$58 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 $58 One Way, $104 Round Trip

$104 return flights and $58 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, Aug 25 - Wed, Aug 26
BWI
Baltimore
MIA
Miami
$113 Roundtrip, found 7 hours ago
$113
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Tue, Aug 25 from Baltimore to Miami, returning Wed, Aug 26, priced at $113 found 7 hours ago
Wed, Aug 12 - Wed, Aug 19
DFW
Dallas
MIA
Miami
$148 Roundtrip, found 2 hours ago
$148
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Wed, Aug 12 from Dallas to Miami, returning Wed, Aug 19, priced at $148 found 2 hours ago
Mon, Oct 5 - Thu, Oct 8
SFO
San Francisco
MIA
Miami
$240 Roundtrip, just found
$240
Roundtrip
just found
Select Frontier Airlines flight, departing Mon, Oct 5 from San Francisco to Miami, returning Thu, Oct 8, priced at $240 just found
Mon, Oct 19 - Thu, Oct 22
DAL
Dallas
MIA
Miami
$291 Roundtrip, found 22 hours ago
$291
Roundtrip
found 22 hours ago
Select Southwest Airlines flight, departing Mon, Oct 19 from Dallas to Miami, returning Thu, Oct 22, priced at $291 found 22 hours ago
Fri, Sep 11 - Tue, Sep 15
BWI
Baltimore
EYW
Key West
$319 Roundtrip, found 22 hours ago
$319
Roundtrip
found 22 hours ago
Select American Airlines flight, departing Fri, Sep 11 from Baltimore to Key West, returning Tue, Sep 15, priced at $319 found 22 hours ago
Sat, Nov 14 - Thu, Nov 19
SFO
San Francisco
EYW
Key West
$369 Roundtrip, found 22 hours ago
$369
Roundtrip
found 22 hours ago
Select American Airlines flight, departing Sat, Nov 14 from San Francisco to Key West, returning Thu, Nov 19, priced at $369 found 22 hours ago
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Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
PIEKey WestJuly 26 to July 30$104
ATLMiamiJuly 25 to July 28$238
DTWMiamiJuly 25 to July 28$313
CLTMiamiJuly 26 to July 31$314
PHLMiamiJuly 25 to July 28$328
TPAMiamiJuly 24 to July 28$328
JFKMiamiJuly 24 to July 25$394
EWRMiamiJuly 24 to July 25$414
LGAKey WestJuly 24 to July 28$467
EWRKey WestJuly 24 to July 28$468
DTWKey WestJuly 25 to July 28$473
PHLKey WestJuly 25 to July 27$562
BOSMiamiJuly 26 to September 16$596
CLTKey WestJuly 24 to July 27$617
BOSKey WestJuly 26 to July 30$741
*Prices include taxes and fees

Find The Perfect Hotel For After Your Flight

Score Epic Monroe County Accommodation Deals

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. ...
Opens in a new windowBeachside Resort & Residences
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 18 to Aug 19
$237 total
Aug 18 - Aug 19
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! (3,456 reviews)
"We could not use the beach during the whole weekend due to seaweed, the beach was never cleaned during my stay"

Reviewed on Jul 22, 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
$155 nightly
The price is $175 total per night from Aug 16 to Aug 17
$175 total
Aug 16 - Aug 17
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 ...
Opens in a new windowHilton Garden Inn Key West / The Keys Collection
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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
$226 nightly
The price is $254 total per night from Aug 3 to Aug 4
$254 total
Aug 3 - Aug 4
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
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

End your search for discount fares on flights to Monroe County. Orbitz has all the best prices on Monroe County flights. With Orbitz, you can expect:

Cheap Deals on Flights to Monroe County

We offer big discounts and last-minute savings on Monroe County flights. We make it easy for you to research, plan, and book your flight to Monroe County — all while offering great low fares. With guaranteed low prices and cutting-edge mobile tools, the perfect trip begins on Orbitz.

Travel Convenience on the Go

Get alerts, updates, or book your Monroe County flight or other flights wherever you are. Download our free apps for iPhone, Android, and iPad or visit our mobile site at m.orbitz.com to conveniently review or change your air travel plans. We can also send free alerts about your Monroe County flight to your email or mobile phone, so you get advance warning about potential disruptions and flight delays. Need to book a hotel with your Monroe County flight? Access exclusive, mobile-only deals via our mobile site and free apps – even on the same day.

Great Customer Care

We want to make your travel booking experience smooth and easy, from planning and researching Monroe County flights to the actual booking. If you want to cancel your flight to Monroe County, many tickets can be conveniently cancelled online. Contact our Customer Service to make changes to your air ticket.

Miles or Points Toward Frequent Flyer Programs

Much like booking with an airline directly, you can earn frequent flyer miles or points on qualified flights to Monroe County with Orbitz. When completing your booking, just fill in your frequent flyer number for the airline you are flying with or for one of its available partner airlines.

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 $104 to $741 this last week. The lowest one-way ticket was $58, coming from Baltimore (BWI).
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.