$44 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, Apr 5 - Fri, Apr 17
BOS
Logan Intl.
MCO
Orlando Intl.
$120 Roundtrip, found 3 hours ago
$120
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sun, Apr 5 from Logan Intl. to Orlando Intl., returning Fri, Apr 17, priced at $120 found 3 hours ago
Sun, Apr 5 - Thu, Apr 16
PSM
Portsmouth Intl.
MCO
Orlando Intl.
$172 Roundtrip, found 2 days ago
$172
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sun, Apr 5 from Portsmouth Intl. to Orlando Intl., returning Thu, Apr 16, priced at $172 found 2 days ago
Sat, Apr 4 - Thu, Apr 9
PVD
T.F. Green
MCO
Orlando Intl.
$299 Roundtrip, found 21 hours ago
$299
Roundtrip
found 21 hours ago
Select Breeze Airways flight, departing Sat, Apr 4 from T.F. Green to Orlando Intl., returning Thu, Apr 9, priced at $299 found 21 hours ago
Sun, Apr 5 - Thu, Apr 16
MHT
Manchester-Boston Regional
MCO
Orlando Intl.
$322 Roundtrip, just found
$322
Roundtrip
just found
Select Breeze Airways flight, departing Sun, Apr 5 from Manchester-Boston Regional to Orlando Intl., returning Thu, Apr 16, priced at $322 just found

Airfares from $44 One Way, $109 Round Trip from Boston to Winter Park

Prices starting at $109 for return flights and $44 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.

Thu, Apr 9 - Wed, Apr 15
BOS
Boston
MCO
Orlando
$109 Roundtrip, found 4 hours ago
$109
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Thu, Apr 9 from Boston to Orlando, returning Wed, Apr 15, priced at $109 found 4 hours ago
Thu, Apr 9 - Wed, Apr 15
BOS
Boston
MCO
Orlando
$109 Roundtrip, found 4 hours ago
$109
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Thu, Apr 9 from Boston to Orlando, returning Wed, Apr 15, priced at $109 found 4 hours ago
Sun, Apr 5 - Thu, Apr 16
BOS
Boston
MCO
Orlando
$110 Roundtrip, found 1 day ago
$110
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sun, Apr 5 from Boston to Orlando, returning Thu, Apr 16, priced at $110 found 1 day ago
Sun, May 24 - Sat, May 30
PSM
Portsmouth
MCO
Orlando
$111 Roundtrip, found 17 hours ago
$111
Roundtrip
found 17 hours ago
Select Breeze Airways flight, departing Sun, May 24 from Portsmouth to Orlando, returning Sat, May 30, priced at $111 found 17 hours ago
Wed, Sep 2 - Wed, Sep 9
MHT
Manchester
MCO
Orlando
$132 Roundtrip, found 3 days ago
$132
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Wed, Sep 2 from Manchester to Orlando, returning Wed, Sep 9, priced at $132 found 3 days ago

Winter Park economy flight packages

Price found within the past 48 hours. Click for updated prices.
Westgate Town Center Resort
4.0-star property

Westgate Town Center Resort

8/10 Very Good! (1,510 reviews)

May 12 - May 16

4 night stay

Boston (BOS) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $510, price is now $249 per person
$249
per person
found 1 day ago
We took our 3 year old nephew here and he had a BLAST! There is so much to do, we didn’t leave for 2 of the 3 days that we stayed. He’s about 42 inches which got him on most of the slides but not all. Keep size in mind when booking for little ones because if they’re under 40in they’re limited to the slides. He was a little bummed that he couldn’t do the pirates plunge (biggest slide) but there were enough distractions that it didn’t matter. Also, the lazy river is great! Just be careful with the big kids, they tend to knock the little ones over or into the wall because they’re just running through it. The water park is an extra fee FYI There’s “ice” skating, swan paddle boats, water park, mini golf, a train trolly, restaurants, arcade, jungle gym, multiple pools. Definitely a good spot if you don’t want to do the parks every day that you’re there! Highly recommend.

Reviewed on Apr 6, 2025

Westgate Blue Tree Resort in Lake Buena Vista
3.5-star property

Westgate Blue Tree Resort in Lake Buena Vista

8.6/10 Excellent! (1,005 reviews)

May 13 - May 19

6 night stay

Boston (BOS) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $762, price is now $407 per person
$407
per person
found 1 day ago
The place is very nice! However, the washer did not work.

Reviewed on Oct 31, 2025

Hilton Daytona Beach Oceanfront Resort
4.0-star property

Hilton Daytona Beach Oceanfront Resort

7.4/10 Good! (4,965 reviews)

May 22 - May 25

3 night stay

Boston (BOS) to Orlando (MCO)

Frontier Airlines • Non-stop • Coach

Orlando (MCO) to Boston (BOS)

Southwest Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,538, price is now $945 per person
$945
per person
found 24 hours ago
Excellent staff… excellent room… GORGEOUS views… incredible location!!! Everything was perfect!

Reviewed on Dec 4, 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.