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Florida Deal Alert: Escape to Key West, Miami this winter for under $299

Oct. 16, 2021
6 min read
Silhouette Pier Over Sea Against Sky During Sunset
Florida Deal Alert: Escape to Key West, Miami this winter for under $299
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This is an absolutely fantastic time to book your winter escape to Florida. There are great fares to be had from dozens of U.S. cities to Key West so you can leave your cold-weather gear behind, put on your swimsuit and enjoy a cold beverage on the beach.

Our friends at Thrifty Traveler let us know about the great prices you can find for travel to Ernest Hemingway's beloved tropical getaway on American, Delta and United. Many of the Key West fare prices apply in reverse, so if you're in the Keys and you want to see what it's like to actually have to wear long sleeves during the winter, you can enjoy the sale prices, too.

There are also bargains to be found for Miami and Fort Lauderdale, as well, and we've listed a few below.

American and United fares are for Main Cabin seats, which come with a free carry-on and seat assignment. Delta bookings are for Basic Economy.

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Distance sign in the key West's beach (photo by cristianl for Getty Images)

Airlines: American, Delta and United Airlines.
Routes: ATL/AVL/BHM/BOS/CHS/DTW/EWR/JFK/SAT and many others to EYW/MIA/FLL.
Cost: Roundtrip fares under $299 for Main Cabin (American, United) and Basic Economy (Delta).
Dates: November-September 2022 (includes Thanksgiving).
Pay with: The Platinum Card® from American Express for 5x on airfare booked directly with the airline or through American Express Travel (on up to $500,000 on these purchases per calendar year), the Citi Prestige® Card for 5x on airfare, the Citi Premier® Card or Chase Sapphire Reserve for 3x on air travel, the American Express® Gold Card for 3x on airfare when booked directly with the airline or through Amex Travel, or the Chase Sapphire Preferred Card for 2x on travel.

The information for the Citi Prestige Card has been collected independently by The Points Guy. The card details on this page have not been reviewed or provided by the card issuer.

Some examples of the round-trip fares to Key West (EYW) that are part of this deal are:

  • New York City (JFK) for as low as $175, nonstop
  • Atlanta (ATL) for as low as $197, nonstop
  • Detroit (DTW) for as low as $235
  • Dallas (DFW) for as low as $253
  • Kansas City (MCI) for as low as $235
  • Minneapolis (MSP) for as low as $257

Boston to Key West has lots of availability from November to March for under $250, but mid-November had several itineraries for just $169 round-trip on American. This is for a Main Cabin seat, which has the free carry-on and seat assignment, as mentioned above.

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(screenshot courtesy of Google Flights)

New York snowbirds can head south all winter for very reasonable rates, such as this $175 fare we were alerted to by our pals at Scott's Cheap Flights, from JFK to Key West International (EYW).

(screenshot courtesy of Google Flights)

Here's an excellent deal from Little Rock to the Keys for under $200. We didn't see as much availability at this price point for this route, so Arkansas travelers thinking of heading south should jump on this now. This is for United's Economy tier, so you get free seat selection and a carry-on, plus you can change your flight at no charge, but you will have to pay any difference in the ticket price.

(screenshot courtesy of Google Flights)

The coldest month of the year in Milwaukee is January, with an average overnight temperature of an absolutely arctic 13.4 degrees Fahrenheit. Booking a flight to Key West at any price sounds appealing when it's that cold, but when you can get a round-trip Main Cabin ticket for $236? That's a no-brainer.

(screenshot courtesy of Google Flights)

Houston to the Keys is just $209 right now via American. We found the best availability for a long weekend in December and January.

(screenshot courtesy of Google Flights)

We also found killer deals for flights to other popular Florida destinations. For example, Houston to Fort Lauderdale on American in February can be booked for just $127, nonstop.

(screenshot courtesy of Google Flights)

Detroit to Miami in February is even cheaper. You can book a nonstop ticket for only $117 on American right now.

(screenshot courtesy of Google Flights)

Nashville to Miami is also a trip to consider as prices are much lower than usual. February seems to be the month with the lowest prices. We found this rate for $147, nonstop.

(screenshot courtesy of Google Flights)

Let's end go back to New England for our final heads up, about a fare price that is simply rock bottom -- Boston to Miami nonstop in January for just $97 round-trip! That certainly sounds like a wonderful belated Christmas present.

(screenshot courtesy of Google Flights)

How to book your flights

The easiest way to do it is if you’re a Thrifty Traveler or Scott's Cheap Flights premium subscriber. You can also simply use Google Flights, plug in your destination city and start searching for dates that fit your travel schedule.

Maximize your purchase

Don’t forget to use a card that earns additional points on airfare purchases, such as The Platinum Card from American Express (5x on flights booked directly with airlines or Amex Travel, on up to $500,000 on these purchases per calendar year), Chase Sapphire Reserve (3x on air travel), American Express Gold Card (3x on flights booked directly with airlines or Amex Travel), Citi Premier Card (3x on air travel) or the Chase Sapphire Preferred Card (2x on travel purchases). Check out this guide for more on maximizing airfare purchases.

Featured image by Getty Images/EyeEm
Editorial disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airline or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.