$45 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.

Sat, Apr 4 - Mon, Apr 13
BOS
Logan Intl.
MCO
Orlando Intl.
$146 Roundtrip, just found
$146
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Apr 4 from Logan Intl. to Orlando Intl., returning Mon, Apr 13, priced at $146 just found
Sun, Apr 5 - Thu, Apr 16
PSM
Portsmouth Intl.
MCO
Orlando Intl.
$179 Roundtrip, found 3 hours ago
$179
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Sun, Apr 5 from Portsmouth Intl. to Orlando Intl., returning Thu, Apr 16, priced at $179 found 3 hours ago
Sat, Apr 4 - Wed, Apr 8
PVD
T.F. Green
MCO
Orlando Intl.
$244 Roundtrip, found 1 hour ago
$244
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Sat, Apr 4 from T.F. Green to Orlando Intl., returning Wed, Apr 8, priced at $244 found 1 hour ago
Sat, Apr 4 - Wed, Apr 8
ORH
Worcester Regional
MCO
Orlando Intl.
$337 Roundtrip, found 3 days ago
$337
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Sat, Apr 4 from Worcester Regional to Orlando Intl., returning Wed, Apr 8, priced at $337 found 3 days ago

Airfares from $45 One Way, $117 Round Trip from Boston to Winter Park

Prices starting at $117 for return flights and $45 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, Jun 6 - Sat, Jun 13
PSM
Portsmouth
MCO
Orlando
$117 Roundtrip, just found
$117
Roundtrip
just found
Select Breeze Airways flight, departing Sat, Jun 6 from Portsmouth to Orlando, returning Sat, Jun 13, priced at $117 just found
Sat, May 9 - Thu, May 14
BOS
Boston
MCO
Orlando
$118 Roundtrip, found 2 hours ago
$118
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sat, May 9 from Boston to Orlando, returning Thu, May 14, priced at $118 found 2 hours ago
Sun, Apr 5 - Wed, Apr 15
BOS
Boston
MCO
Orlando
$126 Roundtrip, found 1 day ago
$126
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sun, Apr 5 from Boston to Orlando, returning Wed, Apr 15, priced at $126 found 1 day ago
Wed, Sep 2 - Wed, Sep 9
MHT
Manchester
MCO
Orlando
$135 Roundtrip, found 3 days ago
$135
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Wed, Sep 2 from Manchester to Orlando, returning Wed, Sep 9, priced at $135 found 3 days ago
Thu, Aug 27 - Wed, Sep 2
PVD
Providence
MCO
Orlando
$169 Roundtrip, found 1 day ago
$169
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Aug 27 from Providence to Orlando, returning Wed, Sep 2, priced at $169 found 1 day 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)

Apr 29 - May 2

3 night stay

Boston (BOS) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $526, price is now $309 per person
$309
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 Palace Hotel / Universal / I-Drive
4.0-star property

Westgate Palace Hotel / Universal / I-Drive

8.8/10 Excellent! (1,228 reviews)

Apr 29 - May 3

4 night stay

Boston (BOS) to Orlando (MCO)

Frontier Airlines • Coach

Orlando (MCO) to Boston (BOS)

Southwest Airlines • Coach
Save 100% on your flight
Price was $885, price is now $523 per person
$523
per person
found 1 day ago
Great location had a good time

Reviewed on Dec 28, 2025

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
3.0-star property

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

7.8/10 Good! (381 reviews)

May 2 - May 5

3 night stay

Boston (BOS) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $506, price is now $314 per person
$314
per person
found 1 day ago
The staff were amazing, the parking for the hotel was horrible.

Reviewed on Jan 3, 2026

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Winter Park first class flight packages

Price found within the past 48 hours. Click for updated prices.
Seasons Florida Resort
2.0-star property

Seasons Florida Resort

9/10 Wonderful! (3,493 reviews)

May 11 - May 18

7 night stay

Boston (BOS) to Orlando (MCO)

American Airlines • FirstClass

Orlando (MCO) to Boston (BOS)

Spirit Airlines • FirstClass
Price was $1,135, price is now $830 per person
$830
per person
found 4 hours ago
I rated 5-stars for the location and price of the stay. The rooms were in fact clean, but perhaps the age of the hotel (even though renovated) had a particular smell that only helped when running the a/c which wasn’t needed (I visited during the January attic blast).

Reviewed on Feb 10, 2026

Bryan’s Spanish Cove
3.0-star property

Bryan’s Spanish Cove

9.4/10 Exceptional! (1,013 reviews)

May 11 - May 18

7 night stay

Boston (BOS) to Orlando (MCO)

American Airlines • FirstClass

Orlando (MCO) to Boston (BOS)

Spirit Airlines • FirstClass
Price was $1,433, price is now $1,075 per person
$1,075
per person
found 4 hours ago
Clean apartment and great staff. Communication was clear and professional. Very nice to be by a lake.

Reviewed on Sep 27, 2025

Evermore Orlando Resort
4.0-star property

Evermore Orlando Resort

9.6/10 Exceptional! (587 reviews)

May 11 - May 18

7 night stay

Boston (BOS) to Orlando (MCO)

American Airlines • FirstClass

Orlando (MCO) to Boston (BOS)

Spirit Airlines • FirstClass
Save 100% on your flight
Price was $3,507, price is now $2,648 per person
$2,648
per person
found 4 hours ago
Amazing for families visting Orlando.

Reviewed on Oct 24, 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.