Flights To Monroe County - Cheap Flights Starting at CA $243

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Jet to one of Monroe County's top cities

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

Key West

Flights
Key West

How Much Does it Cost To Fly To Monroe County?

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Fri, Mar 12 - Sun, Mar 21
YYZ
Pearson Intl.
MIA
Miami Intl.
CA $412 Roundtrip, just found
CA $412
Roundtrip
just found
Select Air Transat flight, departing Fri, Mar 12 from Pearson Intl. to Miami Intl., returning Sun, Mar 21, priced at CA $412 just found
Mon, Oct 26 - Thu, Oct 29
YYZ
Pearson Intl.
MIA
Miami Intl.
CA $454 Roundtrip, found 8 hours ago
CA $454
Roundtrip
found 8 hours ago
Select Air Transat flight, departing Mon, Oct 26 from Pearson Intl. to Miami Intl., returning Thu, Oct 29, priced at CA $454 found 8 hours ago
Mon, Nov 23 - Mon, Nov 30
YOW
Macdonald-Cartier Intl.
MIA
Miami Intl.
CA $481 Roundtrip, just found
CA $481
Roundtrip
just found
Select Porter Airlines flight, departing Mon, Nov 23 from Macdonald-Cartier Intl. to Miami Intl., returning Mon, Nov 30, priced at CA $481 just found
Mon, Nov 23 - Fri, Nov 27
YUL
Pierre Elliott Trudeau Intl.
MIA
Miami Intl.
CA $487 Roundtrip, found 4 hours ago
CA $487
Roundtrip
found 4 hours ago
Select Porter Airlines flight, departing Mon, Nov 23 from Pierre Elliott Trudeau Intl. to Miami Intl., returning Fri, Nov 27, priced at CA $487 found 4 hours ago
Wed, Mar 3 - Wed, Mar 10
YYZ
Pearson Intl.
MIA
Miami Intl.
CA $501 Roundtrip, found 11 hours ago
CA $501
Roundtrip
found 11 hours ago
Select Air Transat flight, departing Wed, Mar 3 from Pearson Intl. to Miami Intl., returning Wed, Mar 10, priced at CA $501 found 11 hours ago
Wed, Mar 3 - Sat, Mar 13
YUL
Pierre Elliott Trudeau Intl.
MIA
Miami Intl.
CA $503 Roundtrip, found 23 hours ago
CA $503
Roundtrip
found 23 hours ago
Select Air Transat flight, departing Wed, Mar 3 from Pierre Elliott Trudeau Intl. to Miami Intl., returning Sat, Mar 13, priced at CA $503 found 23 hours ago
Fri, Feb 26 - Sat, Mar 6
YYZ
Pearson Intl.
MIA
Miami Intl.
CA $524 Roundtrip, found 3 hours ago
CA $524
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Fri, Feb 26 from Pearson Intl. to Miami Intl., returning Sat, Mar 6, priced at CA $524 found 3 hours ago
Mon, Oct 26 - Thu, Nov 12
YUL
Pierre Elliott Trudeau Intl.
MIA
Miami Intl.
CA $524 Roundtrip, found 20 hours ago
CA $524
Roundtrip
found 20 hours ago
Select Air Transat flight, departing Mon, Oct 26 from Pierre Elliott Trudeau Intl. to Miami Intl., returning Thu, Nov 12, priced at CA $524 found 20 hours ago
Sun, Jan 10 - Fri, Jan 15
YYZ
Pearson Intl.
MIA
Miami Intl.
CA $533 Roundtrip, just found
CA $533
Roundtrip
just found
Select American Airlines flight, departing Sun, Jan 10 from Pearson Intl. to Miami Intl., returning Fri, Jan 15, priced at CA $533 just found
OriginDestinationTravel datesFlights from*
TPAKey WestJanuary 10 to January 13CA $145
PHLMiamiNovember 11 to November 13CA $182
CLTMiamiNovember 6 to November 9CA $211
EWRMiamiNovember 11 to November 16CA $224
EWRMiamiNovember 11 to November 16CA $224
DTWMiamiNovember 7 to November 12CA $249
TPAMiamiNovember 5 to November 9CA $281
BOSMiamiJanuary 5 to January 12CA $283
ORDMiamiNovember 7 to November 12CA $295
JFKKey WestDecember 12 to December 17CA $477
BOSKey WestDecember 10 to December 17CA $537
BWIKey WestNovember 6 to November 11CA $698
EWRKey WestNovember 26 to December 8CA $760
DTWKey WestNovember 28 to December 5CA $835
PHLKey WestNovember 12 to November 14CA $1,114
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
ATLMiamiOctober 16 to October 17CA $176
CLTMiamiOctober 16 to October 19CA $240
BWIMiamiOctober 17 to October 21CA $260
TPAKey WestOctober 17 to October 19CA $276
DTWMiamiOctober 17 to October 26CA $495
ORDMiamiOctober 18 to October 25CA $609
JFKMiamiOctober 18 to October 21CA $717
PHLDowntown MiamiOctober 18 to October 23CA $769
EWRMiamiOctober 16 to October 18CA $782
BOSKey WestOctober 16 to October 18CA $831
BOSDowntown MiamiOctober 17 to October 24CA $1,009
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Cavalier Hotel South Beach
3.5-star property

