$95 Cheap flights to Monroe County

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Key West

Key West

Cheap flights to Monroe County from $95 One Way, $177 Round Trip

$177 return flights and $95 one-way flights to Monroe County were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Oct 3 - Tue, Oct 6
EWR
New York
MIA
Miami
$177 Roundtrip, just found
$177
Roundtrip
just found
Select United flight, departing Sat, Oct 3 from New York to Miami, returning Tue, Oct 6, priced at $177 just found
Tue, Sep 15 - Wed, Sep 23
LGA
New York
MIA
Miami
$187 Roundtrip, found 3 hours ago
$187
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Tue, Sep 15 from New York to Miami, returning Wed, Sep 23, priced at $187 found 3 hours ago
Sat, Oct 3 - Tue, Oct 6
EWR
New York
MIA
Miami
$187 Roundtrip, just found
$187
Roundtrip
just found
Select American Airlines flight, departing Sat, Oct 3 from New York to Miami, returning Tue, Oct 6, priced at $187 just found
Tue, Sep 15 - Wed, Sep 23
LGA
New York
MIA
Miami
$187 Roundtrip, found 3 hours ago
$187
Roundtrip
found 3 hours ago
Select Delta flight, departing Tue, Sep 15 from New York to Miami, returning Wed, Sep 23, priced at $187 found 3 hours ago
Sat, Aug 29 - Wed, Sep 2
JFK
New York
MIA
Miami
$187 Roundtrip, just found
$187
Roundtrip
just found
Select American Airlines flight, departing Sat, Aug 29 from New York to Miami, returning Wed, Sep 2, priced at $187 just found
Sat, Aug 29 - Wed, Sep 2
JFK
New York
MIA
Miami
$187 Roundtrip, just found
$187
Roundtrip
just found
Select Delta flight, departing Sat, Aug 29 from New York to Miami, returning Wed, Sep 2, priced at $187 just found
Wed, Aug 19 - Wed, Aug 26
LGA
New York
MIA
Miami
$197 Roundtrip, found 3 hours ago
$197
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Wed, Aug 19 from New York to Miami, returning Wed, Aug 26, priced at $197 found 3 hours ago
Tue, Aug 11 - Tue, Aug 18
EWR
New York
MIA
Miami
$210 Roundtrip, found 2 hours ago
$210
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Tue, Aug 11 from New York to Miami, returning Tue, Aug 18, priced at $210 found 2 hours ago
Sun, Dec 13 - Sun, Dec 20
JFK
New York
EYW
Key West
$329 Roundtrip, found 16 hours ago
$329
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Sun, Dec 13 from New York to Key West, returning Sun, Dec 20, priced at $329 found 16 hours ago

Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
ATLMiamiJune 20 to July 4$228
DTWMiamiJune 20 to June 23$292
BOSMiamiJune 19 to June 23$300
EWRKey WestJune 20 to July 1$422
EWRKey WestJune 20 to July 1$422
CLTMiamiJune 20 to June 23$439
LGADowntown MiamiJune 20 to June 27$481
EWRDowntown MiamiJune 21 to July 3$527
BOSKey WestJune 19 to June 22$539
PHLKey WestJune 20 to June 26$551
DTWKey WestJune 21 to June 27$554
CLTKey WestJune 20 to June 25$588
*Prices include taxes and fees

Find The Perfect Hotel For After Your Flight

Score Epic Monroe County Accommodation Deals

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$175 nightly
The price is $197 total per night from Jun 17 to Jun 18
$197 total
Jun 17 - Jun 18
Total with taxes and fees
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 ...
8.4/10 Very Good! (2,401 reviews)
"Everything was very nice and clean!"

Reviewed on Jun 16, 2026

Opens in a new windowBlue Flamingo Resort Key West
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
$266 nightly
The price is $299 total per night from Jun 29 to Jun 30
$299 total
Jun 29 - Jun 30
Total with taxes and fees
Book a stay at this beach 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 ...
8.8/10 Excellent! (3,401 reviews)
"From top to bottom this place was great! The location was nice, very chill vibe in the area, sort of away from the craziness of staying further down Duval St. The staff was great, super nice and accommodating, helpful, and went out of their way you were having a great time and that you felt the accommodations ..."

Reviewed on Jun 16, 2026

Opens in a new windowSouthernmost Beach Resort and Guesthouses
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

3.5 out of 5
3850 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $151 total per night from Jun 22 to Jun 23
$151 total
Jun 22 - Jun 23
Total with taxes and fees
Book a stay at this business-friendly hotel in Key West. Enjoy 2 restaurants, breakfast (surcharge), and a free area shuttle. Our guests praise the pool and ...
8/10 Very Good! (1,242 reviews)
"Great hotel, would stay there again. Lyft rides to Duval were reasonable, but the hotel does offer a free shuttle during specific hours."

Reviewed on Jun 16, 2026

Opens in a new windowHilton Garden Inn Key West / The Keys Collection
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Reefhouse Resort & Marina

Reefhouse Resort & Marina

4.5 out of 5
103800 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
$239 nightly
The price is $264 total per night from Jun 21 to Jun 22
$264 total
Jun 21 - Jun 22
Total with taxes and fees
Book a stay at this luxury hotel in Key Largo. Enjoy free parking, a full-service spa, and 3 restaurants. Our guests praise the pool and the helpful staff in ...
9.4/10 Exceptional! (1,489 reviews)
"Great spot!!!!"

Reviewed on Jun 15, 2026

Opens in a new windowReefhouse Resort & Marina
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.

Need a Car For After Your Flight?

