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$186+ 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 8/10. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — YWG
Aug 7 — Aug 141
Fri 8/7
Fri 8/14
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 July 8, 2026.

This Kiwi.com deal was found by Cheapflights users on 7/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/109:55 am
LGA
-
YWG
1 stop6h 24m
Porter Airlines
Mon 9/1411:15 am
YWG
-
LGA
2 stops20h 40m
Porter Airlines
Deal found 7/7$365
This Kiwi.com deal was found by Cheapflights users on 7/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/109:55 am
LGA
-
YWG
1 stop6h 24m
Multiple Airlines
Mon 9/146:05 pm
YWG
-
LGA
1 stop13h 50m
Multiple Airlines
Deal found 7/7$369
This Kiwi.com deal was found by Cheapflights users on 7/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/49:55 am
LGA
-
YWG
1 stop24h 50m
Multiple Airlines
Wed 10/710:45 am
YWG
-
LGA
1 stop7h 40m
Multiple Airlines
Deal found 7/7$372
This Kiwi.com deal was found by Cheapflights users on 7/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/69:55 am
LGA
-
YWG
1 stop8h 20m
Multiple Airlines
Tue 10/1311:15 am
YWG
-
LGA
2 stops20h 40m
Multiple Airlines
Deal found 7/7$375
This Kiwi.com deal was found by Cheapflights users on 7/5. 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 8/68:55 am
EWR
-
YWG
2 stops30h 20m
Multiple Airlines
Wed 8/128:10 pm
YWG
-
EWR
1 stop11h 05m
Multiple Airlines
Deal found 7/5$386
This Kiwi.com deal was found by Cheapflights users on 7/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1710:40 am
EWR
-
YWG
1 stop8h 18m
Multiple Airlines
Tue 8/188:00 am
YWG
-
EWR
1 stop6h 45m
Multiple Airlines
Deal found 7/6$396
This Kiwi.com deal was found by Cheapflights users on 7/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/52:35 pm
EWR
-
YWG
1 stop24h 40m
Multiple Airlines
Wed 8/198:00 am
YWG
-
EWR
2 stops13h 00m
Multiple Airlines
Deal found 7/7$397
This Kiwi.com deal was found by Cheapflights users on 7/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/52:35 pm
EWR
-
YWG
1 stop24h 40m
Multiple Airlines
Tue 8/258:00 am
YWG
-
EWR
1 stop25h 40m
Multiple Airlines
Deal found 7/7$398
This Mytrip deal was found by Cheapflights users on 7/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/288:25 pm
LGA
-
YWG
1 stop13h 15m
Multiple Airlines
Sat 9/55:10 pm
YWG
-
LGA
1 stop14h 45m
Multiple Airlines
Deal found 7/7$399
This Kiwi.com deal was found by Cheapflights users on 7/3. 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 7/231:30 pm
EWR
-
YWG
1 stop21h 15m
Multiple Airlines
Mon 7/276:05 pm
YWG
-
EWR
1 stop16h 40m
Multiple Airlines
Deal found 7/3$399
This Kiwi.com deal was found by Cheapflights users on 7/5. 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 8/2110:40 am
EWR
-
YWG
1 stop28h 35m
Multiple Airlines
Sat 8/298:00 am
YWG
-
EWR
1 stop6h 45m
Multiple Airlines
Deal found 7/5$400
This Kiwi.com deal was found by Cheapflights users on 7/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/112:35 pm
EWR
-
YWG
1 stop24h 40m
Multiple Airlines
Tue 8/188:00 am
YWG
-
EWR
1 stop25h 40m
Multiple Airlines
Deal found 7/6$401

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 July 8, 2026.

Round-trip from

$365
(Kiwi.com)

One-way from

$186
(Kiwi.com)
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 July 8, 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

NewarkWinnipeg

EWR - YWG

EWRYWG

Newark

Fri 8/21

10:40 am-2:15 pm

1 stop28h 35m

Winnipeg

Sat 8/29

8:00 am-3:45 pm

1 stop6h 45m

$400

NewarkWinnipeg

EWR - YWG

EWRYWG

Newark

Fri 8/28

10:40 am-5:58 pm

1 stop8h 18m

Winnipeg

Sat 9/5

9:25 am-7:05 pm

1 stop8h 40m

$444

NewarkWinnipeg

EWR - YWG

EWRYWG

Newark

Fri 8/21

2:35 pm-2:15 pm

1 stop24h 40m

Winnipeg

Fri 8/28

9:25 am-9:40 pm

2 stops11h 15m

$447

New YorkWinnipeg

LGA - YWG

LGAYWG

New York LaGuardia

Tue 9/8

9:55 am-3:19 pm

1 stop6h 24m

Winnipeg

Fri 9/11

9:20 am-4:55 pm

1 stop6h 35m

$469

NewarkWinnipeg

EWR - YWG

EWRYWG

Newark

Wed 7/29

2:35 pm-12:55 am

2 stops11h 20m

Winnipeg

Sun 8/2

8:00 am-10:40 am

1 stop25h 40m

$483

New YorkWinnipeg

LGA - YWG

LGAYWG

New York LaGuardia

Fri 8/21

5:55 pm-2:15 pm

2 stops21h 20m

Winnipeg

Fri 8/28

9:25 am-4:55 pm

1 stop6h 30m

$484

New YorkWinnipeg

LGA - YWG

LGAYWG

New York LaGuardia

Fri 9/18

9:55 am-3:19 pm

1 stop6h 24m

Winnipeg

Tue 9/22

9:20 am-4:55 pm

1 stop6h 35m

$513

NewarkWinnipeg

EWR - YWG

EWRYWG

Newark

Mon 8/3

6:30 am-4:25 pm

1 stop10h 55m

Winnipeg

Mon 8/10

5:10 pm-8:10 am

1 stop14h 00m

$514

New YorkWinnipeg

LGA - YWG

LGAYWG

New York LaGuardia

Tue 10/20

6:00 am-12:37 pm

1 stop7h 37m

Winnipeg

Tue 10/20

3:20 pm-10:36 pm

1 stop6h 16m

$524

NewarkWinnipeg

EWR - YWG

EWRYWG

Newark

Sat 9/12

8:30 am-8:20 pm

2 stops12h 50m

Winnipeg

Sat 9/19

6:15 am-6:41 pm

2 stops11h 26m

$528

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/7

Showing 1-10 of 53 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 $469, 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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