$41 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 $41 One Way, $82 Round Trip

$82 return flights and $41 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, Sep 19 - Sat, Sep 26
TPA
Tampa
EYW
Key West
$82 Roundtrip, found 1 hour ago
$82
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Sat, Sep 19 from Tampa to Key West, returning Sat, Sep 26, priced at $82 found 1 hour ago
Wed, Sep 23 - Fri, Sep 25
TPA
Tampa
EYW
Key West
$83 Roundtrip, found 1 hour ago
$83
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Wed, Sep 23 from Tampa to Key West, returning Fri, Sep 25, priced at $83 found 1 hour ago
Wed, Aug 12 - Wed, Aug 19
PIE
St. Petersburg
EYW
Key West
$86 Roundtrip, just found
$86
Roundtrip
just found
Select Allegiant Air flight, departing Wed, Aug 12 from St. Petersburg to Key West, returning Wed, Aug 19, priced at $86 just found
Wed, Sep 23 - Fri, Sep 25
TPA
Tampa
EYW
Key West
$88 Roundtrip, found 1 hour ago
$88
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Wed, Sep 23 from Tampa to Key West, returning Fri, Sep 25, priced at $88 found 1 hour ago
Mon, Aug 31 - Wed, Sep 2
BWI
Baltimore
MIA
Miami
$106 Roundtrip, found 4 hours ago
$106
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Mon, Aug 31 from Baltimore to Miami, returning Wed, Sep 2, priced at $106 found 4 hours ago
Wed, Aug 26 - Wed, Aug 26
TPA
Tampa
MIA
Miami
$146 Roundtrip, found 1 day ago
$146
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Aug 26 from Tampa to Miami, returning Wed, Aug 26, priced at $146 found 1 day ago
Wed, Oct 21 - Fri, Oct 23
TPA
Tampa
MIA
Miami
$149 Roundtrip, found 20 hours ago
$149
Roundtrip
found 20 hours ago
Select American Airlines flight, departing Wed, Oct 21 from Tampa to Miami, returning Fri, Oct 23, priced at $149 found 20 hours ago
Wed, Sep 9 - Sat, Sep 12
EWR
New York
MIA
Miami
$179 Roundtrip, found 2 hours ago
$179
Roundtrip
found 2 hours ago
Select United flight, departing Wed, Sep 9 from New York to Miami, returning Sat, Sep 12, priced at $179 found 2 hours ago
Sat, Sep 5 - Tue, Sep 8
JFK
New York
MIA
Miami
$182 Roundtrip, just found
$182
Roundtrip
just found
Select Delta flight, departing Sat, Sep 5 from New York to Miami, returning Tue, Sep 8, priced at $182 just found
Tue, Oct 6 - Tue, Oct 13
EWR
New York
EYW
Key West
$319 Roundtrip, found 7 hours ago
$319
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Tue, Oct 6 from New York to Key West, returning Tue, Oct 13, priced at $319 found 7 hours ago
Wed, Dec 2 - Sat, Dec 5
JFK
New York
EYW
Key West
$321 Roundtrip, found 1 day ago
$321
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Dec 2 from New York to Key West, returning Sat, Dec 5, priced at $321 found 1 day ago
Thu, Feb 4 - Sun, Feb 7
BWI
Baltimore
EYW
Key West
$329 Roundtrip, found 4 days ago
$329
Roundtrip
found 4 days ago
Select American Airlines flight, departing Thu, Feb 4 from Baltimore to Key West, returning Sun, Feb 7, priced at $329 found 4 days ago
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Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
PIEKey WestAugust 9 to August 12$86
ATLMiamiAugust 7 to August 8$184
CLTMiamiAugust 9 to August 10$209
PHLMiamiAugust 8 to August 13$250
TPAMiamiAugust 9 to August 13$263
DTWMiamiAugust 9 to August 14$288
EWRMiamiAugust 9 to August 13$340
BOSMiamiAugust 8 to August 13$483
EWRKey WestAugust 7 to August 11$505
BWIKey WestAugust 7 to August 10$505
BOSKey WestAugust 7 to August 13$534
PHLKey WestAugust 9 to August 18$558
CLTKey WestAugust 7 to August 9$734
DTWKey WestAugust 7 to August 10$739
ATLKey WestAugust 7 to August 9$753
*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
$210 nightly
The price is $237 total per night from Aug 17 to Aug 18
$237 total
Aug 17 - Aug 18
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
$202 nightly
The price is $227 total per night from Aug 17 to Aug 18
$227 total
Aug 17 - Aug 18
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! (2,394 reviews)
"We loved the ocean view family suite. Beautiful decor, plenty of space and beautiful ocean views from the balconies. It had all the items we needed and really nicely furnished. Hotel staff were very accommodating and friendly throughout our stay. Unfortunately, due to understaffing, pool area became ..."

Reviewed on Jul 31, 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
$202 nightly
The price is $227 total per night from Aug 12 to Aug 13
$227 total
Aug 12 - Aug 13
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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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
$166 nightly
The price is $187 total per night from Aug 30 to Aug 31
$187 total
Aug 30 - Aug 31
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! (2,596 reviews)
"This property has the best hang out and pool area of any resort I have stayed at - 2 great pools, wonderful bar, 2 restaurant options, and great outdoor games space. The hotel staff are very helpful and friendly and the location is great to provide a fun and relaxing vacation or honeymoon while still ..."

Reviewed on Jul 31, 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

Snag some “suite” deals when you add cheap hotel rooms to Monroe County flights at Orbitz. You can score tickets to ballgames, concerts and other activities while planning your low fare flights. For non-stop air tickets or planned layovers, Orbitz is your discount travel resource.

Budget Prices, Luxury Life

Find mobile-only bargains on your home away from home with Orbitz cutting-edge mobile tools. Search domestic and international hotels at Orbitz On the Go. Find free travel planning apps for your iPhone, Android or iPad. You’ll always get our guaranteed low prices on your favorite hotels and flights to Monroe County.

Fun for All

While shopping Orbitz sales on Monroe County flights, remember to throw in some fun. Ticket sales for music, theatre, sports and more can be found on the Activities page. Just tell us what you want to do, and Orbitz will save your seat.

Non-Stop or Stop and Visit

Will you be flying round-trip or one-way? Going directly from Point A to Point B? Maybe you’d like to have dinner with family and friends along the way. Whether you need non-stop flights to {destination.name} or lowest cost layovers on Monroe County flights, you will always find the best air travel prices at Orbitz.

All in One

Now you can custom design the perfect travel package with Orbitz and save more when booking your flights to Monroe County. Do you have a favorite airline, hotel or car rental company? Every page at Orbitz gives you complete freedom to create your travel plans according to your unique wants and needs. Orbitz is designed to meet your discount travel planning needs completely and conveniently.

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 $82 to $753 this last week. The lowest one-way ticket was $41, coming from Tampa (TPA).
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.