Cheap flights To Lower Sugarloaf Key (EYW) from $40

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

Cheap Flights to Lower Sugarloaf Key from $40 One Way, $79 Round Trip

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

Mon, Apr 27 - Wed, May 6
TPA
Tampa Intl.
EYW
Key West Intl.
$79 Roundtrip, found 4 hours ago
$79
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Mon, Apr 27 from Tampa Intl. to Key West Intl., returning Wed, May 6, priced at $79 found 4 hours ago
Sun, May 31 - Fri, Jun 5
MCO
Orlando Intl.
EYW
Key West Intl.
$102 Roundtrip, found 3 hours ago
$102
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Sun, May 31 from Orlando Intl. to Key West Intl., returning Fri, Jun 5, priced at $102 found 3 hours ago
Wed, Sep 9 - Wed, Sep 16
CHS
Charleston Intl.
EYW
Key West Intl.
$142 Roundtrip, found 1 day ago
$142
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Sep 9 from Charleston Intl. to Key West Intl., returning Wed, Sep 16, priced at $142 found 1 day ago
Wed, Aug 19 - Thu, Aug 20
ORF
Norfolk Intl.
EYW
Key West Intl.
$142 Roundtrip, found 1 day ago
$142
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Aug 19 from Norfolk Intl. to Key West Intl., returning Thu, Aug 20, priced at $142 found 1 day ago
Thu, Aug 27 - Wed, Sep 2
RDU
Raleigh - Durham Intl.
EYW
Key West Intl.
$147 Roundtrip, found 3 days ago
$147
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Aug 27 from Raleigh - Durham Intl. to Key West Intl., returning Wed, Sep 2, priced at $147 found 3 days ago
Sun, Aug 23 - Wed, Aug 26
CAK
Akron-Canton
EYW
Key West Intl.
$149 Roundtrip, found 1 day ago
$149
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sun, Aug 23 from Akron-Canton to Key West Intl., returning Wed, Aug 26, priced at $149 found 1 day ago
Mon, Aug 24 - Wed, Sep 2
BDL
Bradley Intl.
EYW
Key West Intl.
$156 Roundtrip, just found
$156
Roundtrip
just found
Select Breeze Airways flight, departing Mon, Aug 24 from Bradley Intl. to Key West Intl., returning Wed, Sep 2, priced at $156 just found
Mon, Apr 13 - Tue, Apr 14
FLL
Fort Lauderdale - Hollywood Intl.
EYW
Key West Intl.
$164 Roundtrip, found 6 days ago
$164
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Mon, Apr 13 from Fort Lauderdale - Hollywood Intl. to Key West Intl., returning Tue, Apr 14, priced at $164 found 6 days ago
Mon, May 25 - Wed, Jun 3
PVD
T.F. Green
EYW
Key West Intl.
$200 Roundtrip, found 1 hour ago
$200
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Mon, May 25 from T.F. Green to Key West Intl., returning Wed, Jun 3, priced at $200 found 1 hour ago
Sun, Apr 12 - Thu, Apr 16
DFW
Dallas-Fort Worth Intl.
EYW
Key West Intl.
$237 Roundtrip, found 4 days ago
$237
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Sun, Apr 12 from Dallas-Fort Worth Intl. to Key West Intl., returning Thu, Apr 16, priced at $237 found 4 days ago

Lower Sugarloaf Key Flight Information

Traveling To
Lower Sugarloaf Key
Destination Airport IATA Code
EYW
Number of Airlines Serving
Airlines
Breeze Airways, Spirit Airlines
Flight Price
$79
Earliest Departing Flight
Latest Departing Flight

Book Your Flight & Hotel Together & Save

Lower Sugarloaf Key economy flight packages

Price found within the past 48 hours. Click for updated prices.
Cavalier Hotel South Beach
3.5-star property

Cavalier Hotel South Beach

May 7 - May 11

4 night stay

Boston (BOS) to Miami (MIA)

Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,332, price is now $792 per person
$792
per person
found 1 day ago
Villas At Hawks Cay Resort
4.0-star property

Villas At Hawks Cay Resort

May 10 - May 15

5 night stay

Boston (BOS) to Miami (MIA)

