Cheap flights To Middleburg (JAX) from $41

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Cheap Flights to Middleburg from $41 One Way, $82 Round Trip

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Wed, Aug 26 - Wed, Sep 2
BDL
Bradley Intl.
JAX
Jacksonville Intl.
$82 Roundtrip, found 4 days ago
$82
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Wed, Aug 26 from Bradley Intl. to Jacksonville Intl., returning Wed, Sep 2, priced at $82 found 4 days ago
Wed, Aug 26 - Wed, Sep 2
BDL
Bradley Intl.
JAX
Jacksonville Intl.
$87 Roundtrip, found 4 days ago
$87
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Wed, Aug 26 from Bradley Intl. to Jacksonville Intl., returning Wed, Sep 2, priced at $87 found 4 days ago
Mon, Mar 2 - Mon, Mar 2
PHL
Philadelphia Intl.
JAX
Jacksonville Intl.
$87 Roundtrip, found 2 days ago
$87
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Mar 2 from Philadelphia Intl. to Jacksonville Intl., returning Mon, Mar 2, priced at $87 found 2 days ago
Sat, Sep 5 - Sat, Sep 12
BDL
Bradley Intl.
JAX
Jacksonville Intl.
$92 Roundtrip, found 7 hours ago
$92
Roundtrip
found 7 hours ago
Select Breeze Airways flight, departing Sat, Sep 5 from Bradley Intl. to Jacksonville Intl., returning Sat, Sep 12, priced at $92 found 7 hours ago
Mon, Feb 23 - Fri, Apr 17
PHL
Philadelphia Intl.
JAX
Jacksonville Intl.
$94 Roundtrip, found 3 days ago
$94
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, Feb 23 from Philadelphia Intl. to Jacksonville Intl., returning Fri, Apr 17, priced at $94 found 3 days ago
Sat, Mar 14 - Fri, Mar 20
PHL
Philadelphia Intl.
JAX
Jacksonville Intl.
$99 Roundtrip, found 1 day ago
$99
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Mar 14 from Philadelphia Intl. to Jacksonville Intl., returning Fri, Mar 20, priced at $99 found 1 day ago
Sat, Aug 22 - Sat, Aug 29
BDL
Bradley Intl.
JAX
Jacksonville Intl.
$102 Roundtrip, found 4 days ago
$102
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Sat, Aug 22 from Bradley Intl. to Jacksonville Intl., returning Sat, Aug 29, priced at $102 found 4 days ago
Sun, Mar 15 - Sat, Mar 21
PHL
Philadelphia Intl.
JAX
Jacksonville Intl.
$105 Roundtrip, found 2 days ago
$105
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sun, Mar 15 from Philadelphia Intl. to Jacksonville Intl., returning Sat, Mar 21, priced at $105 found 2 days ago
Mon, Mar 2 - Wed, Mar 4
BOS
Logan Intl.
JAX
Jacksonville Intl.
$148 Roundtrip, found 1 day ago
$148
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Mon, Mar 2 from Logan Intl. to Jacksonville Intl., returning Wed, Mar 4, priced at $148 found 1 day ago
Thu, Apr 16 - Thu, Apr 23
JFK
John F. Kennedy Intl.
JAX
Jacksonville Intl.
$160 Roundtrip, found 1 hour ago
$160
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Thu, Apr 16 from John F. Kennedy Intl. to Jacksonville Intl., returning Thu, Apr 23, priced at $160 found 1 hour ago

Middleburg Flight Information

Traveling To
Middleburg
Destination Airport IATA Code
JAX
Number of Airlines Serving
Airlines
Breeze Airways, Frontier Airlines, JetBlue Airways
Flight Price
$82
Earliest Departing Flight
Latest Departing Flight

Book Your Flight & Hotel Together & Save

Middleburg economy flight packages

Price found within the past 48 hours. Click for updated prices.
Southbank Apartments by Landing
4.0-star property

Southbank Apartments by Landing

Mar 28 - Apr 4

7 night stay

Boston (BOS) to Jacksonville (JAX)

Delta • Roundtrip • Coach
Price was $871, price is now $647 per person
$647
per person
found 1 day ago
Amelia by the South
4.0-star property

Amelia by the South

Apr 1 - Apr 5

4 night stay

Boston (BOS) to Jacksonville (JAX)

Frontier Airlines • Non-stop • Coach

Jacksonville (JAX) to Boston (BOS)

Delta • Non-stop • Coach
Save 100% on your flight
Price was $5,500, price is now $3,851 per person
$3,851
per person
found 18 hours ago
Amelia by the Sea
4.0-star property

Amelia by the Sea

Apr 1 - Apr 5

4 night stay

Boston (BOS) to Jacksonville (JAX)

Frontier Airlines • Non-stop • Coach

Jacksonville (JAX) to Boston (BOS)

Delta • Non-stop • Coach
Save 100% on your flight
Price was $5,527, price is now $3,878 per person
$3,878
per person
found 18 hours ago
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Middleburg premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Southbank Hotel by Marriott Jacksonville Riverwalk
3.5-star property

