnipeg

Sat 5/16

5:41 pm-11:44 pm

1 stop5h 03m

$369

New YorkWinnipeg

LGA - YWG

LGAYWG

New York LaGuardia

Thu 5/21

6:00 am-2:55 pm

1 stop9h 55m

Winnipeg

Thu 5/28

3:50 pm-11:44 pm

1 stop6h 54m

$370

New YorkWinnipeg

LGA - YWG

LGAYWG

New York LaGuardia

Mon 6/15

6:05 am-3:04 pm

1 stop9h 59m

Winnipeg

Wed 7/8

12:46 pm-11:43 pm

1 stop9h 57m

$388

New YorkWinnipeg

LGA - YWG

LGAYWG

New York LaGuardia

Mon 6/15

6:05 am-3:04 pm

1 stop9h 59m

Winnipeg

Tue 7/7

12:46 pm-11:43 pm

1 stop9h 57m

$388

New YorkWinnipeg

LGA - YWG

LGAYWG

New York LaGuardia

Mon 6/15

6:05 am-3:04 pm

1 stop9h 59m

Winnipeg

Fri 7/10

3:59 pm-9:57 pm

1 stop4h 58m

$388

New YorkWinnipeg

JFK - YWG

JFKYWG

New York John F Kennedy Intl

Sat 6/20

7:15 am-3:19 pm

1 stop9h 04m

Winnipeg

Fri 7/10

3:59 pm-11:55 pm

1 stop6h 56m

$388

New YorkWinnipeg

LGA - YWG

LGAYWG

New York LaGuardia

Sat 5/30

9:55 am-3:19 pm

1 stop6h 24m

Winnipeg

Tue 6/2

9:05 pm-11:14 pm

2 stops25h 09m

$393

New YorkWinnipeg

LGA - YWG

LGAYWG

New York LaGuardia

Thu 4/30

9:55 am-3:30 pm

1 stop6h 35m

Winnipeg

Mon 5/4

9:20 am-4:55 pm

1 stop6h 35m

$393

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/6

Showing 1-10 of 54 resultsSorted by cheapest first
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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 $333, Porter Airlines can have you in Winnipeg from Connecticut in 6h 24m. 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 New York John F Kennedy Intl - Winnipeg or New York LaGuardia - Winnipeg, Newark - 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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