Delta • Non-stop • Coach

Miami (MIA) to Boston (BOS)

American Airlines • Non-stop • Coach
Price was $2,459, price is now $1,545 per person
$1,545
per person
found 7 hours ago
Don't see what you're looking for?
See all available trips from Boston to Lower Sugarloaf Key
View all trips

Lower Sugarloaf Key premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Miami Beach
4.0-star property

Hotel Riu Plaza Miami Beach

8/10 Very Good! (1,165 reviews)

May 17 - May 22

5 night stay

Newark Liberty Intl. Airport (EWR) to Miami (MIA)

Spirit Airlines • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,366, price is now $968 per person
$968
per person
found 22 hours ago
The hotel is clean. The staff will greet you but not immediately. The rooms are ok but the beds are small and everything is built for shorter stature people. I am average and the beds and toilet are short! TV's are older. Everything is average and ok.

Reviewed on Jan 19, 2026

Carillon Miami Wellness Resort
5.0-star property

Carillon Miami Wellness Resort

8.8/10 Excellent! (787 reviews)

May 17 - May 22

5 night stay

Newark Liberty Intl. Airport (EWR) to Miami (MIA)

Spirit Airlines • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,147, price is now $1,429 per person
$1,429
per person
found 22 hours ago
Pretty good spot to stay in

Reviewed on Oct 1, 2021

Don't see what you're looking for?
See all available trips from Newark Liberty Intl. Airport to Lower Sugarloaf Key
View all trips

Lower Sugarloaf Key first class flight packages

Price found within the past 48 hours. Click for updated prices.
Creekside Inn
2.5-star property

Creekside Inn

7.8/10 Good! (1,027 reviews)

May 15 - May 20

5 night stay

Boston (BOS) to Miami (MIA)

Delta • FirstClass

Miami (MIA) to Boston (BOS)

United • FirstClass
Price was $2,417, price is now $1,547 per person
$1,547
per person
found 20 hours ago
Leaving a review to let Travellers know that this place deserves a better rating and reviews than what some Travellers have left. We had a great stay! The property is older and could use some upgrades but it was exactly suited for our stay. Property is right on a canal where you can see Tarpon, Manatees and other fish, if you have a boat you can dock right there. Our stay was quiet and peaceful and housekeeping took care of any needs we had. Its within walking distance of a few restaurants, dive shop, bait shop, snorkel tour. I would recommend Lido73, Mar Bar and Old Tavernier restaurants all within walking distance. Just know it not the 4 seasons just and older property that will suit your needs. I would definitely come stay again.

Reviewed on Mar 22, 2026

The Key West Hotel
2.5-star property

The Key West Hotel

9.2/10 Wonderful! (536 reviews)

May 16 - May 23

7 night stay

Newark Liberty Intl. Airport (EWR) to Key West (EYW)

United • Roundtrip • FirstClass
Save 100% on your flight
Price was $6,002, price is now $3,591 per person
$3,591
per person
found 18 hours ago
Gorgeous property right on Duval Street but hidden from the noise and bustle. Convenient to everything you want to do and see. Wonderfully helpful and friendly staff.

Reviewed on Jan 5, 2025

Hyatt Vacation Club at Windward Pointe, Key West
3.5-star property

Hyatt Vacation Club at Windward Pointe, Key West

9.4/10 Exceptional! (1,020 reviews)

May 16 - May 23

7 night stay

Newark Liberty Intl. Airport (EWR) to Key West (EYW)

United • Roundtrip • FirstClass
Price was $3,335, price is now $2,299 per person
$2,299
per person
found 18 hours ago
Staff was fantastic, room and grounds very clean and well kept.