Southbank Hotel by Marriott Jacksonville Riverwalk

8.2/10 Very Good! (1,597 reviews)

Apr 6 - Apr 10

4 night stay

Minneapolis (MSP) to Jacksonville (JAX)

Delta • Roundtrip • PremiumEconomy
Price was $1,019, price is now $827 per person
$827
per person
found 5 hours ago
The staff was great and check in was easy. Rooms were nice and clean. The shared areas were nice as well. The area around the hotel was amazing, definitely go on the Riverwalk. I would stay here again

Reviewed on Jan 13, 2026

Hyatt Regency Jacksonville
4.0-star property

Hyatt Regency Jacksonville

9/10 Wonderful! (1,352 reviews)

Apr 6 - Apr 10

4 night stay

Minneapolis (MSP) to Jacksonville (JAX)

Delta • Roundtrip • PremiumEconomy
Price was $1,175, price is now $925 per person
$925
per person
found 5 hours ago
Great staff , location.

Reviewed on Jan 2, 2026

Beachside Motel
2.0-star property

Beachside Motel

9.2/10 Wonderful! (1,000 reviews)

Apr 6 - Apr 10

4 night stay

Minneapolis (MSP) to Jacksonville (JAX)

Delta • Roundtrip • PremiumEconomy
Price was $1,082, price is now $877 per person
$877
per person
found 5 hours ago
Room was very clean, staff was super friendly.

Reviewed on Jan 17, 2026

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Middleburg first class flight packages

Price found within the past 48 hours. Click for updated prices.
Hyatt Regency Jacksonville
4.0-star property

Hyatt Regency Jacksonville

9/10 Wonderful! (1,352 reviews)

Mar 17 - Mar 20

3 night stay

Boston (BOS) to Jacksonville (JAX)

Delta • Non-stop roundtrip • FirstClass
Price was $986, price is now $846 per person
$846
per person
found 7 hours ago
Great staff , location.

Reviewed on Jan 2, 2026

Hampton Inn Jacksonville Beach/Oceanfront
3.0-star property

Hampton Inn Jacksonville Beach/Oceanfront

9.2/10 Wonderful! (2,552 reviews)

Mar 17 - Mar 20

3 night stay

Boston (BOS) to Jacksonville (JAX)

Delta • Non-stop roundtrip • FirstClass
Price was $1,016, price is now $883 per person
$883
per person
found 7 hours ago
Very nice folks. Clean. Great breakfast.

Reviewed on Jan 7, 2026

Marriott Jacksonville Downtown
4.0-star property

Marriott Jacksonville Downtown

8.4/10 Very Good! (1,002 reviews)

Mar 17 - Mar 20

3 night stay

Boston (BOS) to Jacksonville (JAX)

Delta • Non-stop roundtrip • FirstClass
Price was $957, price is now $848 per person
$848
per person
found 7 hours ago
Floor in room nor shower was clean. No ventilation in bathroom. Long wait for valet parking and only option for parking available.

Reviewed on May 28, 2025

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Middleburg

Why search for low cost fares on your flights to Middleburg when Orbitz offers the guaranteed lowest prices on foreign and domestic flights? When you travel with Orbitz you can benefit from:

Bargain Flights to Middleburg

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Frequent Flyer Program Enrolment

Orbitz finds you the lowest fares, but you can still add your miles to your frequent flyer program to earn miles or points on selected flights to Middleburg. When making your booking, reference your frequent flyer number to receive discounts in the future.

Outstanding Customer Service

Orbitz values your business and wants to ensure that all of your flights are as easy as possible to book. If you have booked a flight to Middleburg but need to cancel it, you may be able to do so online. If you have any questions or need help, the dedicated Orbitz customer service team is always standing by.

Frequently asked questions

Which airlines fly to Middleburg?
With 20 airlines flying into Jacksonville Intl. Airport (JAX), you'll be exploring this exciting destination before you know it. Ticket costs depend on where you're coming from and when you plan to travel. You'll no doubt snap up a cheap deal to Middleburg from one of these well-known domestic carriers:

  • American Airlines - 287 flights to Middleburg per month
  • Delta - 259 flights to Middleburg per month
  • United Airlines - 235 flights to Middleburg per month

What is the best airport to fly to in Middleburg?
Jacksonville Intl. Airport (JAX) is the city's only airport, so your only tough decision will be the aisle seat or the window seat. Central Middleburg is around 30 miles away and where many travelers start their adventure.
How much is a flight to Middleburg?
This week, prices ranged between $82 and $160 for a return trip to Middleburg. One-way tickets from Hartford (BDL) dropped down to $41 during the same time period.
How to book the cheapest flight to Middleburg?
With some of the most affordable flight deals around, you can jet for less with Orbitz. The following pointers will help you snap up cheap flights to Middleburg — and leave you with extra cash in your wallet:

