TLH - SXM

$757 Find Cheap Flights from Tallahassee to Simpson Bay - Compare and Save

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Tallahassee to Simpson Bay departing on 8/17. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$757
American Airlines
Mon 8/17Mon 8/24
TLH - SXM • 1 stop
Nonstop flights
Not available
There are currently no direct flights between Tallahassee and Simpson Bay. You'll need at least 1 connection.
Insights
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Insights
Top layover airports
Cheapest • Avg $773 (round-trip)
Shortest trip • 6h 50m (one-way)
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We hope you love your trip to Simpson Bay!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Tallahassee to Simpson Bay (TLH-SXM)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Tallahassee to Simpson Bay that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Tallahassee to Simpson Bay

Mon, Aug 17 - Mon, Aug 24
American Airlines Logo
9:51 am - 3:39 pm
TLH
-
SXM
5h 48m
1 stop
American Airlines Logo
2:22 pm - 11:59 pm
SXM
-
TLH
9h 37m
1 stop
$757American Airlines
Mon, Aug 17 - Mon, Aug 24
American Airlines Logo
6:25 pm - 3:39 pm
TLH
-
SXM
21h 14m
2 stops
American Airlines Logo
4:39 pm - 3:33 pm
SXM
-
TLH
22h 54m
2 stops
$762American Airlines
Booking Insights

KAYAK's insights & trends for Tallahassee to Simpson Bay flights

Get data-powered insights and trends into flights from Tallahassee to Simpson Bay to help you find the cheapest flights, the best time to fly and much more.

What is the most popular layover airport when flying from Tallahassee to Simpson Bay?

Percentage of 1-stop round-trip flights from Tallahassee to Simpson Bay chosen by KAYAK users via each layover airport in the last 12 months (only includes trips with the same layover airport on both legs).

Miami (MIA) is the top choice – 73% of KAYAK users who clicked on 1-stop flights from Tallahassee to Simpson Bay picked an itinerary connecting there.

What is the cheapest layover airport when flying from Tallahassee to Simpson Bay?

Average round-trip price for 1-stop flights from Tallahassee to Simpson Bay clicked by KAYAK users in the last 12 months (only includes trips with the same layover airport on both legs).

Flights via Miami (MIA) offer the most affordable fares, with an average round-trip price of $773.

Which layover airport offers the shortest total travel time from Tallahassee to Simpson Bay?

Shortest average total travel time for 1-stop one-way flights from Tallahassee to Simpson Bay via different layover airports, based on KAYAK user data from the last 12 months.

Consider flying via Miami (MIA) for the shortest journey. The average one-way travel time for flights connecting there is 6h 50m.

Which layover airport has the quickest connection when flying from Tallahassee to Simpson Bay?

Average layover duration at different layover airports for 1-stop one-way flights from Tallahassee to Simpson Bay, based on KAYAK user data from the last 12 months.

If you prefer a quick connection, Charlotte (CLT) often has the shortest layovers from Tallahassee to Simpson Bay, with an average of 1h 35m.

Good to know

Cheapest flight

$757
Flight from Tallahassee to Simpson Bay

When to book flights from Tallahassee to Simpson Bay

Are your dates flexible? Find out the best times to travel from Tallahassee to Simpson Bay based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Tallahassee to Simpson Bay

  • What is the cheapest flight from Tallahassee to Simpson Bay?

    In the last 5 days, the lowest price for a flight from Tallahassee to Simpson Bay was $757 for a round-trip ticket.

  • Do I need a passport to fly between Tallahassee and Simpson Bay?

    Yes, you'll most likely have to show a valid passport before boarding the plane in Tallahassee and on arrival in Simpson Bay.

  • Which aircraft models fly most regularly from Tallahassee to Simpson Bay?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Tallahassee to Simpson Bay?

    oneworld is the only airline alliance operating flights between Tallahassee and Simpson Bay.

  • How does KAYAK find such low prices on flights from Tallahassee to Simpson Bay?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Tallahassee to Simpson Bay.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Tallahassee to Simpson Bay?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Simpson Bay from Tallahassee is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Tallahassee to Simpson Bay?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Simpson Bay with an airline and back to Tallahassee with another airline. Booking your flights between Tallahassee and SXM can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Tallahassee to Simpson Bay?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Simpson Bay from Tallahassee up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Tallahassee to Simpson Bay

 
See real verified KAYAK customer reviews for airlines flying from Tallahassee to Simpson Bay. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Tallahassee to Simpson Bay? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.1
American AirlinesOverall score based on 11826 reviews
6.4Food
7.5Boarding
6.8Entertainment
7.2Comfort
7.9Crew
Airline reviews

- flight was delayed several hours due to weather (understandable) - flight delayed further and we were told by attendants "we are not sure where the pilots are but they are on their way" as we have to find different pilots for the flight - announcements over the PA were somewhat unprofessional by the attendants, seems they need more training and were not reading off the script. They showed their young age and immaturity in their communications with the passengers. They were not clear and lacked professional communication language. - going from a hub to hub we were also parked at the tarmac at ohare for an additional hour and kept being told "few more minutes". Please just let the passengers know the real wait time instead of hiding the truth. We understand there is traffic and weather delays, but we just want transparency. There are several logistics of our lives that revolve around what the attendants and pilots are sharing with us but they are not being transparant.

4.0 OkaySyeda, Jul 2026
MIA - ORD
Read more American Airlines reviews

- flight was delayed several hours due to weather (understandable) - flight delayed further and we were told by attendants "we are not sure where the pilots are but they are on their way" as we have to find different pilots for the flight - announcements over the PA were somewhat unprofessional by the attendants, seems they need more training and were not reading off the script. They showed their young age and immaturity in their communications with the passengers. They were not clear and lacked professional communication language. - going from a hub to hub we were also parked at the tarmac at ohare for an additional hour and kept being told "few more minutes". Please just let the passengers know the real wait time instead of hiding the truth. We understand there is traffic and weather delays, but we just want transparency. There are several logistics of our lives that revolve around what the attendants and pilots are sharing with us but they are not being transparant.

Not great. I understand delays happen due to weather and crew issues, but it was unacceptable that no agents were available at the counters inside the airport for customer service or help getting on a standby list. The app was not helpful either. I stood in line for an hour waiting for someone to show up at the gate to help me get on a standby flight. Customer care does not seem to be a priority.

As I said I never took the flight back from due to earlier delayed that prevented from taking the second trip back and nobody helped me to rebook from kayak

It was awful. My first flight was delayed and as a consequence I lost my second flight to Greensboro. I did not know what to do so I rebook myself a flight to Charlotte . It was very inconvenient I not to have anybody form corporate assisting me either from PwC or from kayak . It is a very disappointing experience that American did not wait 1 minute or told me to rebook before making the first flight

Would have been good to have the live TV outside of the continental United States as AA was promoting they are sponsors of the Fifa World Cup only for the live coverage to end.

Terrible check in experience in Miami airport by a so-called supervisor. Food came and they were picking up trash within 5 mins. Did not get fed again for about 6 hours. No chance to buy anything on board, horrible experience. Flight attendants have no control over passengers dropping off bags closer to the exit, not close to their seat.

American Airlines changed are gate no fewer than four times. Walking back and forth from one concourse to another was exhausting, especially after all the flight delays.

I cancelled this flight 2 days before departure but I followed your texts and emails and IF you were correct this flight turned into a nightmare.

Baggage claim took too long and priority bags were not delivered first.

I left my wallet on flight 2225, no one has reached out to me yet, I field out the form online. Please give me a call Please.

Everything you need to know for your flight from Tallahassee to Simpson Bay

Information on your arrival and departure airports