$86 Find Cheap Flights from Milwaukee 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 Milwaukee to Florida Keys departing on 5/23. 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 Milwaukee to Florida Keys.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Milwaukee to Florida Keys.
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Cheap Flights from Milwaukee to Florida Keys

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Miami
Miami1 stop$251
Key West
Key West1 stop$231
Miami
Miami1 stop$251
Key West
Key West1 stop$231

Book Cheap Milwaukee 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 Milwaukee 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 Milwaukee to Florida Keys

Tue, May 26 - Tue, Jun 2
American Airlines Logo
7:00 am - 4:07 pm
MKE
-
EYW
8h 07m
1 stop
American Airlines Logo
5:37 pm - 11:10 pm
EYW
-
MKE
6h 33m
1 stop
$231American Airlines
Tue, May 26 - Tue, Jun 2
American Airlines Logo
7:00 am - 7:10 pm
MKE
-
EYW
11h 10m
2 stops
American Airlines Logo
7:29 pm - 11:59 pm
EYW
-
MKE
5h 30m
1 stop
$236American Airlines
Fri, May 29 - Wed, Jun 3
Delta Logo
6:25 pm - 12:47 am
MKE
-
MIA
5h 22m
1 stop
Delta Logo
7:05 am - 11:38 am
MIA
-
MKE
5h 33m
1 stop
$251Delta
Wed, Jun 10 - Tue, Jun 16
American Airlines Logo
6:13 am - 6:49 pm
MKE
-
EYW
11h 36m
2 stops
American Airlines Logo
1:39 pm - 11:10 pm
EYW
-
MKE
10h 31m
2 stops
$261American Airlines
Tue, Jul 28 - Sat, Aug 1
Delta Logo
10:11 am - 5:23 pm
MKE
-
EYW
6h 12m
1 stop
Delta Logo
7:50 am - 11:51 am
EYW
-
MKE
5h 01m
1 stop
$265Delta
Sat, Jun 6 - Mon, Jun 8
Multiple Airlines Logo
12:29 pm - 11:25 am
MKE
-
EYW
21h 56m
2 stops
Multiple Airlines Logo
3:25 pm - 7:58 am
EYW
-
MKE
17h 33m
1 stop
$271Multiple Airlines
Sat, Jun 6 - Mon, Jun 8
Delta Logo
7:09 am - 2:09 pm
MKE
-
EYW
6h 00m
1 stop
Delta Logo
6:24 pm - 11:59 pm
EYW
-
MKE
6h 35m
1 stop
$275Delta
Tue, May 26 - Tue, Jun 2
Delta Logo
10:13 am - 5:23 pm
MKE
-
EYW
6h 10m
1 stop
Delta Logo
2:00 pm - 9:02 pm
EYW
-
MKE
8h 02m
1 stop
$280Delta
Tue, May 19 - Tue, May 26
Southwest Logo
8:00 am - 4:50 pm
MKE
-
MIA
7h 50m
1 stop
Southwest Logo
5:45 pm - 10:50 pm
MIA
-
MKE
6h 05m
1 stop
$351Southwest
Tue, May 19 - Tue, May 26
Southwest Logo
9:15 am - 8:40 pm
MKE
-
MIA
10h 25m
2 stops
Southwest Logo
5:45 pm - 10:50 pm
MIA
-
MKE
6h 05m
1 stop
$356Southwest
Booking Insights

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

Get data-powered insights and trends into flights from Milwaukee 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 Milwaukee 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 in the afternoon, when round-trip flights cost $472 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 $606.

Can I save money by flying with a layover from Milwaukee 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 $434, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Milwaukee 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 Milwaukee to Florida Keys is September, when tickets cost $42 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $248 and $184 respectively.

How far in advance should I book a flight from Milwaukee 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 Milwaukee 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 Milwaukee to Florida Keys, you should book around 2 weeks before departure, which saves you about 34% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 7 weeks before departure.

Good to know

Low seasonJune
Cheapest flight$86
Best time to beat the crowds but there is an average 6% increase in price.
Most popular time to fly and prices are also 3% lower on average.
Flight from Milwaukee to Miami

FAQs - booking Florida Keys flights

  • How does KAYAK find such low prices on flights from Milwaukee 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 Milwaukee to Florida Keys.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Milwaukee 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 Milwaukee 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 Milwaukee 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 Milwaukee 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 Milwaukee to Florida Keys up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

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

 
See real verified KAYAK customer reviews for airlines flying from Milwaukee 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 Milwaukee 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.
8.0
SouthwestOverall score based on 4314 reviews
7.0Food
8.1Boarding
8.6Crew
7.5Entertainment
8.0Comfort
Airline reviews

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

10.0 Excellentlarry, Apr 2026
LGB - PHX
Read more Southwest reviews

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?

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

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

Booked through Kayak Business, had a seat in middle and towards back due to booking rate, not comfortable.

Was great in general, try to respect time and excuses when slight changes have been made, appreciated!

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Outstanding service, efficient & friendly crew, flight was safe, comfortable & on time

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

They told us yesterday APR21st that they were cleaning the plane and we got delayed. After that they said they didn't had any crew for the flight so they cancelled the flight till next day.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

I've been flying American mostly, and it's been very frustrating. This united flight makes me realize maybe the issue isn't flying, but the airline. United was a significantly better experience. The plane was more comfortable, with a normal amount of leg room (vs the ridiculous reductions AA has made), more comfortable seats, screens to watch movies. It was a much better experience!

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.

Mechanical issue delayed us 2hrs and then once we landed sat on tarmac for 30mins because someone left a vehicle in front of the gaye

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.

The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!

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 !!!!!!!

I am writing to express my disappointment with my recent Frontier Airlines flight. I was charged $99 at the gate because my bag was said to be too large, yet once onboard there was no available overhead bin space, and I was required to place the bag under the seat in front of me anyway. This made the charge feel unnecessary and unfair. Additionally, before the flight even took off, I was asked to move from the seat I paid for into a middle seat so another passenger and her cat could have my seat to themselves. I was not offered compensation or an explanation for being moved from a paid seat. Between the unexpected bag fee and being forced to give up my seat, this experience fell well below acceptable customer service standards. I would appreciate a review of this situation and appropriate compensation.

Everything you need to know for your flight to Florida Keys

Information on your arrival and departure airports