$99 Find Cheap Flights from Hartford to Florida Keys

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Hartford to Florida Keys departing on 5/15. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Florida Keys

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Hartford to Florida Keys.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Hartford to Florida Keys.
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Hartford to Florida Keys

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Miami
Miami1 stop$211
Key West
Key West1 stop$159
Miami
Miami1 stop$211
Key West
Key West1 stop$159

Book Cheap Hartford to Florida Keys Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Hartford to Florida Keys 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 Hartford to Florida Keys

Mon, Aug 24 - Fri, Aug 28
Breeze Airways Logo
7:25 am - 12:31 pm
BDL
-
EYW
5h 06m
1 stop
Breeze Airways Logo
1:11 pm - 5:55 pm
EYW
-
BDL
4h 44m
1 stop
$159Breeze Airways
Wed, Jun 3 - Tue, Jun 9
Breeze Airways Logo
6:00 am - 11:06 am
BDL
-
EYW
5h 06m
1 stop
Breeze Airways Logo
1:14 pm - 4:30 pm
EYW
-
BDL
27h 16m
1 stop
$176Breeze Airways
Mon, May 25 - Tue, Jun 2
Breeze Airways Logo
7:25 am - 12:31 pm
BDL
-
EYW
5h 06m
1 stop
Breeze Airways Logo
1:14 pm - 4:30 pm
EYW
-
BDL
27h 16m
1 stop
$179Breeze Airways
Mon, May 25 - Tue, Jun 2
Breeze Airways Logo
7:25 am - 12:31 pm
BDL
-
EYW
5h 06m
1 stop
Breeze Airways Logo
1:14 pm - 4:30 pm
EYW
-
BDL
27h 16m
1 stop
$199Breeze Airways
Wed, May 27 - Tue, Jun 2
Breeze Airways Logo
6:00 am - 11:06 am
BDL
-
EYW
5h 06m
1 stop
Breeze Airways Logo
1:14 pm - 4:30 pm
EYW
-
BDL
27h 16m
1 stop
$205Breeze Airways
Sat, May 23 - Tue, May 26
Frontier Logo
1:48 pm - 12:35 am
BDL
-
MIA
10h 47m
1 stop
Frontier Logo
2:50 pm - 12:44 pm
MIA
-
BDL
21h 54m
1 stop
$211Frontier
Sat, May 30 - Tue, Jun 2
Multiple Airlines Logo
7:43 pm - 11:25 am
BDL
-
EYW
15h 42m
1 stop
Multiple Airlines Logo
1:14 pm - 4:30 pm
EYW
-
BDL
27h 16m
1 stop
$214Multiple Airlines
Tue, Jun 16 - Tue, Jun 23
Frontier Logo
2:10 pm - 10:21 am
BDL
-
MIA
20h 11m
1 stop
Frontier Logo
9:33 pm - 1:15 pm
MIA
-
BDL
15h 42m
1 stop
$216Frontier
Wed, May 27 - Wed, Jun 3
American Airlines Logo
5:45 am - 8:57 am
BDL
-
MIA
3h 12mnonstop
American Airlines Logo
8:47 pm - 11:59 pm
MIA
-
BDL
3h 12mnonstop
$217American Airlines
Sat, May 30 - Sat, Jun 6
American Airlines Logo
5:00 am - 8:12 am
BDL
-
MIA
3h 12mnonstop
American Airlines Logo
8:47 pm - 11:58 pm
MIA
-
BDL
3h 11mnonstop
$218American Airlines
Booking Insights

KAYAK's insights & trends for Hartford to Florida Keys flights

Get data-powered insights and trends into flights from Hartford to Florida Keys to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest time of day to fly to Florida Keys?

The average price for all round-trip flights from Hartford to Florida Keys depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Florida Keys is generally at night, when round-trip flights cost $158 on average. Morning departures are around 53% more expensive than evening flights, on average. The most expensive time of day to fly to Florida Keys is generally in the morning, which is peak travel time and where the average cost of a ticket is $515.

Can I save money by flying with a layover from Hartford to Florida Keys?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $374, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Hartford to Florida Keys?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Hartford to Florida Keys, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Hartford to Florida Keys is November, when tickets cost $49 (return) on average. On the other hand, the most expensive months are February and April, when the average cost of round-trip tickets is $930 and $665 respectively.

