Flights To Osceola County - Cheap Flights Starting at CA $65

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How Much Does it Cost To Fly To Osceola County?

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Thu, Jan 21 - Thu, Jan 28
HVN
Tweed - New Haven Regional
MCO
Orlando Intl.
CA $160 Roundtrip, found 2 days ago
CA $160
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Jan 21 from Tweed - New Haven Regional to Orlando Intl., returning Thu, Jan 28, priced at CA $160 found 2 days ago
Thu, Jun 4 - Sat, Jun 6
HVN
Tweed - New Haven Regional
MCO
Orlando Intl.
CA $182 Roundtrip, found 2 days ago
CA $182
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Jun 4 from Tweed - New Haven Regional to Orlando Intl., returning Sat, Jun 6, priced at CA $182 found 2 days ago
Tue, Jun 9 - Sun, Jun 14
HVN
Tweed - New Haven Regional
MCO
Orlando Intl.
CA $185 Roundtrip, found 3 days ago
CA $185
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Tue, Jun 9 from Tweed - New Haven Regional to Orlando Intl., returning Sun, Jun 14, priced at CA $185 found 3 days ago
Sun, May 31 - Tue, Jun 2
HVN
Tweed - New Haven Regional
MCO
Orlando Intl.
CA $192 Roundtrip, found 3 days ago
CA $192
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sun, May 31 from Tweed - New Haven Regional to Orlando Intl., returning Tue, Jun 2, priced at CA $192 found 3 days ago
Sun, Aug 23 - Tue, Aug 25
HVN
Tweed - New Haven Regional
MCO
Orlando Intl.
CA $200 Roundtrip, found 5 days ago
CA $200
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sun, Aug 23 from Tweed - New Haven Regional to Orlando Intl., returning Tue, Aug 25, priced at CA $200 found 5 days ago
Thu, Jan 21 - Fri, Jan 29
HVN
Tweed - New Haven Regional
MCO
Orlando Intl.
CA $201 Roundtrip, found 2 days ago
CA $201
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Jan 21 from Tweed - New Haven Regional to Orlando Intl., returning Fri, Jan 29, priced at CA $201 found 2 days ago
Wed, Jun 17 - Sun, Jun 21
HVN
Tweed - New Haven Regional
MCO
Orlando Intl.
CA $211 Roundtrip, found 3 days ago
CA $211
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Wed, Jun 17 from Tweed - New Haven Regional to Orlando Intl., returning Sun, Jun 21, priced at CA $211 found 3 days ago
Sun, Aug 23 - Tue, Aug 25
HVN
Tweed - New Haven Regional
MCO
Orlando Intl.
CA $212 Roundtrip, found 5 days ago
CA $212
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sun, Aug 23 from Tweed - New Haven Regional to Orlando Intl., returning Tue, Aug 25, priced at CA $212 found 5 days ago
Wed, Nov 4 - Tue, Nov 10
YYZ
Pearson Intl.
MCO
Orlando Intl.
CA $349 Roundtrip, found 5 days ago
CA $349
Roundtrip
found 5 days ago
Select Air Canada flight, departing Wed, Nov 4 from Pearson Intl. to Orlando Intl., returning Tue, Nov 10, priced at CA $349 found 5 days ago
Wed, Jun 17 - Wed, Jun 24
YYZ
Pearson Intl.
MLB
Orlando Melbourne Intl.
CA $413 Roundtrip, found 2 days ago
CA $413
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Jun 17 from Pearson Intl. to Orlando Melbourne Intl., returning Wed, Jun 24, priced at CA $413 found 2 days ago
Thu, Jun 25 - Tue, Jun 30
YUL
Pierre Elliott Trudeau Intl.
MCO
Orlando Intl.
CA $447 Roundtrip, found 1 hour ago
CA $447
Roundtrip
found 1 hour ago
Select Delta flight, departing Thu, Jun 25 from Pierre Elliott Trudeau Intl. to Orlando Intl., returning Tue, Jun 30, priced at CA $447 found 1 hour ago
OriginDestinationTravel datesFlights from*
MSYOrlandoJuly 18 to July 22CA $229
LGAOrlandoJuly 21 to August 3CA $230
DTWOrlandoAugust 25 to September 2CA $274
JFKOrlandoJune 24 to July 3CA $291
EWROrlandoJune 9 to June 16CA $326
DTWMelbourneSeptember 1 to September 26CA $425
CLTOrlandoJuly 21 to July 25CA $463
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
JFKVero BeachMay 30 to June 15CA $326
JFKOrlandoMay 31 to June 5CA $446
LGAOrlandoMay 30 to June 4CA $465
MSYOrlandoMay 29 to June 1CA $475
EWROrlandoMay 30 to June 4CA $560
DTWOrlandoMay 30 to June 4CA $562
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Westgate Palace Hotel / Universal / I-Drive
4.0-star property

Westgate Palace Hotel / Universal / I-Drive

Jun 15 - Jun 20

5 night stay

Toronto (YYZ) to Orlando (MCO)

WestJet • Coach

Orlando (MCO) to Toronto (YYZ)

Air Canada • Coach
Price was CA $1,651, price is now CA $748 per person
CA $748
per person
found 1 day ago
Seasons Florida Resort
2.0-star property

Seasons Florida Resort

Jul 4 - Jul 11

7 night stay

Ottawa (YOW) to Orlando (MCO)

