$51 Cheap flight deals from Boston (BOS) to Winter Park (ORL)

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This Weekend's Flight Deals from Boston to Winter Park

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, May 24 - Thu, May 28
PSM
Portsmouth Intl.
MCO
Orlando Intl.
$128 Roundtrip, found 2 hours ago
$128
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Sun, May 24 from Portsmouth Intl. to Orlando Intl., returning Thu, May 28, priced at $128 found 2 hours ago
Sun, May 24 - Thu, May 28
PSM
Portsmouth Intl.
MCO
Orlando Intl.
$128 Roundtrip, found 2 hours ago
$128
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Sun, May 24 from Portsmouth Intl. to Orlando Intl., returning Thu, May 28, priced at $128 found 2 hours ago
Sun, May 24 - Sat, May 30
MHT
Manchester-Boston Regional
MCO
Orlando Intl.
$218 Roundtrip, found 22 hours ago
$218
Roundtrip
found 22 hours ago
Select Breeze Airways flight, departing Sun, May 24 from Manchester-Boston Regional to Orlando Intl., returning Sat, May 30, priced at $218 found 22 hours ago
Sun, May 24 - Sun, Jun 21
PVD
T.F. Green
MCO
Orlando Intl.
$264 Roundtrip, found 16 hours ago
$264
Roundtrip
found 16 hours ago
Select Breeze Airways flight, departing Sun, May 24 from T.F. Green to Orlando Intl., returning Sun, Jun 21, priced at $264 found 16 hours ago

Airfares from $51 One Way, $102 Round Trip from Boston to Winter Park

Prices starting at $102 for return flights and $51 for one-way flights to Winter Park were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Jan 23 - Sat, Jan 30
PSM
Portsmouth
MCO
Orlando
$102 Roundtrip, found 16 hours ago
$102
Roundtrip
found 16 hours ago
Select Breeze Airways flight, departing Sat, Jan 23 from Portsmouth to Orlando, returning Sat, Jan 30, priced at $102 found 16 hours ago
Sat, Jul 25 - Wed, Jul 29
BOS
Boston
MCO
Orlando
$158 Roundtrip, found 15 hours ago
$158
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Sat, Jul 25 from Boston to Orlando, returning Wed, Jul 29, priced at $158 found 15 hours ago
Sat, Jan 23 - Sat, Jan 30
MHT
Manchester
MCO
Orlando
$160 Roundtrip, found 18 hours ago
$160
Roundtrip
found 18 hours ago
Select Breeze Airways flight, departing Sat, Jan 23 from Manchester to Orlando, returning Sat, Jan 30, priced at $160 found 18 hours ago
Mon, Sep 28 - Wed, Oct 7
PVD
Providence
MCO
Orlando
$183 Roundtrip, found 2 days ago
$183
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Mon, Sep 28 from Providence to Orlando, returning Wed, Oct 7, priced at $183 found 2 days ago
Tue, Jun 16 - Sat, Jun 20
BOS
Boston
MCO
Orlando
$222 Roundtrip, found 11 hours ago
$222
Roundtrip
found 11 hours ago
Select Delta flight, departing Tue, Jun 16 from Boston to Orlando, returning Sat, Jun 20, priced at $222 found 11 hours ago

Winter Park economy flight packages

Price found within the past 48 hours. Click for updated prices.
Westgate Lakes Resort & Spa Universal Studios Area
4.0-star property

Westgate Lakes Resort & Spa Universal Studios Area

8.4/10 Very Good! (6,417 reviews)

Jun 25 - Jun 29

4 night stay

Boston (BOS) to Orlando (MCO)

Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $977, price is now $610 per person
$610
per person
found 1 day ago
Great location to everything as far as food, Walmart, attractions etc. Beds were horrible and the parking at night. The water park only has 2 water slides and a small wave pool. It's a joke to charge guest to come in.

Reviewed on Apr 5, 2026

Westgate Palace Hotel / Universal / I-Drive
4.0-star property

Westgate Palace Hotel / Universal / I-Drive

8.8/10 Excellent! (1,254 reviews)

Jun 25 - Jun 29

4 night stay

Boston (BOS) to Orlando (MCO)

Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,226, price is now $690 per person
$690
per person
found 1 day ago
The property is nice and convenient. I took a star off because my whole party agreed that the beds were not comfortable. I don’t remember a worse mattress. Other than that, great place that was clean and spacious. Great shower pressure.

Reviewed on Apr 3, 2026

Florida Hotel & Conference Center in the Florida Mall
3.5-star property

Florida Hotel & Conference Center in the Florida Mall

9.2/10 Wonderful! (1,353 reviews)

Jun 14 - Jun 19

5 night stay

Boston (BOS) to Orlando (MCO)

Delta • Non-stop • Coach

Orlando (MCO) to Boston (BOS)

Frontier Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,125, price is now $682 per person
$682
per person
found 1 day ago
What a stunning and beautiful hotel. My son loved it also and having full access to the mall was a bonus!! Will definitely be back soon!

Reviewed on Dec 9, 2025

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More About Flying To Winter Park from Boston

Route Information for Flights from Boston to Winter Park

Origin Airport IATA Code
BOS
Destination Airport IATA Code
ORL
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Boston to Winter Park

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.