$105 Cheap flights to Monroe County

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Top places to visit in Monroe County

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Key West

Key West

Cheap flights to Monroe County from $105 One Way, $163 Round Trip

$163 return flights and $105 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.

Wed, Sep 9 - Wed, Sep 30
JFK
New York
MIA
Miami
$189 Roundtrip, found 4 hours ago
$189
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Wed, Sep 9 from New York to Miami, returning Wed, Sep 30, priced at $189 found 4 hours ago
Wed, Sep 9 - Sat, Sep 12
EWR
New York
MIA
Miami
$189 Roundtrip, found 2 hours ago
$189
Roundtrip
found 2 hours ago
Select United flight, departing Wed, Sep 9 from New York to Miami, returning Sat, Sep 12, priced at $189 found 2 hours ago
Sat, Sep 12 - Sat, Sep 19
LGA
New York
MIA
Miami
$192 Roundtrip, found 1 hour ago
$192
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Sat, Sep 12 from New York to Miami, returning Sat, Sep 19, priced at $192 found 1 hour ago
Wed, Oct 21 - Fri, Oct 23
SFO
San Francisco
MIA
Miami
$220 Roundtrip, just found
$220
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, Oct 21 from San Francisco to Miami, returning Fri, Oct 23, priced at $220 just found
Tue, Dec 1 - Tue, Dec 8
JFK
New York
EYW
Key West
$295 Roundtrip, found 2 hours ago
$295
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Tue, Dec 1 from New York to Key West, returning Tue, Dec 8, priced at $295 found 2 hours ago
Tue, Jan 26 - Tue, Feb 9
LGA
New York
EYW
Key West
$319 Roundtrip, found 17 hours ago
$319
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Tue, Jan 26 from New York to Key West, returning Tue, Feb 9, priced at $319 found 17 hours ago
Tue, Oct 6 - Tue, Oct 13
EWR
New York
EYW
Key West
$323 Roundtrip, found 1 hour ago
$323
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Tue, Oct 6 from New York to Key West, returning Tue, Oct 13, priced at $323 found 1 hour ago
Sat, Nov 14 - Thu, Nov 19
SFO
San Francisco
EYW
Key West
$340 Roundtrip, found 17 hours ago
$340
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Sat, Nov 14 from San Francisco to Key West, returning Thu, Nov 19, priced at $340 found 17 hours ago
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Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
BWIMiamiAugust 15 to August 19$163
CLTMiamiAugust 14 to August 17$200
TPAMiamiAugust 15 to August 28$226
PHLMiamiAugust 15 to August 18$255
DTWMiamiAugust 15 to August 22$281
BOSKey WestAugust 16 to August 19$302
EWRMiamiAugust 16 to August 18$337
EWRMiamiAugust 16 to August 18$337
BOSMiamiAugust 14 to August 22$444
LGAKey WestAugust 15 to August 18$462
ORDKey WestAugust 15 to August 17$478
PHLKey WestAugust 15 to August 21$568
CLTKey WestAugust 16 to August 23$623
ATLKey WestAugust 15 to August 20$678
DTWKey WestAugust 16 to August 18$862
*Prices include taxes and fees

Find The Perfect Hotel For After Your Flight

Score Epic Monroe County Accommodation Deals

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
$203 nightly
The price is $228 total per night from Sep 1 to Sep 2
$228 total
Sep 1 - Sep 2
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 ...
Opens in a new windowSouthernmost Beach Resort and Guesthouses
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$184 nightly
The price is $207 total per night from Aug 18 to Aug 19
$207 total
Aug 18 - Aug 19
Total with taxes and fees
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 2 restaurants, and a private beach. Our guests praise the pool and the helpful staff in our reviews. ...
8.6/10 Excellent! (2,409 reviews)
"Specious rooms"

Reviewed on Aug 7, 2026

Opens in a new windowBeachside Resort & Residences
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
$204 nightly
The price is $229 total per night from Aug 18 to Aug 19
$229 total
Aug 18 - Aug 19
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 ...
Opens in a new windowCheeca Lodge & Spa
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Isla Bella Beach Resort & Spa

Isla Bella Beach Resort & Spa

5 out of 5
1 Knights Key Boulevard Marathon FL
Fully refundableReserve now, pay when you stay
$255 nightly
The price is $287 total per night from Aug 18 to Aug 19
$287 total
Aug 18 - Aug 19
Total with taxes and fees
Book a stay at this luxury hotel in Marathon. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
Opens in a new windowIsla Bella Beach Resort & Spa
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?

Standard SUV

Chevrolet Equinox
  • 5 people
  • Unlimited mileage
Key West, Florida, USA
Chevrolet Equinox

$37

$126 total
found 4 days ago
Standard SUV Chevrolet Equinox

Mini Van

Chrysler Pacifica
  • 7 people
  • Unlimited mileage
Key West, Florida, USA
Chrysler Pacifica

$39

$131 total
found 4 days ago
Mini Van Chrysler Pacifica

Special

Managers Special
  • 4 people
  • Unlimited mileage
Key West, Florida, USA
Managers Special

$51

$160 total
found 4 days ago
Special Managers Special

Economy

Mitsubishi Mirage
  • 4 people
  • Unlimited mileage
Key West, Florida, USA
Mitsubishi Mirage

$52

$182 total
found 4 days ago
Economy Mitsubishi Mirage
Lowest prices found within the past 4 days. Prices and availability subject to change. Additional terms may apply.

Monroe County

Why search for low cost fares on your flights to Monroe County when Orbitz offers the guaranteed lowest prices on foreign and domestic flights? When you travel with Orbitz you can benefit from:

Bargain Flights to Monroe County

Orbitz offers massive discounts and substantial last-minute savings on your Monroe County flights. Orbitz ensures that you can find, plan and reserve your flights any destination with ease, all while enjoying the guaranteed lowest prices available anywhere.

Cutting-Edge Mobile Tools to Keep You In The Know

Orbitz sends you free alerts and updates on your Monroe County flight wherever you are in the world. Once you have downloaded the free app for your iPhone, Android, or iPad, you can review or alter any travel plans that you have made or even book a future flight for business or pleasure. If you need to reserve a hotel room when booking your flight, you will find exclusive deals on our mobile site.

Frequent Flyer Program Enrolment

Orbitz finds you the lowest fares, but you can still add your miles to your frequent flyer program to earn miles or points on selected flights to Monroe County. When making your booking, reference your frequent flyer number to receive discounts in the future.

Outstanding Customer Service

Orbitz values your business and wants to ensure that all of your flights are as easy as possible to book. If you have booked a flight to Monroe County but need to cancel it, you may be able to do so online. If you have any questions or need help, the dedicated Orbitz customer service team is always standing by.

Frequently asked questions

Which airlines fly to Monroe County?
There are 15 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 $163 to $862 this last week. The lowest one-way ticket was $105, 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.