$44 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 $44 One Way, $83 Round Trip

$83 return flights and $44 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.

Sun, Jan 17 - Thu, Jan 21
PHL
Philadelphia
MIA
Miami
$83 Roundtrip, found 4 hours ago
$83
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sun, Jan 17 from Philadelphia to Miami, returning Thu, Jan 21, priced at $83 found 4 hours ago
Mon, Nov 2 - Thu, Nov 5
PIE
St. Petersburg
EYW
Key West
$86 Roundtrip, just found
$86
Roundtrip
just found
Select Allegiant Air flight, departing Mon, Nov 2 from St. Petersburg to Key West, returning Thu, Nov 5, priced at $86 just found
Mon, Dec 14 - Thu, Dec 17
MCO
Orlando
EYW
Key West
$102 Roundtrip, found 4 hours ago
$102
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Mon, Dec 14 from Orlando to Key West, returning Thu, Dec 17, priced at $102 found 4 hours ago
Sat, Feb 27 - Wed, Mar 3
TPA
Tampa
EYW
Key West
$102 Roundtrip, found 6 hours ago
$102
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Sat, Feb 27 from Tampa to Key West, returning Wed, Mar 3, priced at $102 found 6 hours ago
Wed, Nov 4 - Fri, Nov 6
MCO
Orlando
MIA
Miami
$107 Roundtrip, found 4 days ago
$107
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Wed, Nov 4 from Orlando to Miami, returning Fri, Nov 6, priced at $107 found 4 days ago
Sat, Nov 14 - Thu, Nov 19
MCO
Orlando
MIA
Miami
$117 Roundtrip, found 4 days ago
$117
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, Nov 14 from Orlando to Miami, returning Thu, Nov 19, priced at $117 found 4 days ago
Wed, Nov 18 - Thu, Nov 19
MCO
Orlando
MIA
Miami
$146 Roundtrip, found 2 hours ago
$146
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Wed, Nov 18 from Orlando to Miami, returning Thu, Nov 19, priced at $146 found 2 hours ago
Tue, Dec 1 - Tue, Dec 8
ORD
Chicago
MIA
Miami
$177 Roundtrip, found 2 hours ago
$177
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Tue, Dec 1 from Chicago to Miami, returning Tue, Dec 8, priced at $177 found 2 hours ago
Mon, Dec 7 - Thu, Dec 10
SFO
San Francisco
MIA
Miami
$248 Roundtrip, just found
$248
Roundtrip
just found
Select Southwest Airlines flight, departing Mon, Dec 7 from San Francisco to Miami, returning Thu, Dec 10, priced at $248 just found
Tue, Dec 8 - Wed, Dec 16
ORD
Chicago
EYW
Key West
$293 Roundtrip, just found
$293
Roundtrip
just found
Select American Airlines flight, departing Tue, Dec 8 from Chicago to Key West, returning Wed, Dec 16, priced at $293 just found
Tue, May 4 - Tue, May 18
SFO
San Francisco
EYW
Key West
$341 Roundtrip, found 1 day ago
$341
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, May 4 from San Francisco to Key West, returning Tue, May 18, priced at $341 found 1 day ago
Tue, Nov 10 - Fri, Nov 20
ORD
Chicago
AVT
Aventura
$342 Roundtrip, found 6 days ago
$342
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Tue, Nov 10 from Chicago to Aventura, returning Fri, Nov 20, priced at $342 found 6 days ago

Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
PIEKey WestOctober 25 to October 31$86
ATLMiamiOctober 23 to October 24$124
PHLMiamiOctober 24 to October 28$135
CLTMiamiOctober 25 to October 29$196
TPAMiamiOctober 25 to October 29$243
DTWMiamiOctober 25 to October 27$349
EWRMiamiOctober 25 to October 31$349
EWRMiamiOctober 25 to October 31$349
LGAKey WestOctober 23 to October 29$484
EWRKey WestOctober 24 to October 28$508
DTWKey WestOctober 23 to October 27$556
BOSMiamiOctober 25 to November 1$577
BOSKey WestOctober 23 to October 26$624
PHLKey WestOctober 23 to October 24$626
ATLKey WestOctober 25 to October 28$938
*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
$234 nightly
The price is $263 total per night from Oct 21 to Oct 22
$263 total
Oct 21 - Oct 22
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
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$265 nightly
The price is $298 total per night from Oct 20 to Oct 21
$298 total
Oct 20 - Oct 21
Total with taxes and fees
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 ...
8.8/10 Excellent! (1,800 reviews)
"All perfect!! Nice place"

