
$44 Cheap flight deals from Boston (BOS) to Winter Garden (ORL)
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This Weekend's Flight Deals from Boston to Winter Garden
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.
Airfares from $44 One Way, $110 Round Trip from Boston to Winter Garden
Prices starting at $110 for return flights and $44 for one-way flights to Winter Garden were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Winter Garden economy flight packages

Westgate Lakes Resort & Spa Universal Studios Area
May 8 - May 11
Boston (BOS) to Orlando (MCO)
Orlando (MCO) to Boston (BOS)
Reviewed on Feb 12, 2026

Palazzo Lakeside Hotel
May 7 - May 10
Boston (BOS) to Orlando (MCO)
Orlando (MCO) to Boston (BOS)
Reviewed on Feb 9, 2026

Westgate Cocoa Beach Resort
May 1 - May 5
Boston (BOS) to Orlando (MCO)
Reviewed on Oct 5, 2025
Winter Garden packages with premium economy flights

Florida Hotel & Conference Center in the Florida Mall
May 22 - May 26
Boston (BOS) to Orlando (MCO)
Orlando (MCO) to Boston (BOS)
Reviewed on Dec 9, 2025

Margaritaville Cottages Orlando by Vstays with H2O Waterpark
May 22 - May 26
Boston (BOS) to Orlando (MCO)
Orlando (MCO) to Boston (BOS)
Reviewed on Oct 7, 2024

The Delaney Hotel
May 22 - May 26
Boston (BOS) to Orlando (MCO)
Orlando (MCO) to Boston (BOS)
Reviewed on Jul 8, 2025
Winter Garden first class flight packages

Seasons Florida Resort
May 19 - May 23
Boston (BOS) to Orlando (MCO)
Reviewed on Feb 10, 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark
May 19 - May 23
Boston (BOS) to Orlando (MCO)
Reviewed on Oct 7, 2024

Westgate Town Center Resort
May 19 - May 23
Boston (BOS) to Orlando (MCO)
Reviewed on Apr 6, 2025
More About Flying To Winter Garden from Boston
Route Information for Flights from Boston to Winter Garden
Origin Airport IATA Code | BOS |
|---|---|
Destination Airport IATA Code | ORL |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Boston to Winter Garden
Orbitz has your discount air ticket deals for flights from Boston to Winter Garden. The guaranteed low prices from flights and hotels to car rentals and vacation packages make Orbitz the perfect travel website for budget trip planning.
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Bargain Boston to Winter Garden Flights With Mobile Apps
Download the cutting-edge Orbitz app for either Android or iPhone, and use it to check on the status of your upcoming flights from Boston to Winter Garden at any time. These apps also make it easy for you to book discount hotel rates in your destination city and check for deals on future Boston to Winter Garden flights.
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Winter Garden Airports
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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.



