Find Cheap Flights from Winnipeg to Orlando (YWG - ORL)

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Wed 1/17
Wed 1/24
Any month
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Good to Know

Low Season:
May
Best time to beat the crowds
3%
expected price decrease
High Season:
December
Most popular time to fly
11%
expected price increase
Average Price:
$494
(avg. price over the last 2 weeks)
Good Deal:
$369
or less (round trip)

When to Book Flights from Winnipeg to Orlando

Average price per month
Flight prices as travel date approaches
-1 day
-2 days

Top tips for Finding a Cheap Flight

Looking for a cheap flight? 25% of our users found flights on this route for $369 or less.
The cheapest flight from Winnipeg to Orlando was found 1 day before departure, on average.
Book at least 1 week before departure in order to get a below-average price.
Morning departure is around 2% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Book cheap flights from Winnipeg to Orlando (round-trip)

Airports
Origin
Winnipeg
$280
only
$280
Destination
Orlando
$280
only
$280
Wed, May 16
YWG
MCO
7h 51m
Wed, May 30
MCO
YWG
6h 10m
Trip: 15 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
CUN
MSY
Good 7.0

The outbound crew was terrific. The flight itself was fine. We even arrived early.

Upon deplaning in Cancun, ALL passengers are put on a bus and driven far away from the terminals to an arrivals area. Those of us with connecting flights are royally f*cked at that point, especially if your connection is short, as mine was. The so-called shuttle to the departure terminals, which are entire kilometers away, was to arrive in like half an hour. HALF AN HOUR. Who has this time to spare?? The alternative to the shuttle is paying a taxi that charges a hefty fare--and God help you if you don't have cash. The departures terminal was swamped and only thru begging assistance and line cuts did I make my connection...and then only by the skin of my teeth. It was a complete nightmare.

MSY
JFK
Excellent 10.0

The overhead bin did not stay down low enough so that I could place my bag in. It would lower then before I could place my bag raise slightly by a few inches. For someone of my height (5’5”) that was problematic. Fortunately another passenger saw my dilemma and held the bin lower to its full opening capacity. This also momentarily slowed down the boarding process.

LAX
CUN
Mediocre 2.6

Terrible customer service both on the phone before the flight, but Especially from the gate agent. Wow she was really horrible.

The flight attendants on board were good! They helped get everything straight. Easily could have been handled by the incompetent gate agent. Wow.

SAN
LAX
Excellent 10.0

on time

BOS
MKE
Excellent 10.0

Direct flight, on time, friendly crew, smooth flight

Sun, Feb 11
YWG
MCO
11h 52m
Wed, Feb 14
MCO
YWG
8h 58m
Trip: 4 days
7.1GoodShow reviews
Overall 7.1 Good
Based on 20922 reviews
Overall
7.2
Boarding
7.3
Comfort
7.0
Crew
7.7
Entertainment
6.9
Food
6.4
YYC
LHR
Mediocre 3.6

Mix up with seating had boarding card reprinted twice and no one could explain why it happened. Staff otherwise were good.

ATL
YYZ
Okay 5.6

It was quite and smooth

I have never been so hot on a plane. Even with the air blowing on me I was sweating! It was crazy hot!

YEG
YVR
Excellent 10.0

the staff very helpful , respectful, didn't feel rush they had their attention on helping me .Very grateful Thank you all

YHZ
YUL
Excellent 8.6

Everything went very smoothly with this flight. It boarded on time. The crew were all very friendly. I enjoyed the entertainment selections and found a tv show that I had been wanting to see. I managed to watch 2 episodes and look forward to watching more of the same show on my flight back. I ended up having the 2 seats to myself which was great. Extra legroom. I have no complaints at all.

LHR
YYC
Good 6.0

Food is tasteless and it is too crapped. No leg room on planes

Sun, Feb 11
YWG
MCO
13h 30m
Wed, Feb 14
MCO
YWG
9h 28m
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Sat, Jan 20
YWG
MCO
4h 00m
Sat, Feb 3
MCO
YWG
4h 15m
Trip: 15 days
7.1GoodShow reviews
Overall 7.1 Good
Based on 52 reviews
Boarding
7.2
Comfort
7.1
Crew
7.5
Entertainment
6.7
Food
7.0
YYZ
MBJ
Excellent 9.3

Great flight. Smooth and comfortable!

Entertainment system needs updating

MZT
YVR
Good 6.0

I got to come back home! The fly was delayed due to a technical issue that required a part to be sourced. Unfortunately, the part was not available in the local shop (YVR-Vancouver) Instead they had to fly the part to be replaced from (YYZ-Toronto) The good fortune for us is that the hotel did allow us to use their facilities and enjoy their F&B all with the exception of a room to lay. They allowed pools and lounge chairs which is just as well. I am not trying to be critical but have the delayed occur while we were at the Airport-It would have been a killer way to close a vacation! Check-in agent was superb. She was very helpful and understanding and really a super star

Lack of information by local agents either by the design or just by being left in the dark. The Airport staff was not knowledgeable either they were very sympathetic and accommodating (more so than the Nexus-Local Agents) I am sure is beyond their power and is not something they have power or control over. It was bad luck! I would hate to be the incoming passengers as it meant they lost a whole afternoon.

MCO
YYZ
Excellent 8.0

Cheap fast on time seats tight but comfy

Rare smiles from sun wings employer waited until 2 hours before flights departure before the employees were at the airfport for checking really tight seats

PVR
YWG
Excellent 9.6

Inflight staff very courteous

Flight arrived late

MCO
YYZ
Good 7.0

Baggage should be included in the price. You should be able to choose your seats and preboard on the internet.

