Search Cheap Flights to
Jacksonville

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Jacksonville Flights as Low as $434

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

JetBlue Airways
Thu, Oct 2 - Sun, Oct 5
ORD
O'Hare Intl.
RUT
Rutland Southern Vermont Regional
$434 Roundtrip, just found
$434
Roundtrip
just found
Select JetBlue Airways flight, departing Thu, Oct 2 from O'Hare Intl. to Rutland Southern Vermont Regional, returning Sun, Oct 5, priced at $434 just found
JetBlue Airways
Thu, Oct 2 - Sun, Oct 5
ORD
O'Hare Intl.
RUT
Rutland Southern Vermont Regional
$439 Roundtrip, just found
$439
Roundtrip
just found
Select JetBlue Airways flight, departing Thu, Oct 2 from O'Hare Intl. to Rutland Southern Vermont Regional, returning Sun, Oct 5, priced at $439 just found
Delta
Thu, Oct 2 - Sun, Oct 5
ORD
O'Hare Intl.
RUT
Rutland Southern Vermont Regional
$451 Roundtrip, just found
$451
Roundtrip
just found
Select Delta flight, departing Thu, Oct 2 from O'Hare Intl. to Rutland Southern Vermont Regional, returning Sun, Oct 5, priced at $451 just found
United
Thu, Oct 2 - Sun, Oct 5
ORD
O'Hare Intl.
RUT
Rutland Southern Vermont Regional
$455 Roundtrip, just found
$455
Roundtrip
just found
Select United flight, departing Thu, Oct 2 from O'Hare Intl. to Rutland Southern Vermont Regional, returning Sun, Oct 5, priced at $455 just found
JetBlue Airways
Thu, Oct 2 - Sun, Oct 5
ORD
O'Hare Intl.
RUT
Rutland Southern Vermont Regional
$458 Roundtrip, just found
$458
Roundtrip
just found
Select JetBlue Airways flight, departing Thu, Oct 2 from O'Hare Intl. to Rutland Southern Vermont Regional, returning Sun, Oct 5, priced at $458 just found
JetBlue Airways
Thu, Oct 2 - Sun, Oct 5
ORD
O'Hare Intl.
RUT
Rutland Southern Vermont Regional
$463 Roundtrip, just found
$463
Roundtrip
just found
Select JetBlue Airways flight, departing Thu, Oct 2 from O'Hare Intl. to Rutland Southern Vermont Regional, returning Sun, Oct 5, priced at $463 just found
American Airlines
Thu, Oct 2 - Sun, Oct 5
ORD
O'Hare Intl.
RUT
Rutland Southern Vermont Regional
$479 Roundtrip, just found
$479
Roundtrip
just found
Select American Airlines flight, departing Thu, Oct 2 from O'Hare Intl. to Rutland Southern Vermont Regional, returning Sun, Oct 5, priced at $479 just found
American Airlines
Thu, Oct 2 - Sun, Oct 5
ORD
O'Hare Intl.
RUT
Rutland Southern Vermont Regional
$479 Roundtrip, just found
$479
Roundtrip
just found
Select American Airlines flight, departing Thu, Oct 2 from O'Hare Intl. to Rutland Southern Vermont Regional, returning Sun, Oct 5, priced at $479 just found
American Airlines
Thu, Oct 2 - Sun, Oct 5
ORD
O'Hare Intl.
RUT
Rutland Southern Vermont Regional
$484 Roundtrip, just found
$484
Roundtrip
just found
Select American Airlines flight, departing Thu, Oct 2 from O'Hare Intl. to Rutland Southern Vermont Regional, returning Sun, Oct 5, priced at $484 just found
United
Thu, Oct 2 - Sun, Oct 5
ORD
O'Hare Intl.
RUT
Rutland Southern Vermont Regional
$523 Roundtrip, just found
$523
Roundtrip
just found
Select United flight, departing Thu, Oct 2 from O'Hare Intl. to Rutland Southern Vermont Regional, returning Sun, Oct 5, priced at $523 just found
JetBlue Airways
Thu, Oct 2 - Sun, Oct 5
ORD
O'Hare Intl.
RUT
Rutland Southern Vermont Regional
$535 Roundtrip, just found
$535
Roundtrip
just found
Select JetBlue Airways flight, departing Thu, Oct 2 from O'Hare Intl. to Rutland Southern Vermont Regional, returning Sun, Oct 5, priced at $535 just found
Delta
Thu, Oct 2 - Sun, Oct 5
ORD
O'Hare Intl.
RUT
Rutland Southern Vermont Regional
$535 Roundtrip, just found
$535
Roundtrip
just found
Select Delta flight, departing Thu, Oct 2 from O'Hare Intl. to Rutland Southern Vermont Regional, returning Sun, Oct 5, priced at $535 just found
JetBlue Airways
Thu, Oct 2 - Sun, Oct 5
ORD
O'Hare Intl.
RUT
Rutland Southern Vermont Regional
$545 Roundtrip, just found
$545
Roundtrip
just found
Select JetBlue Airways flight, departing Thu, Oct 2 from O'Hare Intl. to Rutland Southern Vermont Regional, returning Sun, Oct 5, priced at $545 just found
Delta
Thu, Oct 2 - Sun, Oct 5
ORD
O'Hare Intl.
RUT
Rutland Southern Vermont Regional
$545 Roundtrip, just found
$545
Roundtrip
just found
Select Delta flight, departing Thu, Oct 2 from O'Hare Intl. to Rutland Southern Vermont Regional, returning Sun, Oct 5, priced at $545 just found
JetBlue Airways
Thu, Oct 2 - Sun, Oct 5
ORD
O'Hare Intl.
RUT
Rutland Southern Vermont Regional
$550 Roundtrip, just found
$550
Roundtrip
just found
Select JetBlue Airways flight, departing Thu, Oct 2 from O'Hare Intl. to Rutland Southern Vermont Regional, returning Sun, Oct 5, priced at $550 just found
American Airlines
Thu, Oct 2 - Sun, Oct 5
ORD
O'Hare Intl.
RUT
Rutland Southern Vermont Regional
$560 Roundtrip, just found
$560
Roundtrip
just found
Select American Airlines flight, departing Thu, Oct 2 from O'Hare Intl. to Rutland Southern Vermont Regional, returning Sun, Oct 5, priced at $560 just found