What’s the cheapest day of the week to fly from Hartford to Florida Keys?

The average price of all round-trip flights from Hartford to Florida Keys clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Florida Keys on a Thursday and more expensive on a Monday. On your return trip to Hartford, you should consider flying back on a Friday, and avoid Sundays for better deals.

How far in advance should I book a flight from Hartford to Florida Keys?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Hartford to Florida Keys, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Hartford to Florida Keys, you should book around 2 weeks before departure, which saves you about 20% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$99
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly with an average 30% increase in price.
Flight from Hartford to Miami

FAQs - booking Florida Keys flights

  • How does KAYAK find such low prices on flights from Hartford to Florida Keys?

    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 Hartford to Florida Keys.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Hartford to Florida Keys?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Hartford to Florida Keys 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 Hartford to Florida Keys?

    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 from Hartford to Florida Keys with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Hartford to Florida Keys?

    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 from Hartford to Florida Keys up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Florida Keys

  • Looking for a cheap flight? 25% of our users found tickets from Hartford to the following destinations at these prices or less: Miami $224 one-way - $383 round-trip

Reviews of the top 5 airlines serving from Hartford to Florida Keys

 
See real verified KAYAK customer reviews for airlines flying from Hartford to Florida Keys. 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 Hartford to Florida Keys? 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.
7.9
SouthwestOverall score based on 4305 reviews
8.1Boarding
8.6Crew
8.0Comfort
7.5Entertainment
7.0Food
Airline reviews

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

2.0 MediocreAnonymous, May 2026
SEA - SMF
Read more Southwest reviews

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

Overall Good! The weather delayed our takeoff from Atlanta and our arrival in Miami! If Mother Nature can mess up a flight she will do it every time!

N Everything was perfect from boarding to assistance to baggage in Tampa

Snacks and included beverages were appreciated. Boarding went smoothly. Plenty of overhead bin space. Seats get very uncomfortable after a couple of hours. After waiting 10 painful minutes for my walker, a very nice Delta guest agent pushed me in a wheelchair to the gate. It was finally delivered to me after another 15 minutes . Our checked bag was on the carousel long b4 I was able to retrieve it. Fortunately it was still there but somewhere along the way the straps we used to secure it were removed and and were not reattached. Wish I had made note of the agents name.

The whole experience was excellent. As it most often is with Delta

We waited an hour on the runway to get a gate in Orlando

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

The staff on board and gate was nice - a welcome change from the usual. We also arrived early, which was a great benefit, given that it takes 30 minutes plus to get bags at SRQ.

They took all carry-on luggage from Groups 6 -9 - I was group 5 and waiting in line to board - they made me check my luggage too. That then went to baggage claim and delayed departure from the airport. There was overhead room in my seating area - Delta over reacted. Also, had a gentleman next to me that took up 1/2 my seat.

Sorry I didn't realize I was writing a review for each leg. Please see my previous review - it applies to the entire flight, not just a single leg.

boarded at 5:30 pm, pushed away from gate at 6pm ... takeoff was not until ~6:45pm; disappointing

Excellent price. Everything on time. two bad parts. Kayak said I couldn't sign in for the flight online, but I got an email at the same time from Jet Blue and they let me sign in online. Second bad part was that, although I had provided my known traveler number, neither of my boarding passes, for this flight and the previous one, had TSA pre-check showing.

Jet blue was great But the Jayak system Wasa pure nightmare and wasted so much of my time and energy by not giving me a way to access jet blue to check in the flight back I didn’t even get the number confirmation code 24 hours before. Because I didn’t receive the email with the confirmation code I could NoT CHECk IN. I spoke to a kayak third party and they informed me I could not carry a carry on, on the flight which caused me so much extra stress it was just too much. You can be sure I will not be using it recommending your site. Again.

There was a screen but no earphones that could use the older input so I could listen to anything.

My experience with JetBlue was fine BUT I am very upset with Kayak! JetBlue had delayed our scheduled departure by an hour and you NEVER notified me of the change. I did not hear directly from JetBlue because the trip was booked through Kayak, a mistake I will not repeat. Your reminder of the our trip last week still had the WRONG departure time. Our return trip has also changed, and again no notice from you.

