Cheap Flights to Monroe County from $25 (2026/2027)| Travelocity

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Key West

Flights

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.

Wed, Nov 11 - Wed, Nov 11

ATL

Hartsfield-Jackson Atlanta Intl.

MIA

Miami Intl.

$43

Roundtrip

found 2 days ago

Wed, Oct 14 - Wed, Oct 21

BWI

Baltimore Washington Intl. Thurgood Marshall

MIA

Miami Intl.

$54

Roundtrip

found 2 days ago

Tue, Nov 3 - Tue, Nov 10

PHL

Philadelphia Intl.

MIA

Miami Intl.

$109

Roundtrip

found 4 hours ago

Mon, Nov 23 - Thu, Dec 3

PHL

Philadelphia Intl.

MIA

Miami Intl.

$124

Roundtrip

found 1 day ago

Sun, Nov 8 - Thu, Nov 12

LAX

Los Angeles Intl.

MIA

Miami Intl.

$190

Roundtrip

found 12 hours ago

Sun, Dec 6 - Fri, Dec 11

SFO

San Francisco Intl.

MIA

Miami Intl.

$280

Roundtrip

just found

Tue, Dec 1 - Sat, Dec 5

LAX

Los Angeles Intl.

EYW

Key West Intl.

$380

Roundtrip

found 3 days ago

Fri, Oct 23 - Thu, Oct 29

SFO

San Francisco Intl.

EYW

Key West Intl.

$404

Roundtrip

found 2 days ago

Sat, Jan 9 - Tue, Jan 19

PHL

Philadelphia Intl.

AVT

Aventura Brightline Train Station

$424

Roundtrip

found 21 hours ago

Sat, Jan 9 - Tue, Jan 19

PHL

Philadelphia Intl.

EKW

Miami Central Brightline Train Station

$424

Roundtrip

found 21 hours ago

Origin	Destination	Travel Dates	Flights From*
BWI	Miami	November 10 to November 11	$44
PIE	Key West	October 17 to October 21	$86
TPA	Miami	October 27 to October 28	$109
PHL	Miami	December 4 to December 6	$123
EWR	Miami	November 10 to November 12	$190
CLT	Miami	October 29 to November 2	$191
DTW	Miami	November 7 to November 10	$196
ORD	Key West	December 4 to December 7	$313
JFK	Key West	December 7 to December 16	$335
EWR	Key West	October 27 to October 31	$344
ATL	Key West	December 22 to December 26	$349
DTW	Key West	December 8 to December 16	$353
BOS	Key West	October 18 to October 22	$372
PHL	Key West	December 12 to December 15	$493
CLT	Key West	January 9 to January 12	$526

*Prices include taxes and fees

Origin	Destination	Travel Dates	Flights From*
PIE	Key West	October 10 to October 17	$86
ATL	Miami	October 10 to October 13	$192
TPA	Miami	October 10 to October 13	$234
CLT	Miami	October 11 to October 12	$270
EWR	Miami	October 10 to October 17	$359
EWR	Miami	October 10 to October 17	$359
PHL	Miami	October 11 to October 19	$375
BWI	Key West	October 11 to October 18	$434
EWR	Key West	October 10 to October 17	$439
EWR	Key West	October 10 to October 17	$439
BOS	Miami	October 10 to October 14	$469
BOS	Key West	October 9 to October 16	$469
ORD	Key West	October 10 to October 11	$537
ATL	Key West	October 10 to October 17	$637
DTW	Key West	October 10 to October 11	$735

*Prices include taxes and fees

Best Monroe County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.

3.5-star property

Cavalier Hotel South Beach

Dec 9 - Dec 13

4 night stay

Boston (BOS) to Miami (MIA)

Delta • Coach

Miami (MIA) to Boston (BOS)

Allegiant Air • Coach

Save 100% on your flight

$415

per person

found 1 day ago

3.0-star property

Ithaca Hotel

Oct 16 - Oct 20

4 night stay

Baltimore (BWI) to Miami (MIA)

American Airlines • Coach

Miami (MIA) to Baltimore (BWI)

Frontier Airlines • Coach

$850

per person

found 1 day ago

5.0-star property

The Retreat Collection at 1 Hotel & Homes South Beach

Oct 18 - Oct 22

4 night stay

Boston (BOS) to Miami (MIA)

Allegiant Air • Roundtrip • Coach

$6,785

per person

found 1 day ago

Don't see what you're looking for?

See all available trips from Boston to Monroe County

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Travelers ❤️ These Monroe County 🏨

Cheeca Lodge & Spa

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.

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. Popular attractions History of Diving Museum and Windley Key Fossil Reef Geological State Park are located nearby.

Blue Flamingo Resort Key West

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 Smathers Beach are located nearby.

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Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Book a stay at this spa hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and South Beach are located nearby.

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.

More Ways To Wander Monroe County

Monroe County Hotels

Find the perfect hotel after your flight

Monroe County Vacation Rentals

Great Deals on alternative accommodations

Monroe County Car Rentals

Affordable cars to get you around town

Monroe County Vacations

Save more by combining flights, hotels and cars

Things to do in Monroe County

Activities, attractions and tours

Frequently asked questions

How much is the cheapest flight to Monroe County?

A roundtrip flight to Monroe County cost as little as $43 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 November 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 $43. 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 $43 and $735 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.

Cheap Flights to Monroe County from $25 (2026/2027)

Travelers

Jet to one of Monroe County's top cities

Key West

Key Largo

Marathon

Islamorada

Summerland Key

Tavernier

How Much Does it Cost To Fly To Monroe County?

Best Monroe County Flight and Hotel Packages

Cavalier Hotel South Beach

Dec 9 - Dec 13

Boston (BOS) to Miami (MIA)

Miami (MIA) to Boston (BOS)

Ithaca Hotel

Oct 16 - Oct 20

Baltimore (BWI) to Miami (MIA)

Miami (MIA) to Baltimore (BWI)

The Retreat Collection at 1 Hotel & Homes South Beach

Oct 18 - Oct 22

Boston (BOS) to Miami (MIA)

Travelers ❤️ These Monroe County 🏨

Cheeca Lodge & Spa

Chesapeake Beach Resort

Blue Flamingo Resort Key West

Southernmost Beach Resort and Guesthouses

More Ways To Wander Monroe County

Frequently asked questions

Explore More Ways to Travel with Travelocity