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$199+ 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 7/7. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — YWG
Jun 11 — Jun 181
Thu 6/11
Thu 6/18
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 May 12, 2026.

This Mytrip deal was found by Cheapflights users on 5/11. 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.
Tue 6/95:55 pm
LGA
-
YWG
2 stops17h 48m
Porter Airlines
Tue 6/239:20 am
YWG
-
LGA
1 stop6h 35m
Porter Airlines
Deal found 5/11$420
This Trip.com deal was found by Cheapflights users on 5/11. 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 6/59:55 am
LGA
-
YWG
1 stop16h 00m
Multiple Airlines
Tue 6/99:20 am
YWG
-
LGA
1 stop6h 35m
Multiple Airlines
Deal found 5/11$435
This Mytrip deal was found by Cheapflights users on 5/11. 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.
Tue 6/95:55 pm
LGA
-
YWG
1 stop15h 45m
Multiple Airlines
Tue 6/239:25 am
YWG
-
LGA
1 stop9h 00m
Multiple Airlines
Deal found 5/11$437
This Trip.com deal was found by Cheapflights users on 5/9. 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.
Mon 6/155:55 pm
LGA
-
YWG
1 stop8h 00m
Multiple Airlines
Tue 6/239:20 am
YWG
-
LGA
1 stop6h 35m
Multiple Airlines
Deal found 5/9$438
This Trip.com deal was found by Cheapflights users on 5/8. 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.
Thu 6/49:55 am
LGA
-
YWG
1 stop16h 00m
Multiple Airlines
Wed 6/179:20 am
YWG
-
LGA
1 stop6h 35m
Multiple Airlines
Deal found 5/8$441
This Mytrip deal was found by Cheapflights users on 5/9. 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 6/267:55 pm
LGA
-
YWG
1 stop13h 45m
Multiple Airlines
Sun 7/125:10 pm
YWG
-
LGA
1 stop14h 45m
Multiple Airlines
Deal found 5/9$443
This Mytrip deal was found by Cheapflights users on 5/9. 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 6/263:55 pm
EWR
-
YWG
2 stops17h 45m
Multiple Airlines
Sun 7/125:10 pm
YWG
-
EWR
1 stop14h 04m
Multiple Airlines
Deal found 5/9$443
This Kiwi.com deal was found by Cheapflights users on 5/9. 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 6/125:55 pm
LGA
-
YWG
1 stop8h 00m
Multiple Airlines
Wed 6/179:25 am
YWG
-
LGA
1 stop6h 30m
Multiple Airlines
Deal found 5/9$444
This Kiwi.com deal was found by Cheapflights users on 5/10. 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 6/95:55 pm
LGA
-
YWG
1 stop8h 00m
Multiple Airlines
Tue 6/169:20 am
YWG
-
LGA
1 stop6h 35m
Multiple Airlines
Deal found 5/10$445
This Air Canada deal was found by Cheapflights users on 5/11. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:30 am
LGA
-
YWG
1 stop6h 34m
Air Canada
Tue 6/92:00 pm
YWG
-
LGA
1 stop5h 59m
Air Canada
Deal found 5/11$449
This Kiwi.com deal was found by Cheapflights users on 5/8. 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.
Sat 6/68:00 am
EWR
-
YWG
2 stops11h 03m
Multiple Airlines
Tue 6/2310:45 am
YWG
-
EWR
1 stop10h 00m
Multiple Airlines
Deal found 5/8$452
This Kiwi.com deal was found by Cheapflights users on 5/8. 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.
Sat 6/68:00 am
EWR
-
YWG
2 stops11h 03m
Multiple Airlines
Mon 6/156:15 am
YWG
-
EWR
1 stop12h 25m
Multiple Airlines
Deal found 5/8$453

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 May 12, 2026.

Round-trip from

$420
(Mytrip)

One-way from

$199
(United Airlines)
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 May 12, 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

Tue 6/9

3:25 pm-10:38 pm

1 stop8h 13m

Winnipeg

Tue 6/16

7:00 am-11:20 pm

1 stop15h 20m

$452

NewarkWinnipeg

EWR - YWG

EWRYWG

Newark

Mon 6/1

10:29 pm-10:10 pm

2 stops24h 41m

Winnipeg

Mon 6/29

7:45 am-7:40 pm

1 stop10h 55m

$462

New YorkWinnipeg

LGA - YWG

LGAYWG

New York LaGuardia

Wed 6/3

7:00 am-11:52 am

1 stop5h 52m

Winnipeg

Tue 6/9

7:00 am-11:30 pm

2 stops15h 30m

$462

New YorkWinnipeg

LGA - YWG

LGAYWG

New York LaGuardia

Wed 8/19

6:00 am-10:33 pm

2 stops17h 33m

Winnipeg

Tue 8/25

7:00 am-3:17 pm

1 stop7h 17m

$462

New YorkWinnipeg

LGA - YWG

LGAYWG

New York LaGuardia

Thu 10/1

9:55 am-3:19 pm

1 stop6h 24m

Winnipeg

Mon 10/5

9:20 am-4:55 pm

1 stop6h 35m

$465

New YorkWinnipeg

LGA - YWG

LGAYWG

New York LaGuardia

Sat 6/20

9:55 am-3:19 pm

1 stop6h 24m

Winnipeg

Tue 6/30

9:05 pm-4:55 pm

2 stops18h 50m

$482

New YorkWinnipeg

LGA - YWG

LGAYWG

New York LaGuardia

Tue 6/23

9:55 am-5:58 pm

2 stops9h 03m

Winnipeg

Fri 7/3

9:20 am-7:25 pm

1 stop9h 05m

$484

NewarkWinnipeg

EWR - YWG

EWRYWG

Newark

Sat 6/6

8:00 am-6:03 pm

2 stops11h 03m

Winnipeg

Mon 6/8

6:15 am-8:55 pm

2 stops13h 40m

$489

New YorkWinnipeg

LGA - YWG

LGAYWG

New York LaGuardia

Fri 6/5

9:55 am-3:19 pm

1 stop6h 24m

Winnipeg

Tue 6/9

9:20 am-4:55 pm

1 stop6h 35m

$496

New YorkWinnipeg

LGA - YWG

LGAYWG

New York LaGuardia

Mon 6/1

9:55 am-3:19 pm

1 stop6h 24m

Winnipeg

Mon 6/29

9:20 am-4:55 pm

1 stop6h 35m

$517

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/11

Showing 1-10 of 55 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 $465, United 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 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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