$88 Cheap flights to Monroe County

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Top places to visit in Monroe County

A beach with palm trees, people sunbathing, and a resort in the background.
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Key West

Key West

Cheap flights to Monroe County from $88 One Way, $86 Round Trip

$86 return flights and $88 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.

Tue, Oct 20 - Tue, Oct 27
EWR
New York
MIA
Miami
$179 Roundtrip, found 2 hours ago
$179
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Tue, Oct 20 from New York to Miami, returning Tue, Oct 27, priced at $179 found 2 hours ago
Fri, Oct 23 - Sun, Oct 25
JFK
New York
MIA
Miami
$243 Roundtrip, just found
$243
Roundtrip
just found
Select American Airlines flight, departing Fri, Oct 23 from New York to Miami, returning Sun, Oct 25, priced at $243 just found
Wed, Jan 13 - Thu, Jan 14
SFO
San Francisco
MIA
Miami
$264 Roundtrip, found 5 days ago
$264
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Jan 13 from San Francisco to Miami, returning Thu, Jan 14, priced at $264 found 5 days ago
Tue, Dec 8 - Tue, Dec 22
JFK
New York
EYW
Key West
$335 Roundtrip, found 4 hours ago
$335
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Tue, Dec 8 from New York to Key West, returning Tue, Dec 22, priced at $335 found 4 hours ago
Wed, Jan 6 - Wed, Mar 10
EWR
New York
EYW
Key West
$339 Roundtrip, found 2 days ago
$339
Roundtrip
found 2 days ago
Select United flight, departing Wed, Jan 6 from New York to Key West, returning Wed, Mar 10, priced at $339 found 2 days ago
Sat, Oct 17 - Wed, Oct 21
SFO
San Francisco
EYW
Key West
$373 Roundtrip, found 2 days ago
$373
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Oct 17 from San Francisco to Key West, returning Wed, Oct 21, priced at $373 found 2 days ago
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Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
PIEKey WestSeptember 27 to September 30$86
ATLMiamiSeptember 27 to September 28$183
CLTMiamiSeptember 26 to September 29$222
PHLMiamiSeptember 27 to September 29$235
BWIMiamiSeptember 26 to October 1$245
TPAMiamiSeptember 26 to October 4$297
LGAMiamiSeptember 26 to September 29$322
DTWMiamiSeptember 26 to September 27$408
ORDMiamiSeptember 26 to September 27$409
EWRMiamiSeptember 26 to September 28$462
EWRKey WestSeptember 26 to September 28$499
EWRKey WestSeptember 26 to September 28$499
BOSKey WestSeptember 25 to September 28$535
CLTKey WestSeptember 25 to September 28$664
DTWKey WestSeptember 25 to September 27$832
*Prices include taxes and fees

Find The Perfect Hotel For After Your Flight

Score Epic Monroe County Accommodation Deals

Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
$190 nightly
The price is $214 total per night from Sep 23 to Sep 24
$214 total
Sep 23 - Sep 24
Total with taxes and fees
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 ...
9.2/10 Wonderful! (1,442 reviews)
"Loved the room, quiet vibe, designated parking, the water front area, and staff. Nice surrounding area. You need a car if you want to go to Key West or nearby cities. If you want activity recommend planning ahead. We were celebrating wedding anniversary and this fit the bill. Loved it and would come ..."

Reviewed on Sep 21, 2026

Opens in a new windowCheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$187 nightly
The price is $210 total per night from Oct 21 to Oct 22
$210 total
Oct 21 - Oct 22
Total with taxes and fees
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. ...
9.2/10 Wonderful! (1,779 reviews)
"Todo"

Reviewed on Sep 20, 2026

Opens in a new windowChesapeake Beach Resort
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
$225 nightly
The price is $253 total per night from Sep 28 to Sep 29
$253 total
Sep 28 - Sep 29
Total with taxes and fees
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 ...
Opens in a new windowSouthernmost Beach Resort and Guesthouses
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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
$160 nightly
The price is $180 total per night from Sep 22 to Sep 23
$180 total
Sep 22 - Sep 23
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 ...
8.6/10 Excellent! (2,681 reviews)
"Was a great place beds could use a little upgrade"

Reviewed on Sep 20, 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.

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

When you plan to buy tickets for flights to Monroe County, you don’t have to look any further than Orbitz! We offer bargain rates and low fares on thousands of flights.

Reliable Customer Service

Along with our low prices, Orbitz is well known for exceptional customer care. We make it simple to find the best Monroe County flights for you. If you need to cancel your booking or change your flight plans, simply contact our Customer Service department to make any adjustments.

Bargain Tickets for Monroe County Flights

Orbitz offers deeply discounted flights to Monroe County, and we provide the resources to research your travel destination and plan your complete itinerary.

Use Orbitz to Earn Points with Your Frequent Flyer Program

Saving your frequent flyer miles for your flights to Monroe County? You can use Orbitz to make your budget ticket reservation for all your flights and still earn points or miles on your frequent flyer program! Just enter your program account number while you’re booking your ticket to have your points added automatically, every time you book with Orbitz.

Convenient Travel Planning Services

If you like the ease of making your travel plans on the move, you’ll love the free Orbitz apps for iPhones, iPads, and Android devices. You can use these apps to review your travel reservations or make a change to your itinerary. Orbitz also offers additional travel assistance such as free mobile alerts that keep you up-to-date about sudden changes to your upcoming flights. You can also browse Orbitz easily on your smartphone by using the mobile version of the website to find budget Monroe County flights.

Frequently asked questions

Which airlines fly to Monroe County?
There are 12 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 $86 to $832 this last week. The lowest one-way ticket was $88, coming from New York (EWR).
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.