Cheap Flights to Jacksonville

Fall in love at first flight with your vacation to Jacksonville 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 Jacksonville on Hotwire, and you’ll be up, up, and on a getaway in no time.

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

Frequently Asked Questions About flights to Jacksonville

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Jacksonville 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 EEN airport.

What is the cheapest month to fly to Jacksonville?

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 Jacksonville are in October, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Jacksonville?

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 Jacksonville.

What airport is best to fly into Jacksonville?

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

How much are flights to Jacksonville?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Jacksonville on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $434, 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 Jacksonville?

The trick to saving a stack of cash on your flight to Jacksonville? 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 $434 right now, why wait?

Jacksonville Flight Information
Destination airport
Rutland Southern Vermont Regional
Destination airport IATA code
RUT
Roundtrip price
$433

Last Minute Hotel Deals in Jacksonville

Hotel Downstreet
Hotel Downstreet
3 out of 5
40 Main St, North Adams, MA
The price is $144 per night from Jan 7 to Jan 8
$144
includes taxes & fees
Jan 7 - Jan 8
Stay at this 3-star hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (1,005 reviews)
"Excellent"

Reviewed on Jan 4, 2025

Hotel Downstreet
Mountaineer Inn
Mountaineer Inn
2 out of 5
270 Handle Rd, West Dover, VT
The price is $174 per night from Jan 8 to Jan 9
$174
includes taxes & fees
Jan 8 - Jan 9
Stay at this motel in West Dover. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
9/10 Wonderful! (363 reviews)
"No one to greet you when you arrive or If you have questions or need something. The text was quickly answered but still like someone on property"

Reviewed on Jan 1, 2025

Mountaineer Inn
Colonial Motel And Spa
Colonial Motel And Spa
3 out of 5
889 Putney Rd, Brattleboro, VT
The price is $108 per night from Jan 8 to Jan 9
$108
includes taxes & fees
Jan 8 - Jan 9
Stay at this 3-star spa motel in Brattleboro. Enjoy free WiFi, free parking, and 2 indoor pools. Our guests praise the helpful staff and the clean rooms in our ...
6.6/10 (1,001 reviews)
"Like size of room"

Reviewed on Dec 8, 2024

Colonial Motel And Spa
Hampton Inn Brattleboro
Hampton Inn Brattleboro
2.5 out of 5
1378 Putney Road, Brattleboro, VT
The price is $102 per night from Jan 12 to Jan 13
$102
includes taxes & fees
Jan 12 - Jan 13
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the ...
8.2/10 Very Good! (1,003 reviews)
"The hotel was clean and staff were helpful. The breakfast was better than average and they have 24 hours hot coffee and tea. The pool and hot tub were closed which was a disappointment. A pipe burst in our bathroom in the middle of the night, but the staff were quick to get us a new room and were ..."

Reviewed on Jan 4, 2025

Hampton Inn Brattleboro
Mount Snow Grand Summit Resort
Mount Snow Grand Summit Resort
3 out of 5
89 Grand Summit Way, West Dover, VT
The price is $335 per night from Jan 22 to Jan 23
$335
includes taxes & fees
Jan 22 - Jan 23
Stay at this 3-star spa resort in West Dover. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Mount Snow and Ego Alley Ski Lift are ...
8.8/10 Excellent! (172 reviews)
"👍"

Reviewed on Dec 19, 2024

Mount Snow Grand Summit Resort
The Covered Bridge Inn
The Covered Bridge Inn
2.5 out of 5
1043 Putney Road, Brattleboro, VT
The price is $187 per night from Jan 7 to Jan 8
$187
includes taxes & fees
Jan 7 - Jan 8
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8/10 Very Good! (1,001 reviews)
"Everything is right there I mean literally everything was right there"

Reviewed on Dec 14, 2024

The Covered Bridge Inn
Comfort Inn & Suites Brattleboro I-91
Comfort Inn & Suites Brattleboro I-91
2.5 out of 5
1186 Putney Road, Brattleboro, VT
The price is $114 per night from Jan 8 to Jan 9
$114
includes taxes & fees
Jan 8 - Jan 9
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
8.6/10 Excellent! (547 reviews)
"Price and quality makes it great"

Reviewed on Jan 3, 2025

Comfort Inn & Suites Brattleboro I-91
The Putney Inn
The Putney Inn
2.5 out of 5
57 Putney Landing Rd, Putney, VT
The price is $102 per night from Jan 7 to Jan 8
$102
includes taxes & fees
Jan 7 - Jan 8
Book a stay at this business-friendly motel in Putney. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
8.2/10 Very Good! (1,002 reviews)
"The check in staff was very friendly. We arrived late in the evening. Room was clean and quiet. It was a last minute stay before heading to a ski hill. It worked out well for the price."

Reviewed on Jan 4, 2025

The Putney Inn
See all 1,212 properties in Jacksonville
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.