Search Cheap Flights to
Middleburg

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Middleburg Flights as Low as $155

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

United
Wed, Oct 8 - Mon, Oct 13
ORD
O'Hare Intl.
JAX
Jacksonville Intl.
$155 Roundtrip, found 10 hours ago
$155
Roundtrip
found 10 hours ago
Select United flight, departing Wed, Oct 8 from O'Hare Intl. to Jacksonville Intl., returning Mon, Oct 13, priced at $155 found 10 hours ago
American Airlines
Wed, Oct 8 - Mon, Oct 13
ORD
O'Hare Intl.
JAX
Jacksonville Intl.
$158 Roundtrip, found 10 hours ago
$158
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Wed, Oct 8 from O'Hare Intl. to Jacksonville Intl., returning Mon, Oct 13, priced at $158 found 10 hours ago
United
Fri, May 30 - Wed, Jun 4
ORD
O'Hare Intl.
JAX
Jacksonville Intl.
$158 Roundtrip, found 13 hours ago
$158
Roundtrip
found 13 hours ago
Select United flight, departing Fri, May 30 from O'Hare Intl. to Jacksonville Intl., returning Wed, Jun 4, priced at $158 found 13 hours ago
JetBlue Airways
Sat, May 31 - Wed, Jun 4
JFK
John F. Kennedy Intl.
JAX
Jacksonville Intl.
$160 Roundtrip, found 2 days ago
$160
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Sat, May 31 from John F. Kennedy Intl. to Jacksonville Intl., returning Wed, Jun 4, priced at $160 found 2 days ago
United
Tue, Jun 10 - Mon, Jun 16
EWR
Newark Liberty Intl. Airport
JAX
Jacksonville Intl.
$160 Roundtrip, found 5 days ago
$160
Roundtrip
found 5 days ago
Select United flight, departing Tue, Jun 10 from Newark Liberty Intl. Airport to Jacksonville Intl., returning Mon, Jun 16, priced at $160 found 5 days ago
Delta
Tue, May 27 - Tue, Jun 3
JFK
John F. Kennedy Intl.
JAX
Jacksonville Intl.
$160 Roundtrip, found 2 days ago
$160
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, May 27 from John F. Kennedy Intl. to Jacksonville Intl., returning Tue, Jun 3, priced at $160 found 2 days ago
United
Fri, May 30 - Wed, Jun 4
ORD
O'Hare Intl.
JAX
Jacksonville Intl.
$164 Roundtrip, found 13 hours ago
$164
Roundtrip
found 13 hours ago
Select United flight, departing Fri, May 30 from O'Hare Intl. to Jacksonville Intl., returning Wed, Jun 4, priced at $164 found 13 hours ago
United
Fri, May 30 - Wed, Jun 4
ORD
O'Hare Intl.
JAX
Jacksonville Intl.
$168 Roundtrip, found 13 hours ago
$168
Roundtrip
found 13 hours ago
Select United flight, departing Fri, May 30 from O'Hare Intl. to Jacksonville Intl., returning Wed, Jun 4, priced at $168 found 13 hours ago
United
Tue, Jun 10 - Mon, Jun 16
EWR
Newark Liberty Intl. Airport
JAX
Jacksonville Intl.
$170 Roundtrip, found 5 days ago
$170
Roundtrip
found 5 days ago
Select United flight, departing Tue, Jun 10 from Newark Liberty Intl. Airport to Jacksonville Intl., returning Mon, Jun 16, priced at $170 found 5 days ago
United
Sat, May 24 - Sun, May 25
EWR
Newark Liberty Intl. Airport
JAX
Jacksonville Intl.
$170 Roundtrip, found 1 day ago
$170
Roundtrip
found 1 day ago
Select United flight, departing Sat, May 24 from Newark Liberty Intl. Airport to Jacksonville Intl., returning Sun, May 25, priced at $170 found 1 day ago
American Airlines
Thu, Jul 3 - Sun, Jul 20
ORD
O'Hare Intl.
JAX
Jacksonville Intl.
$175 Roundtrip, found 2 days ago
$175
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Jul 3 from O'Hare Intl. to Jacksonville Intl., returning Sun, Jul 20, priced at $175 found 2 days ago
Delta
Tue, Aug 5 - Mon, Aug 11
EWR
Newark Liberty Intl. Airport
JAX
Jacksonville Intl.
$177 Roundtrip, found 4 days ago
$177
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Aug 5 from Newark Liberty Intl. Airport to Jacksonville Intl., returning Mon, Aug 11, priced at $177 found 4 days ago
United
Fri, Jun 6 - Mon, Jun 9
ORD
O'Hare Intl.
JAX
Jacksonville Intl.
$178 Roundtrip, found 20 hours ago
$178
Roundtrip
found 20 hours ago
Select United flight, departing Fri, Jun 6 from O'Hare Intl. to Jacksonville Intl., returning Mon, Jun 9, priced at $178 found 20 hours ago
American Airlines
Fri, Jun 6 - Mon, Jun 9
ORD
O'Hare Intl.
JAX
Jacksonville Intl.
$178 Roundtrip, found 20 hours ago
$178
Roundtrip
found 20 hours ago
Select American Airlines flight, departing Fri, Jun 6 from O'Hare Intl. to Jacksonville Intl., returning Mon, Jun 9, priced at $178 found 20 hours ago
Delta
Tue, May 20 - Thu, May 29
LGA
LaGuardia
JAX
Jacksonville Intl.
$207 Roundtrip, found 2 days ago
$207
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, May 20 from LaGuardia to Jacksonville Intl., returning Thu, May 29, priced at $207 found 2 days ago
Frontier Airlines
Mon, May 26 - Fri, May 30
ORD
O'Hare Intl.
JAX
Jacksonville Intl.
$337 Roundtrip, found 10 hours ago
$337
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Mon, May 26 from O'Hare Intl. to Jacksonville Intl., returning Fri, May 30, priced at $337 found 10 hours ago

Cheap Flights to Middleburg

Fall in love at first flight with your vacation to Middleburg by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Middleburg on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Middleburg, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Middleburg

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Middleburg with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the JAX airport.

