Published February 18, 2025 by

Cheap Flights: Houston to/from Fort Myers, Key West, Cleveland, Milwaukee, Richmond, Santa Fe, or West Palm Beach $159-$168 r/t [March-May] – American Airlines

[02/17/2025 @ 09:26 PM CT] Deal time-stamp.
[2025-02-19 07:47:00] Deal expired or removed. If it goes back online we will send out another notification.

Deals are usually valid 24 to 72 hours after posting, but can expire at any time (see time-stamp).

This website contains cookies and links to companies that may compensate this site when you click on their links or ads. To view our ad disclosure and privacy policy, visit this page (link).

To book: Use our updated link list.
Or book with these sites: Priceline, Skyscanner, Expedia, Travelocity, Tripadvisor, Orbitz, CheapTickets, Kayak.

American Airlines has round-trip flights from Houston (IAH/HOU) to Fort Myers, Key West, Cleveland, Milwaukee, Richmond, Santa Fe, or West Palm Beach (RSW, EYW, CLE, MKE, RIC, SAF, PBI) for $159-$168 with a connection. Flights March to May. Most discounted are on departures on Tuesday, Wednesday, and Saturday. Extended weekends available. Origin/Destination reversible.

  • Key West and Santa Fe departures are midweek Tue, Wed, only.

A Carry-on bag and also a personal item is allowed for free on American. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.

If you use the Citi® / AAdvantage® Platinum Select® World Elite Mastercard® with AA flights, you get: a 25% inflight food and beverage discount, a $125 AA flight discount after you spend $20,000 or more in purchases during your card year, and your first checked bag is free on domestic American Airlines flights for you and up to four companions traveling on the same reservation.

You can usually save more money by booking your flight+hotel together as a package instead of separately.

Do a search on Tripadvisor to find guides, tours, restaurants, attractions, and cool things to do. It’s a good resource to use for planning your day-to-day itinerary while on vacation.

We post new flight deals often! You can check out our other deals by returning to the Front Page of our website: escapehouston.com (linked).

Here are some other offers that we think are worth mentioning. List updated 12/04/2025.

We now track coupon codes, discount codes, gift card discounts, and credit card offers that have a better value than their historical averages.

Want a notification sent straight to your phone when any new deals are found? Join our Telegram channel and never miss another deal.

Our website wouldn’t be possible without the direct financial support from our Patreons. If you like the work that we do, then consider becoming a Patreon supporter. We send our supporters an additional daily recap of every fare below the 6-month moving average.

We don’t charge a subscription fee. All our deal notifications are available for FREE via Instagram, Bluesky, Mastodon, Facebook, Twitter, Telegram, our Webpage, and our E-mail list. If you are paying someone a subscription fee for this content, you are being ripped off.

Use the example date links on our website to pull up the fare.

  • Houston to Key West - Extended Weekend Dates: (Expedia) Mar 29 - Apr 01 / Other dates: There may be more dates available than the ones we list here, use the "flexible date" button on Expedia to find similar fares.
 

When you are ready to book your flight or hotel, please use the links on our site to begin your booking process so we receive credit for the referral.

  • Tips: Use Tripadvisor to create a Hotel “short list”. First, plug in your dates and destination. Then select “Sort by Traveler Ranked”. Finally, select the “Traveler Ranking” filter to show “only 4* and up”. Use this resulting “short list” of hotels to find the cheapest one with a high ranking.
  • Tips: Hotel rates for Weekend dates are usually higher than the rates for Sunday through Thursday. Tripadvisor has a color-coded date calendar, red when the average hotel price for that day is more expensive, green for less expensive. You can use this to get an overview of what dates in the month are at a discount.
  • Tips: Different booking websites will often have differing routes, prices, and availability. Before you finalize your purchase, do a quick check on BookingBuddy, Skyscanner, and Kayak to see if any other site or airline is offering a better deal.

Our Affiliate Links:

This site receives referral credit when you use links on our page to open our affiliate’s page. By using our affiliate links when you begin your airfare or hotel search, you are supporting this site. Thanks.

Flights departing from a different city (our other websites):

Other Useful Links:

  • [Budget Travel] – list all the posts that deal with Budget Travel (filter out all the airfare posts)

Ren P. Artemio

Ren P. Artemio

Ren is the Chief Director of Nap Times at Escape Houston, Escape ATX, Cheap DFW, and Escape Flights. He really likes researching airfare and the travel industry, especially when it means getting a cheap flight to anywhere (he's not picky).

Airfare Deals American Airlines Fort Myers Oneworld