  • Depending on where you're departing from, select the 'Nearby airports' function (located under the departure and arrival options). At times, other departure points offer better value for money.
  • Similarly, click on the 'Show flexible dates' link to bring up the airfares on days around your chosen departure. It's possible to pick up cheaper flight deals if your travel dates are flexible.
  • Select 'Show options' to fine tune your search results. You can pick your preferred airline and seating class here. Under 'Sort & Filter' to the left, you can even specify whether you want to fly in the morning, afternoon or evening.
  • The early bird gets the biggest savings, so book as soon as you've worked out your travel dates. The cheapest fares get snapped up fast and prices rise as the departure date nears.
  • Combine your flights, hotels and car rentals into a competitive package deal. Save your dollars for things you're really excited about, like exploring every corner of Middleburg.
  • If practical, don't travel in the most popular seasons. Airfares are usually at their most expensive during summer, school breaks and around other vacation times like Easter, Thanksgiving and Christmas.

How long is a flight to Middleburg?
The destination you're leaving from and if you have a stopover help determine your flight time. However, these three busy routes to Middleburg will offer some insight:

  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Jacksonville Intl. Airport (JAX) - 1 hour and 10 minutes
  • New York, NY (JFK-John F. Kennedy Intl.) to Jacksonville Intl. Airport (JAX) - 2 hours and 34 minutes
  • New York, NY (LGA-LaGuardia) to Jacksonville Intl. Airport (JAX) - 2 hours and 30 minutes

What is the best time to book a flight to Middleburg?
If you can, purchase your seats to Middleburg in January. This is the best month for low airfares, closely followed by February and August. With a little organizing, you're sure to find a cheap flight with Orbitz.
What day of the week is the cheapest to book a flight to Middleburg?
Make a booking on a Tuesday, Wednesday or Saturday. Generally, these are the cheapest days to purchase airfares to Middleburg. The vacation of your dreams starts with a terrific flight deal!
What is the cheapest day of the week to fly to Middleburg?
Look into leaving early in the week to get cheap flights to Middleburg. Orbitz data from 2020 suggests Monday is typically the cheapest day to hop on a plane, followed by Tuesday. Saturdays were shown to have the most expensive airfares. This is probably because most passengers prefer to start their trip at the end of the week.
What is the cheapest month to fly to Middleburg?
To pick up cheap flights to Middleburg, you should pack your suitcase and jet off in August. Orbitz data shows that generally, this is the best month to save a bundle on your airfare. If you're hoping to jet to Middleburg in June, be aware that this is the least affordable time of year to travel.
Which airlines allow free cancellation?
When you search for flights on Orbitz, click on "Filter by flexible change policies." This filter will quickly find all the carriers offering free cancellation and no change fees. Breathe easy knowing that if things change, your ticket can too.
What do I need for the flight to Middleburg?
The key to a comfortable flight is being well prepared. Listed below are some tips that'll help get you ready for your journey:

  • Whether you print it out at home or use an electronic one, you'll need your boarding pass to walk on to the plane. You'll also need some form of government-issued photo ID. If you're flying internationally, make sure your passport is valid and you've looked into visa requirements.
  • To keep you entertained on the short hop to Middleburg, download some new tracks or stock up the audiobook library on your phone. Food can also be a tasty distraction while in the air, so pack some snacks.
  • Even if you're traveling when it's 100 degrees outside, carry a warm top or scarf on board with you. Airplane cabins can get quite chilly!

How many direct flights are there to Middleburg?
There are 200 flights that travel direct to Middleburg every month, so you won't have to worry about any long stopovers. Reserve a fare with American Airlines or Delta Air Lines and then kick back, relax and enjoy the journey. United Airlines, Southwest Airlines, JetBlue Airways and Frontier Airlines also offer nonstop flights to Middleburg.
How do I get cheap first-class/business deals to Middleburg?
Experienced travelers have mastered the art of finding first or business-class flights to Middleburg without the hefty price tag. Follow their lead with these helpful hints:

  • Flexibility is essential. By being open to various travel dates, you'll have more chances of picking up a deal on your airfares.
  • A lot of budget airlines these days have excellent business-class seating without the hefty fees.
  • Bid for an upgrade in online auctions or upgrade your fare with loyalty points.

How to get into Middleburg from the airport?
Jump in a Jacksonville Intl. Airport (JAX) car rental from JAX airport and easily make your way to downtown Middleburg. Choose a vehicle from one of the popular rental outlets on-site such as Dollar, Payless or Budget. After you've packed your baggage in the trunk, the center of the city is 30 miles to the southwest. If you'd prefer to take a taxi into town and zoom off in your own set of wheels from there instead, browse through our Middleburg car rentals.
What is the best time to go to Middleburg?
If you'd like to immerse yourself in the culture of Middleburg in the peak season, June, July and September are the top months to visit. June 20 marks the start of summertime in the Northern Hemisphere and is an awesome time to go if you're hooked on the great outdoors. During this time of year, average daily temperatures range from 75 ºF to 95 ºF.

More to Explore

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.