Reviewed on Feb 12, 2026

Don't see what you're looking for?
See all available trips from Boston to Lower Sugarloaf Key
View all trips

Frequently asked questions

How much is a flight to Lower Sugarloaf Key?
Return fares dipped as low as $79 this past week to Lower Sugarloaf Key, and peaked at $237. Jet-setters departing Tampa (TPA) managed to bag one-way tickets starting from just $40.
How to book the cheapest flight to Lower Sugarloaf Key?
Snapping up cheap flights to Lower Sugarloaf Key is as easy as booking your ticket with Orbitz. But if you'd love to make sure you're walking away with the best flight deals around, here are a few tips to keep in mind:

  • Departing from or arriving at other airports may help you save on airfares. Type in your preferred departure and arrival airports. Next, click on the 'Nearby airports' function below to see what your options are.
  • If you're flexible with your schedule, click on the 'Show flexible dates' link. It'll bring up flight deals for the days before and after your selected departure. Ticket prices often vary depending on what day it is.
  • Hit 'Show options' to refine your search results. You can choose 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 best deals, so book as soon as you've worked out your travel dates. The cheapest airfares sell out quickly and prices generally climb as the departure date nears.
  • Consider bundling your hotels, flights and car rental into an Orbitz package to make your budget go even further.
  • Don't fly during peak seasons if possible. By avoiding summer and school vacations, you can make superb savings on your airfares.

What is the best time to book a flight to Lower Sugarloaf Key?
If possible, book your flights to Lower Sugarloaf Key in January. This is the best month to reserve low airfares, followed by February and August. With a bit of patience and planning, you're bound to find a cheap flight with Orbitz.
What day of the week is the cheapest to book a flight to Lower Sugarloaf Key?
When it comes to cheap airfares to Lower Sugarloaf Key, the best days to book are generally Tuesdays, Wednesdays and Saturdays. An unbeatable flight deal is just a few clicks away with Orbitz.
What is the cheapest day of the week to fly to Lower Sugarloaf Key?
Look into leaving early in the week to score cheap flights to Lower Sugarloaf Key. Orbitz data from 2020 suggests Monday is generally the most inexpensive day to set off, followed by Tuesday. Saturdays were shown to have the highest airfares. This is possibly because many passengers prefer to start their trip when the weekend rolls around.
What is the cheapest month to fly to Lower Sugarloaf Key?
Get set to jet for less in August. This is generally an excellent month to take off if you want cheap flights to Lower Sugarloaf Key, according to Orbitz data. The most expensive time to take off is June, so avoid this month if possible.
Which airlines allow free cancellation?
If you're concerned your travel plans may change, Orbitz will help you find a flexible fare. All you need to do is select "Filter by flexible change policies" when searching for your perfect flight. We'll show you all the airlines that include free cancellation within 24 hours and no change fees — all on top of irresistibly low prices.
What do I need for the flight to Lower Sugarloaf Key?
From onboard activities to travel necessities like noise-canceling headphones, there are several things a frequent flyer always carries with them. To make sure you're prepared for your journey, have a look at this helpful list:

  • Check that you've packed your travel papers and identification. For international trips, you'll need to bring your passport. When you book your flights, always use the same name, gender and birth date as written on your current ID.
  • A well-stocked carry-on bag is a must-have for any lengthy flight. With several hours to kill, you'll want something to keep you occupied while in the air. We recommend a good book (or trashy magazine), and something to nosh on.
  • Air conditioning and high altitudes can produce a cold environment. No matter what the season is in Lower Sugarloaf Key, bring a sweater along to keep nice and warm during your flight.

How do I get cheap first-class/business deals to Lower Sugarloaf Key?
There are ways of booking first or business-class tickets to Lower Sugarloaf Key that won't burn through your budget. Find a seat at the front of the plane for less with these great tips:

  • Flexibility isn't just for the gym. Leave some room to move around your travel dates so you can snap up cheaper airfares when they crop up.
  • Look for a low-cost airline that offers seats in business class. They usually come with extra space and a glass of bubbly — and a more attractive price.
  • Bid for an upgrade in online auctions or upgrade your fare through your flight loyalty scheme.

What is the best time to go to Lower Sugarloaf Key?
You'll have tons of fun no matter what time of year you go to Lower Sugarloaf Key, but February, March and November are the busiest months. Like to fill up your itinerary with warm-weather adventures? Book your trip around June 20. This is when summertime starts in the Northern Hemisphere. Expect the mercury to range between 80 ºF and 85 ºF at this time.

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.