Sun, Feb 11
YWG
MCO
11h 52m
Wed, Feb 14
MCO
YWG
11h 47m
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Sun, Mar 4
YWG
MCO
8h 11m
Wed, Mar 7
MCO
YWG
8h 40m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SEA
ANC
Excellent 10.0

Alaska Airlines is way overpriced and way less comfortable than Delta. I’m a Delta loyalist forever now!

Nothing.

TUS
SEA
Excellent 10.0

Delta did a really good job as always. Cheaper, more comfortable, and a WAY better experience than Alaska Airlines.

Nothing.

MSY
JFK
Excellent 10.0

The overhead bin did not stay down low enough so that I could place my bag in. It would lower then before I could place my bag raise slightly by a few inches. For someone of my height (5’5”) that was problematic. Fortunately another passenger saw my dilemma and held the bin lower to its full opening capacity. This also momentarily slowed down the boarding process.

JFK
CMH
Excellent 9.6

Always nice to be on an American plane out of an American airport.....SO much more professional. :))

YUL
DTW
Mediocre 2.0

Not applied

Not applied

Sun, Mar 18
YWG
MCO
11h 02m
Sun, Mar 25
MCO
YWG
17h 17m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Sat, Jan 27
YWG
MCO
7h 17m
Sat, Feb 3
MCO
YWG
8h 50m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LAX
CUN
Mediocre 2.6

Terrible customer service both on the phone before the flight, but Especially from the gate agent. Wow she was really horrible.

The flight attendants on board were good! They helped get everything straight. Easily could have been handled by the incompetent gate agent. Wow.

SYR
JFK
Good 7.0

Nothing Special

CUN
MSY
Good 7.0

The outbound crew was terrific. The flight itself was fine. We even arrived early.

Upon deplaning in Cancun, ALL passengers are put on a bus and driven far away from the terminals to an arrivals area. Those of us with connecting flights are royally f*cked at that point, especially if your connection is short, as mine was. The so-called shuttle to the departure terminals, which are entire kilometers away, was to arrive in like half an hour. HALF AN HOUR. Who has this time to spare?? The alternative to the shuttle is paying a taxi that charges a hefty fare--and God help you if you don't have cash. The departures terminal was swamped and only thru begging assistance and line cuts did I make my connection...and then only by the skin of my teeth. It was a complete nightmare.

SEA
ANC
Excellent 10.0

Alaska Airlines is way overpriced and way less comfortable than Delta. I’m a Delta loyalist forever now!

Nothing.

YUL
DTW
Mediocre 2.0

Not applied

Not applied

Sat, Mar 31
YWG
MCO
4h 00m
Sat, Apr 7
MCO
YWG
4h 15m
Trip: 8 days
7.1GoodShow reviews
Overall 7.1 Good
Based on 52 reviews
Boarding
7.2
Comfort
7.1
Crew
7.5
Entertainment
6.7
Food
7.0
PVR
YWG
Excellent 9.6

Inflight staff very courteous

Flight arrived late

MBJ
YYZ
Excellent 8.0

First check-in luggage is free

No free snacks

CUN
YEG
Excellent 8.0

Small Seating. Unable to pre-check in.

MCO
YYZ
Good 7.0

Baggage should be included in the price. You should be able to choose your seats and preboard on the internet.

MCO
YYZ
Mediocre 2.0

Our flight changed without warning 2 weeks before from a direct flight to a non-direct flight. Unable to get money back for upgrade or flight.

Sun, Feb 11
YWG
MCO
13h 30m
Sun, Feb 18
MCO
YWG
6h 45m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SEA
ANC
Excellent 10.0

Alaska Airlines is way overpriced and way less comfortable than Delta. I’m a Delta loyalist forever now!

Nothing.

TUS
SEA
Excellent 10.0

Delta did a really good job as always. Cheaper, more comfortable, and a WAY better experience than Alaska Airlines.

Nothing.

JFK
CMH
Excellent 9.6

Always nice to be on an American plane out of an American airport.....SO much more professional. :))

SYR
JFK
Good 7.0

Nothing Special

MSY
JFK
Excellent 10.0

The overhead bin did not stay down low enough so that I could place my bag in. It would lower then before I could place my bag raise slightly by a few inches. For someone of my height (5’5”) that was problematic. Fortunately another passenger saw my dilemma and held the bin lower to its full opening capacity. This also momentarily slowed down the boarding process.

Sat, Feb 3
YWG
MCO
4h 00m
Sat, Feb 17
MCO
YWG
4h 15m
Trip: 15 days
7.1GoodShow reviews
Overall 7.1 Good
Based on 52 reviews
Boarding
7.2
Comfort
7.1
Crew
7.5
Entertainment
6.7
Food
7.0
MBJ
YYZ
Excellent 8.0

First check-in luggage is free

No free snacks

PIE
YYZ
Good 7.0

I liked sitting by the Emergency exit so I had more legroom.

Did not like the small bag allowance for carry on and the fact that we were charged an extra $25 because our carry-ones were over 5 kilos. That is a ridiculously small allowance and just a cash grab for the airline!

PVR
YWG
Excellent 9.6

Inflight staff very courteous

Flight arrived late

MCO
YYZ
Excellent 8.6

They only take credit cards for payment. No debit or cash.

MCO
YYZ
Good 7.0

Baggage should be included in the price. You should be able to choose your seats and preboard on the internet.

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Winnipeg to Orlando Flight Information

Avg. Flight Duration 4h 07m
Flights Arrive in Orlando
Flights Depart from Winnipeg
Flight Price $280
Distance 1695 miles
Airlines Delta, Air Canada, Sunwing Airlines