
$41 Cheap flight deals from Boston (BOS) to Leesburg (ORL)
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This Weekend's Flight Deals from Boston to Leesburg
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 $41 One Way, $94 Round Trip from Boston to Leesburg
Prices starting at $94 for return flights and $41 for one-way flights to Leesburg were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Leesburg economy flight packages



Margaritaville Cottages Orlando by Vstays with H2O Waterpark
Dec 7 - Dec 12
Boston (BOS) to Orlando (MCO)
Leesburg packages with premium economy flights



Meliá Orlando Celebration
Dec 30 - Jan 4
Boston (BOS) to Orlando (MCO)
Reviewed on Nov 5, 2026
More About Flying To Leesburg from Boston
Route Information for Flights from Boston to Leesburg
Origin Airport IATA Code | BOS |
|---|---|
Destination Airport IATA Code | ORL |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Boston to Leesburg
When you’re ready to take your next trip, get the most affordable prices on flights from Boston to Leesburg with Orbitz! The guaranteed low prices and cutting-edge mobile tools on Orbits make it easy for you to plan your next great vacation.
Keep Up With Sudden Flight Changes
As any traveler knows, air travel can suddenly be temporarily halted due to service disruptions. Along with offering the best fares for flights from Boston to Leesburg, Orbitz also offers free mobile phone and email alerts that help you keep up with sudden changes to your flight plans. Choose from email, text, or voice message alerts.
Get Great Prices for Boston to Leesburg Flights
Orbitz features both an Android app and an iPhone app to give you the lowest prices for Boston to Leesburg flights. Use these mobile apps to get updates on your flight, the details of your itinerary, and to learn about available hotel deals in the area.
Fly for Less and Earn Miles
Did you know you can earn miles and points for your frequent flyer program with Orbitz? To do this with specific flights from Boston to Leesburg, enter your frequent flyer account number when you book your ticket online. For even more convenience, keep a record of your loyalty travel program numbers directly with Orbitz by storing them in your account profile. This way, you can add your account numbers to your next reservation for Boston to Leesburg flights automatically without the annoying hassle of having to look them up.
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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.


