Cheap Flights to Monroe County from $24 (2026/2027)

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Jet to one of Monroe County's top cities

How Much Does it Cost To Fly To Monroe County?

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

OriginDestinationTravel DatesFlights From*
CLTMiamiDecember 7 to December 10$48
ATLMiamiNovember 17 to November 20$53
PIEKey WestDecember 2 to December 3$82
PHLMiamiJanuary 8 to January 17$98
TPAMiamiDecember 30 to December 31$132
EWRMiamiJanuary 27 to February 1$192
BOSMiamiJanuary 12 to January 13$199
SWFKey WestJanuary 13 to January 20$203
CLTKey WestDecember 7 to December 12$259
BOSKey WestFebruary 1 to February 8$267
BWIKey WestJanuary 21 to January 25$369
ATLKey WestDecember 12 to December 15$369
EWRKey WestDecember 17 to December 21$376
DTWKey WestDecember 16 to January 6$380
PHLKey WestFebruary 6 to February 13$513
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
ATLMiamiNovember 6 to November 9$78
PIEKey WestNovember 7 to November 11$86
CLTMiamiNovember 8 to November 9$87
BWIMiamiNovember 6 to November 7$138
PHLMiamiNovember 7 to November 14$212
DTWMiamiNovember 6 to November 10$248
TPAMiamiNovember 7 to November 17$287
MDWMiamiNovember 7 to November 9$338
LGAMiamiNovember 7 to November 14$341
BOSMiamiNovember 8 to November 16$406
BOSKey WestNovember 6 to November 11$603
EWRKey WestNovember 8 to November 11$605
EWRKey WestNovember 8 to November 11$605
ATLKey WestNovember 6 to November 9$927
PHLKey WestNovember 8 to November 15$1,348
*Prices include taxes and fees

Best Monroe County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
President Hotel Villa
Avi Lux Stay
The Retreat Collection at 1 Hotel & Homes South Beach
Don't see what you're looking for?
See all available trips from Boston to Monroe County
View all trips

Travelers ❤️ These Monroe County 🏨

Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Book a stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Florida Keys Brewing Co. and Lorelei Restaurant & Cabana Bar are located nearby.
9.2/10 Wonderful! (1,499 reviews)
"Nice hotel, great service"

Reviewed on Nov 2, 2026

Opens in a new windowCheeca Lodge & Spa
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Blvd Key West FL
Book a stay at this beach hotel in Key West. Enjoy breakfast (surcharge), a free airport shuttle, and room service. Our guests praise the pool and the restaurant in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
8.8/10 Excellent! (1,812 reviews)
"Kind and friendly service. Great pool, room was small but maximized its space. Free internet. Air conditioning worked well. No laundry service available unfortunately for longer stays."

Reviewed on Nov 2, 2026

Opens in a new windowMargaritaville Beach House Key West
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
9/10 Wonderful! (1,901 reviews)
"The property closed for renovations and moved us to another hotel."

Reviewed on Nov 2, 2026

Opens in a new windowHavana Cabana at Key West
Save an average of 15% on thousands of hotels when you're signed in
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
Book a stay at this family-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
8.6/10 Excellent! (2,771 reviews)
"Very nice resort. Pool was great. Food was great as well. Bed was wonderful. Staff was very helpful and friendly. Shuttle made it excellent for getting to Old Town. The whole stay was the best…and we have traveled to all 50 states and 28 countries. Thank you!!"

Reviewed on Nov 2, 2026

Opens in a new windowBlue Flamingo Resort Key West
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.

Frequently asked questions

How much is the cheapest flight to Monroe County?
A roundtrip flight to Monroe County cost as little as $48 in the last seven days. Once you've chosen your travel dates, we'll help you grab an amazing deal. This price was available on Travelocity for flights to Monroe County departing within the next year. Prices and availability are subject to change. Additional terms apply.
What is the cheapest month to fly to Monroe County?
Be sure to leave January clear in your calendar, because it's the cheapest month to head to Monroe County. That's based on Travelocity's direct flight demand from January to December last year. With more money in your wallet, you can go on a shopping binge, go to a concert or whatever else you like!
How can I check my flight status to Monroe County?
There are a few ways you can check the status of your flight. You'll find all the necessary info in our "Trips" portal, which is located at the top right of our homepage. Sign in or create a new account in seconds — you can then view and make changes to your bookings whenever you want to. For those on the move, the Travelocity app can also help you check the status of your flight to Monroe County, as well as share details with any members of your family flying with you.
How do I find the best deals on flights to Monroe County?
It pays to book in advance, and if you can, avoid traveling during high season. Another smart way to save is by clicking the "Flexible dates" box at the top of the page after searching for your flights. This will reveal ticket prices for surrounding days. In the last seven days, the lowest price for a roundtrip flight to Monroe County was $48. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Monroe County with Travelocity?
Search for cheap flights to Monroe County with Travelocity and begin arranging your next getaway. With round-the-clock customer support during every stage of your trip and a Price Match Guarantee, we take the worry out of reserving cheap family flights, hotels, experiences and more. Bag a fantastic deal today and brace yourself for an epic adventure.
What are the most popular flight routes to Monroe County?
Browse through these major flight routes to Monroe County and start planning your next big adventure:

  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Key West Intl. Airport (EYW) - 849 flights a month.
  • Miami, FL (MIA-Miami Intl.) to Key West Intl. Airport (EYW) - 637 flights a month.
  • Charlotte, NC (CLT-Charlotte-Douglas Intl.) to Key West Intl. Airport (EYW) - 442 flights a month.

How much is a flight to Monroe County on average?
Travelers have found roundtrip flights to Monroe County for between $48 and $1,348 with Travelocity in the last seven days. Whether you're planning to fly economy or business class, we'll help you get a fabulous deal. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
How long is the average flight to Monroe County?
Take a look at these main routes to get an idea on how long you'll be in your seat during a direct flight to Monroe County:

  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Key West Intl. Airport (EYW) - 1 hour and 45 minutes
  • Miami, FL (MIA-Miami Intl.) to Key West Intl. Airport (EYW) - 48 minutes
  • Charlotte, NC (CLT-Charlotte-Douglas Intl.) to Key West Intl. Airport (EYW) - 2 hours and 5 minutes

What can I expect on a flight to Monroe County?
This mostly depends on where you're flying from and which airline you go with. You'll likely find all types of flights to Monroe County, from business fares to cheap flights for family vacations. If a flight is classed as long haul, the airline will usually offer meals and drinks, a range of entertainment programs as well as games to amuse the kids.

Explore More Ways to Travel with Travelocity