What is the cheapest month to fly to Middleburg?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Middleburg are in October, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Middleburg?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Middleburg.

What airport is best to fly into Middleburg?

When you’re planning your trip to Middleburg, convenience is the name of the game. Luckily, Middleburg Jacksonville Executive at Craig Airport is nearby so you can deplane and get going on checking off everything on your Middleburg must-do list.

How much are flights to Middleburg?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Middleburg on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $155, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Middleburg?

The trick to saving a stack of cash on your flight to Middleburg? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $155 right now, why wait?

Last Minute Hotel Deals in Middleburg

Southbank Hotel by Marriott Jacksonville Riverwalk
Southbank Hotel by Marriott Jacksonville Riverwalk
3.5 out of 5
1515 Prudential Dr, Jacksonville, FL
The price is $122 per night from Jun 8 to Jun 9
$122
includes taxes & fees
Jun 8 - Jun 9
Book a stay at this business-friendly hotel in Jacksonville. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and ...
8.2/10 Very Good! (1,405 reviews)
"Overall things were good. The WiFi was a propblem. That being said a maintenance man came to our room to help us with one device."

Reviewed on May 8, 2025

Southbank Hotel by Marriott Jacksonville Riverwalk
Wyndham Garden Jacksonville
Wyndham Garden Jacksonville
3 out of 5
4660 Salisbury Road, I-95 Exit 344 (Butler Boulevard), Jacksonville, FL
The price is $81 per night from May 18 to May 19
$81
includes taxes & fees
May 18 - May 19
Book a stay at this business-friendly hotel in Jacksonville. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the ...
7.4/10 Good! (1,607 reviews)
"Staff were awesome! Rooms were very clean! Attached restaurant had great food and service!"

Reviewed on May 3, 2025

Wyndham Garden Jacksonville
Hyatt Regency Jacksonville
Hyatt Regency Jacksonville
4 out of 5
225 E Coastline Dr, Jacksonville, FL
The price is $196 per night from May 30 to May 31
$196
includes taxes & fees
May 30 - May 31
Stay at this 4-star eco-certified hotel in Jacksonville. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.8/10 Excellent! (1,225 reviews)
"Great hotel with amazing staff!!"

Reviewed on May 4, 2025

Hyatt Regency Jacksonville
Embassy Suites by Hilton Jacksonville Baymeadows
Embassy Suites by Hilton Jacksonville Baymeadows
3.5 out of 5
9300 Baymeadows Road, Jacksonville, FL
The price is $141 per night from Jun 1 to Jun 2
$141
includes taxes & fees
Jun 1 - Jun 2
Book a stay at this business-friendly hotel in Jacksonville. Enjoy free breakfast, free parking, and room service. Our guests praise the breakfast and the helpful ...
8.2/10 Very Good! (1,006 reviews)
"Only compliant is that we weren't able to get SEC network in room or Bar area. Required us to leave and not dine at restaurant in hotel and eat/drink elsewhere."

Reviewed on May 7, 2025

Embassy Suites by Hilton Jacksonville Baymeadows
Apm Inn and Suite
Apm Inn and Suite
2 out of 5
510 Lane Ave S, Jacksonville, FL
The price is $74 per night from May 10 to May 11
$74
includes taxes & fees
May 10 - May 11
Stay at this hotel in Jacksonville. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
6.6/10 (735 reviews)
"Great"

Reviewed on May 8, 2025

Apm Inn and Suite
Comfort Suites Baymeadows Near Butler Blvd
Comfort Suites Baymeadows Near Butler Blvd
3 out of 5
8277 Western Way Cir, Jacksonville, FL
The price is $113 per night from May 18 to May 19
$113
includes taxes & fees
May 18 - May 19
Stay at this 3-star business-friendly hotel in Jacksonville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
7.8/10 Good! (1,002 reviews)
"Great customer service"

Reviewed on May 4, 2025

Comfort Suites Baymeadows Near Butler Blvd
DoubleTree by Hilton Hotel Jacksonville Riverfront
DoubleTree by Hilton Hotel Jacksonville Riverfront
4 out of 5
1201 Riverplace Boulevard, Jacksonville, FL
The price is $130 per night from Jun 8 to Jun 9
$130
includes taxes & fees
Jun 8 - Jun 9
Stay at this 4-star hotel in Jacksonville. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the pool and the helpful staff in our reviews. ...
6.6/10 (1,284 reviews)
"The hotel & the personnel were very nice. But they can improve their rooms with a little maintenance."

Reviewed on May 4, 2025

DoubleTree by Hilton Hotel Jacksonville Riverfront
World Golf Village Renaissance St. Augustine Resort
World Golf Village Renaissance St. Augustine Resort
4 out of 5
500 S Legacy Trail, St. Augustine, FL
The price is $127 per night from Jun 8 to Jun 9
$127
includes taxes & fees
Jun 8 - Jun 9
Stay at this 4-star golf resort in St. Augustine. Enjoy a golf course, breakfast (surcharge), and room service. Our guests praise the helpful staff and the property ...
8.4/10 Very Good! (1,001 reviews)
"Room was noisy, balcony view and noise of what I think were large AC units. Room was also across from the very loud ice machine. Hotel was decent, not spectacular but decent."

Reviewed on May 4, 2025

World Golf Village Renaissance St. Augustine Resort
See all 1,671 properties in Middleburg
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.