Porter Airlines • Coach

Orlando (MCO) to Ottawa (YOW)

Air Canada • Coach
Price was CA $1,307, price is now CA $807 per person
CA $807
per person
found 1 day ago
Margaritaville Cottages Orlando by Vstays with H2O Waterpark
4.0-star property

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Aug 11 - Aug 18

7 night stay

Toronto (YYZ) to Orlando (MCO)

Air Canada • Roundtrip • Coach
Price was CA $2,851, price is now CA $1,786 per person
CA $1,786
per person
found 1 day ago
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Travelers ❤️ These Osceola County 🏨

Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration

3 out of 5
2975 Arabian Nights Blvd Kissimmee FL
Book a stay at this family-friendly condo in Kissimmee. Enjoy free WiFi, 7 outdoor pools, and 7 hot tubs. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Old Town and ESPN Wide World of Sports Complex are located nearby.
8.6/10 Excellent! (4,182 reviews)
"Loved everything ❤️ Family oriented."

Reviewed on May 22, 2026

Opens in a new windowVacation Village Orlando, Celebration
Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

3 out of 5
7491 W Irlo Bronson Memorial Hwy Kissimmee FL
Stay at this resort in Kissimmee. Enjoy free breakfast, free WiFi, and 2 hot tubs. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World of Sports Complex are located nearby.
9.4/10 Exceptional! (4,126 reviews)
"Super clean. Ridiculous value! Terrific buffet breakfast included with room... Eggs, bacon AND sausage, potatos, waffles, etc. great pool areas (main pool and lazy river) with good shaded seating areas if that's your preference. If back in the area, will definitely look too stay here again. Cuban ..."

Reviewed on May 22, 2026

Opens in a new windowKompose Boutique Resort at Theme Parks
Margaritaville Resort Orlando with H2O Waterpark

Margaritaville Resort Orlando with H2O Waterpark

4 out of 5
8000 Fins Up Circle Kissimmee FL
Book a stay at this spa resort in Kissimmee. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the restaurant in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and Disney's Hollywood Studios® are located nearby.
8.8/10 Excellent! (3,597 reviews)
"This is my second time staying here and each time I couldn't wait to go back ! The place is clean and the staff is wonderful . There's a rental car in the lobby and even that gentleman was very helpful . Each time I have traveled there , there was a big event going on so it gets a big congested at ..."

Reviewed on May 23, 2026

Opens in a new windowMargaritaville Resort Orlando with H2O Waterpark
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Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
4944 W. Irlo Bronson Memorial Highway Kissimmee FL
Stay at this hotel in Kissimmee. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Old Town and Disney Springs™ are located nearby.
8.2/10 Very Good! (5,151 reviews)
"good"

Reviewed on May 22, 2026

Opens in a new windowPalazzo Lakeside Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much is the cheapest flight to Osceola County?
Within the last seven days, the cheapest roundtrip flight to Osceola County cost CA $160 on our site. Check out our excellent deals, book your tickets and look forward to your next exciting getaway. This price was available on Travelocity for flights to Osceola County departing within the next year. Prices and availability are subject to change. Additional terms apply.
What is the cheapest month to fly to Osceola County?
Leave January clear in your calendar, because it's the cheapest month to head to Osceola County. That's according to Travelocity's direct flight demand between January and December last year. With more money in your pocket, you can upgrade your hotel booking, go to a concert or whatever else you'd like to do.
How can I check my flight status to Osceola County?
Get alerts about your flight status, any gate changes and more with Trips. This convenient portal is located at the top right of our homepage and is where you can view and manage your bookings. Create your account in seconds and away you go. Or, download the Travelocity app and look up the details of your flight to Osceola County while you're on the go — and even when you're offline. The app can sort out all your booking needs. Whether you want to organize transportation to or from the airport or share itinerary details with any members of your family flying with you, our trusty app has your back.
How do I find the best deals on flights to Osceola County?
One easy way to find an amazing deal is to be flexible with your dates. Start by searching for your flight to Osceola County, then click on the "Flexible dates" box at the top of the page. This will allow you to compare prices for the surrounding days. Like more advice? Book in advance. To give you an idea of costs, CA $160 was the most affordable price for a roundtrip flight to Osceola County in the last seven days on our site. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Osceola County with Travelocity?
If you're chasing cheap flights to Osceola County, you'll uncover some top deals with Travelocity. From cheap family flights with low-cost airlines to flexible ticket options, we can help with your journey. Enjoy a hassle-free trip with our 24/7 customer support, Price Match Guarantee and free cancellations with most hotels and activities. Start packing your bags and get set to step onboard a plane to this interesting destination.
What are the most popular flight routes to Osceola County?
With great connections, booking flights to Osceola County is stress-free. Here's a selection of the main flight routes to this must-see travel destination:

  • Newark, NJ (EWR-Liberty Intl.) to Orlando Intl. Airport (MCO) - 3,839 flights a month.
  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Orlando Intl. Airport (MCO) - 3,536 flights a month.
  • Philadelphia, PA (PHL-Philadelphia Intl.) to Orlando Intl. Airport (MCO) - 2,769 flights a month.

How much is a flight to Osceola County on average?
Based on prices found on Travelocity over the last seven days, roundtrip flights to Osceola County were between CA $160 and CA $562. When you're ready to jet off, Travelocity will help you find a fare that won't blow your budget. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.