Jet blue just had great service overall! Only a little turbulence heading out of Austin, otherwise the jet stream helped the speed of the trip!

Boarding was done extremely poorly, with huge crowds gate loiterers blocking people from boarding, multiple lines of people trying to merge into one line. One of the male flight attendants who was doing drink service was not happy about having to let a passenger back to their seat and was unnecessarily sassy about it. I thought he was pretty entitled and not a great ambassador for JetBlue

My experience with Jet Blue was wonderful. My experience with Kayak sucked and will never use again.

We were delayed and had to circle due to weather and had to divert for fuel. While I understand that you can’t control the weather I would have appreciated knowing that the crew wasn’t going to run out of hours and then having to spend the night in the Raleigh airport.

Messy plane that was falling apart Small screens that didn't work

Flight was good wish there were more snacks options for such a long flight but stewardesses were very pleasant as was flight crew.

Cancelled BOYH legs of our flight home 30 min before initial boarding

Flight left early and arrived 30 MINUTES early at the destination. Smooth trip.

I was able to get the AA customer Service desk to put me on an earlier flight without any issues.

Incredibly delayed. First delay was due to plane coming in being late. Resulted in 30 minute delay. Boarded and then had multiple mechanical issues. Was on plane for an hour until they told people they could get off if they wanted but couldn't come back. Then gate agent rushed in and said they had lost control of who went off and we would all have to deplane and then get back on. They said flight had not been cancelled. Then while sitting waiting to board again they announced it would take two hours to get new plane and to wait at new gate. New plane arrived, reboarded only to find out that pilots had timed out. Waited for new pilots. In that time one of the flight attendants timed out. Never received food or water while waiting. Was confusing mess as to what was happening. Even flight attendants and gate agents were getting frustrated. Almost 6 hours delayed. Called American to received flight credit but can't get anywhere as Kayak reservation and don't have a ticket number. Reached out to Kayak but never heard back.

Very disappointing. Flight was delayed by 1.5 hours and food options are very underwhelming even for first class seats (same food given to economy seats)

Was not able to do a online check-in because the American Airlines system doesn't store our visa or other passport information, allowing us to have a trouble-free check-in. We were forced to have to check-in at the counter which Changes are upgrade status given that we were not able to check in much earlier.

Incoming flight was delayed, delaying boarding. It then took 30 mins to take off. Took 20 mins to get to a gate because they changed the gate last minute, crew weren’t ready so there was no one staffed to work the jet bridge. Boarding was so disorganized as is usual with American because everyone just stands around the gate regardless of boarding group.

I would have liked vegetarian and gluten free options for evening dinner time flight. I would have like a pillow on the international overnight flight . The veg wrap and oaten desert on the international flight was good

We hoarded. Then we deplaned. Then we waited for 10 hours in the MSP airport due to a wheel misfunction. We understand safety but communication between crew and airport staff was horrible. When we did finally board, we were rushed on and because we were waiting for a “fresh” pilot and crew, we sat in a roasting plane with no A/C for an hour. My question is why was this flight not cancelled right away when they knew this would be a huge issue OR, why did AA not get a substitute plane, considering this was already a full flight? To me, this appears to be a complete breakdown in leadership and utter systems failure. The compensation for completely disrupting travel plans for hundreds, which we paid dearly for, was measly. While we appreciated the lodging for the night, $12 in meal vouchers isn’t going to sustain anyone for over 12 hours. “We apologize; our hands are tied” is no longer an acceptable explanation. We are so completely turned off by this experience and will definitely seek alternative avenues when we need to fly.

Check in was rough because the check in crew did not know how to manage my international visa documents. Required a long process and 4 people to finally be able to proceed to security. They told us incorrect information several times before acknowledging we did indeed have everything we needed from the start.

Frontier scheduled a 40 minute connection in DEN. What they failed to mention was that they “close the doors” 20 mins prior to departure, which means you only have 20 mins. Not enough time. Possibly against DOT regulations. Filing complaint.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

They didn’t offer a water, even after I asked

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

Everything you need to know for your flight to Florida Keys

Information on your arrival and departure airports