Reviewed on Oct 18, 2026

Opens in a new windowMargaritaville Beach House Key West
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 Oct 25 to Oct 26
$197 total
Oct 25 - Oct 26
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! (2,737 reviews)
"It was my first time to Key West with friends and we didnt know where to stay but we are glad we choose the Blue Flamingo. We had a late arrival from Miami and checked in about 130am which was quick and easy. Our room was clean, comfy beds, great AC 👌 since we were exhausted from traveling. We stayed ..."

Reviewed on Oct 19, 2026

Opens in a new windowBlue Flamingo Resort Key West
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Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
$200 nightly
The price is $225 total per night from Nov 3 to Nov 4
$225 total
Nov 3 - Nov 4
Total with taxes and fees
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 ...
9/10 Wonderful! (1,884 reviews)
"My boyfriend and I went to this resort as part of his birthday plans and we had a great time. The resort’s theme was nice, music was a vibe (Latin), and everything was very clean. The food truck they have by the pool was a great spot to hit for breakfast and lunch as for convenience (can be a pricey, ..."

Reviewed on Oct 19, 2026

Opens in a new windowHavana Cabana at 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?

Fullsize

Nissan Altima
  • 5 people
  • Unlimited mileage
MIAMI, USA
Nissan Altima

$4

$11 total
found 1 day ago
Fullsize Nissan Altima

Economy

Toyota Yaris 2dr
  • 4 people
  • Unlimited mileage
MIAMI, USA
Toyota Yaris 2dr

$4

$11 total
found 1 day ago
Economy Toyota Yaris 2dr

Midsize

Toyota Corolla
  • 5 people
  • Unlimited mileage
MIAMI, USA
Toyota Corolla

$4

$11 total
found 1 day ago
Midsize Toyota Corolla

Compact

Nissan Versa
  • 5 people
  • Unlimited mileage
MIAMI, USA
Nissan Versa

$4

$11 total
found 1 day ago
Compact Nissan Versa

Monroe County

Save more on flights to Monroe County while making top-quality travel arrangements. At Orbitz we provide access to low cost flights, hotel lodgings and other discounts, along with superior customer service and an unbeatable satisfaction guarantee.

Compare And Book Discount Flights to Monroe County

Now it is easier than ever to find a discount Monroe County flight. Orbitz users can compare airfares for both international and domestic flights and can quickly determine the best hotels and car rental companies to use. You may also check out hotel and other reviews along with a number of travel tips, making your visit to an unfamiliar destination enjoyable and hassle-free.

Use Your Mobile Phone To Secure A Low Cost Flight To Monroe County

We now offer free apps for the most commonly used mobile devices. You can use your mobile phone to share relevant information pertaining to your trips, view images of local lodgings and take advantage of hotel and car rental discounts that may be available only to mobile device users.

Boost Your Frequent Flyer Rewards

You even retain your ability to earn frequent flier points and rewards when purchasing your tickets with Orbitz for Monroe County flights. Enter your frequent flyer information into your Orbitz profile to start earning rewards.

You will find that Orbitz is a very low cost, yet very effective travel planner. Free updates via your mobile phone device will help to keep you and all relevant parties informed of important flight updates. With access to unbeatable sales on all travel essentials, Orbitz makes booking an affordable flight to Monroe County a breeze.

Frequently asked questions

Which airlines fly to Monroe County?
There are 24 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 $83 to $938 this last week. The lowest one-way ticket was $44, coming from Philadelphia (PHL).
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.