Economy

Chevrolet Spark
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass
  • 5 people
Jeep Compass
SUV Jeep Compass

Monroe County

Get the absolute lowest prices on flights to Monroe County by shopping with Orbitz. Orbitz is the most efficient travel planner around, allowing you to search, compare and book discount domestic and international flights fast. With cutting-edge mobile tools and access to frequent flier rewards programs, we have everything you need for both your routine and holiday excursions.

Book Your Flight To Monroe County Using Your Mobile Device

New mobile app tools enable those with hand-held devices to scout out the best bargains and to secure tickets from any location. If you have an iPhone, iPad or Android device, you may take advantage of special discounts, only available to mobile device customers, when you book hotel rooms or car rentals on the same day as booking Monroe County flights.

Avoid Check-In Hassles When Traveling On Flights to Monroe County

Orbitz also provides an array of resources that can help you eliminate most check-in hassles. Detailed baggage information is continually available for Monroe County flights. Mobile apps can also be used to share travel itineraries with family members or business associates.

Keeping Everyone Up To Date

When you download the free Orbitz mobile phone app, you can get regular and free flight updates. These will keep you informed of important scheduling changes. Updates can even be sent to several contacts, helping to keep everyone current on anticipated arrival times and all other relevant flight details.

Orbitz makes traveling on a budget very easy to do. We provide everything you need to plan your ideal trip from start to finish. Getting there and back again is a snap when you book your Monroe County flight using Orbitz.

Frequently asked questions

Which airlines fly to Monroe County?
There are 18 air carriers that go to Key West Intl. Airport (EYW). With this amount of choice, there's a great chance you'll land a low-cost flight! Your Monroe County vacation awaits with one of these leading domestic carriers:

  • American Airlines - 118 flights to Monroe County per month
  • Silver Airways - 57 flights to Monroe County per month
  • Delta - 45 flights to Monroe County per month

How much is a flight to Monroe County?
If you're looking at round-trip flights, fares ranged from $177 to $588 this last week. The lowest one-way ticket was $95, coming from New York (LGA).
How to book the cheapest flight to Monroe County?
With some of the most exciting flight deals around, a bargain is always waiting for you with Orbitz. The following useful tips will help you find cheap flights to Monroe County — and leave you with more money to play with:

  • Depending on your departure city, click on the 'Nearby airports' function (located under the departure and arrival options). In some cases, other departure points will offer better prices on fares.
  • If your plans aren't set in stone, click on the 'Show flexible dates' link to see the flight deals for multiple departure dates. You may find an amazing fare.
  • You can also select the 'Show options' function to filter results for your preferred airline, seating class, nonstop flights and refundable flights. Under 'Sort & Filter' to the left, you can even choose the time of day you want to fly.
  • The early bird gets the best deals, so book your tickets the moment you know your travel dates. The most affordable fares get snapped up fast and prices increase as the departure date gets closer.
  • Make greater savings on your trip by combining your hotel, flights and car rentals into one convenient package deal. Your travel budget will thank you for it.
  • Flying during the busy season often means costly airfares. If possible, plan your vacation outside of popular dates, such as school breaks, Thanksgiving and Easter.

What is the best time to book a flight to Monroe County?
Land a bargain and book your tickets to Monroe County in January. If you've missed this month, don't worry. February and August often have low airfares available, too. Make sure you don't sleep on a sale though — cheap flights emerge and disappear in the tap of a button!
What day of the week is the cheapest to book a flight to Monroe County?
To pick up an unbeatable flight deal, make a booking on a Tuesday, Wednesday or Saturday. Usually, these are the cheapest days of the week to book seats to Monroe County.
What is the cheapest day of the week to fly to Monroe County?
Think about leaving early in the week to nab cheap flights to Monroe County. Orbitz data from 2020 shows Monday is typically the most affordable day to take off, followed by Tuesday. Saturday was found to have the highest airfares. This is probably because most passengers prefer to kick off their vacation at the end of the week.
What is the cheapest month to fly to Monroe County?
We won't keep you guessing — based on Orbitz data, August is generally the most inexpensive month to fly. Ideal for those who need a weekend getaway or simply escape from it all before the weather changes. Be aware that the least affordable time to fly is the height of summer, with airfares at their highest in June.
Which airlines allow free cancellation?
When searching for flights on Orbitz, choose "Filter by flexible change policies." This filter will show you all the airlines offering free cancellation and no change fees. That means you can relax knowing that if things change, your flight can too.
What do I need for the flight to Monroe County?
There is so much to plan for any big trip, so it's useful to get some help before you set out. Here are a few pointers to ensure that you're ready for your flight:

  • You'll need to take all applicable travel documents and your identification. How much will depend on where you're departing from. When you book, you're encouraged to use the same name, birth date and gender as indicated on your current ID.
  • A well-packed carry-on bag is a must-have for any lengthy flight. With several hours to kill, you'll want something to keep you busy on your trip to Monroe County. We recommend a good book or magazine, and something to snack on.
  • Plane cabins are frequently quite cold. Even if you're traveling during the height of the Monroe County summer, be sure to carry some warm clothes with you.

How do I get cheap first-class/business deals to Monroe County?
There are ways of booking first or business-class fares to Monroe County that won't burn through your savings. Find a seat in the pointy end of the plane for less with these practical tips:

  • Flexibility is essential. By being open to other travel dates, you'll have a better chance of picking up a deal on business or first-class airfares.
  • Low-cost airlines offer business-class seats at more affordable prices. Skip the full-service carriers and consider these cheaper options.
  • Bid for an upgrade in online auctions or upgrade your seat with loyalty points.

What is the best time to go to Monroe County?
If you want to soak up the culture of Monroe County in the busy season, January, February and March are the best months to visit. June 20 signals the beginning of summertime in the Northern Hemisphere and is a fantastic time to travel if you're hooked on the open air. At this time, average daily temperatures normally range from 80 ºF to 85 ºF.

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.