Cavalier Hotel South Beach

Dec 31 - Jan 4

4 night stay

Hamilton (YHM) to Miami (MIA)

Air Canada • Non-stop roundtrip • Coach
Save 100% on your flight
Price was CA $2,917, price is now CA $1,753 per person
CA $1,753
per person
found 1 day ago
The Retreat Collection at 1 Hotel & Homes South Beach
5.0-star property

The Retreat Collection at 1 Hotel & Homes South Beach

Dec 29 - Jan 2

4 night stay

Toronto (YTO) to Miami (MIA)

Air Canada • Non-stop roundtrip • Coach
Price was CA $47,673, price is now CA $24,827 per person
CA $24,827
per person
found 1 day ago
President Hotel Villa
3.5-star property

President Hotel Villa

Dec 29 - Jan 4

6 night stay

Toronto (YTO) to Miami (MIA)

Air Canada • Non-stop roundtrip • Coach
Save 100% on your flight
Price was CA $3,177, price is now CA $1,890 per person
CA $1,890
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Hamilton to Monroe County
View all trips

Travelers ❤️ These Monroe County 🏨

Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
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 in our reviews. Popular attractions Florida Keys Brewing Co. and Lorelei Restaurant & Cabana Bar are located nearby.
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
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 in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
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
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 in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
Opens in a new windowBlue Flamingo Resort Key West
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
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 staff in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
9/10 Wonderful! (1,880 reviews)
"This was our second stay here. We love the low key vibe. The staff is always pleasant to deal with. The rooms are nice and the pool was well maintained. The food was great. All around great experience will be back again and again."

Reviewed on Oct 12, 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.

Frequently asked questions

How much is the cheapest flight to Monroe County?
A roundtrip flight to Monroe County cost as little as CA $145 in the last seven days. Once you've chosen your travel dates, we'll help you grab an amazing deal. This price was available on Travelocity for flights to Monroe County departing within the next year. Prices and availability are subject to change. Additional terms apply.
What is the cheapest month to fly to Monroe County?
Be sure to leave March clear in your calendar, because it's the cheapest month to head to Monroe County. That's based on Travelocity's direct flight demand from January to December last year. With more money in your wallet, you can go on a shopping binge, go to a concert or whatever else you like!
How can I check my flight status to Monroe County?
There are a few ways you can check the status of your flight. You'll find all the necessary info in our "Trips" portal, which is located at the top right of our homepage. Sign in or create a new account in seconds — you can then view and make changes to your bookings whenever you want to. For those on the move, the Travelocity app can also help you check the status of your flight to Monroe County, as well as share details with any members of your family flying with you.
How do I find the best deals on flights to Monroe County?
It pays to book in advance, and if you can, avoid traveling during high season. Another smart way to save is by clicking the "Flexible dates" box at the top of the page after searching for your flights. This will reveal ticket prices for surrounding days. In the last seven days, the lowest price for a roundtrip flight to Monroe County was CA $145. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Monroe County with Travelocity?
Search for cheap flights to Monroe County with Travelocity and begin arranging your next getaway. With round-the-clock customer support during every stage of your trip and a Price Match Guarantee, we take the worry out of reserving cheap family flights, hotels, experiences and more. Bag a fantastic deal today and brace yourself for an epic adventure.
What are the most popular flight routes to Monroe County?
Browse through these major flight routes to Monroe County and start planning your next big adventure:

  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Key West Intl. Airport (EYW) - 849 flights a month.
  • Miami, FL (MIA-Miami Intl.) to Key West Intl. Airport (EYW) - 637 flights a month.
  • Charlotte, NC (CLT-Charlotte-Douglas Intl.) to Key West Intl. Airport (EYW) - 442 flights a month.

How much is a flight to Monroe County on average?
Travelers have found roundtrip flights to Monroe County for between CA $145 and CA $1,114 with Travelocity in the last seven days. Whether you're planning to fly economy or business class, we'll help you get a fabulous deal. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.