$69 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 2/20. 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.
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% 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 Milwaukee to Florida Keys

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Miami
Miami1 stop$239
Key West
Key West1 stop$255
Miami
Miami1 stop$239
Key West
Key West1 stop$255

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

Fri, Feb 27 - Mon, Mar 9
Frontier Logo
6:20 pm - 12:42 am
MKE
-
MIA
5h 22m
1 stop
Frontier Logo
5:05 am - 10:03 am
MIA
-
MKE
5h 58m
1 stop
$239Frontier
Fri, Feb 27 - Mon, Mar 9
Frontier Logo
6:20 pm - 12:42 am
MKE
-
MIA
5h 22m
1 stop
Frontier Logo
5:50 am - 6:51 pm
MIA
-
MKE
14h 01m
1 stop
$249Frontier
Wed, Mar 4 - Wed, Mar 11
American Airlines Logo
6:01 am - 10:22 am
MKE
-
MIA
3h 21mnonstop
American Airlines Logo
9:19 pm - 11:59 pm
MIA
-
MKE
3h 40mnonstop
$250American Airlines
Tue, Feb 24 - Sat, Feb 28
Delta Logo
1:35 pm - 8:44 pm
MKE
-
MIA
6h 09m
1 stop
Delta Logo
7:00 am - 12:35 pm
MIA
-
MKE
6h 35m
1 stop
$251Delta
Sun, Mar 8 - Thu, Mar 12
Multiple Airlines Logo
9:01 pm - 12:26 pm
MKE
-
EYW
14h 25m
1 stop
Multiple Airlines Logo
9:46 am - 8:06 pm
EYW
-
MKE
11h 20m
1 stop
$255Multiple Airlines
Wed, Mar 4 - Wed, Mar 11
American Airlines Logo
6:01 am - 10:22 am
MKE
-
MIA
3h 21mnonstop
American Airlines Logo
3:53 pm - 11:07 pm
MIA
-
MKE
8h 14m
1 stop
$260American Airlines
Sat, Feb 28 - Tue, Mar 3
United Airlines Logo
9:44 am - 10:35 pm
MKE
-
MIA
11h 51m
2 stops
United Airlines Logo
6:00 am - 3:35 pm
MIA
-
MKE
10h 35m
2 stops
$261United Airlines
Sat, May 2 - Wed, May 6
Delta Logo
12:32 pm - 7:40 pm
MKE
-
EYW
6h 08m
1 stop
Delta Logo
6:19 pm - 11:57 pm
EYW
-
MKE
6h 38m
1 stop
$269Delta
Wed, Mar 4 - Wed, Mar 11
United Airlines Logo
9:44 am - 5:29 pm
MKE
-
MIA
6h 45m
1 stop
United Airlines Logo
4:10 pm - 9:50 pm
MIA
-
MKE
6h 40m
1 stop
$270United Airlines
Sun, Feb 15 - Thu, Feb 19
Multiple Airlines Logo
6:37 pm - 12:26 pm
MKE
-
EYW
16h 49m
1 stop
Multiple Airlines Logo
9:46 am - 9:43 am
EYW
-
MKE
24h 57m
1 stop
$271Multiple Airlines
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.

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 $415, 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 $297 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $499 and $446 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 36% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 2 weeks before departure.

Good to know

Low seasonJuly
Cheapest flight$69
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 26% increase in price.
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.

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

    The cheapest time of day to fly to Florida Keys is generally in the afternoon, when round-trip flights cost $369 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 $608.

Top tips for finding cheap flights to Florida Keys

  • Looking for a cheap flight? 25% of our users found tickets from Milwaukee to the following destinations at these prices or less: Miami $194 one-way - $341 round-trip

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 4267 reviews
8.1Boarding
7.5Entertainment
8.0Comfort
8.6Crew
7.0Food
Airline reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

10.0 ExcellentAnonymous, Jan 2026
PHX - MDW
Read more Southwest reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

The flight was delayed and oversold. I volunteered to give up my seat for compensation. Thinking I could get a good night's sleep instead of arriving home at 2 am. It took over an hour to get the new reservation confirmed, three different gate attendants, and two red coats. It took even longer to confirm the overnight hotel, and when I arrived, the line was 45 minutes long, with two people checking in, and at least 15 people slowly, very slowly—no food except frozen convenience food, no coupon for food from airlines. Slept, headed back to the airport, and that flight had an equipment change and a gate change just as they were about to board. It took an additional hour to board as they cleaned the plane from storage.

Probably not the fault of Delta but there was delay after delay after delay and I ended up getting home 4 hours later then I should have at 1:30 in the morning

Comfort Plus seat 11E seemed smaller than prior flights. The movie selection is good. Watched most of the most recent Tron movie. I'll watch the remaining part later as my movie is saved in the Delta Seatback Experience.

Delta is a good airline. I've never had an issue with Delta. I'll continue to fly with them until they show me that I shouldn't.

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

First, Delta needs more flights to/from Miami. Second, a 1000pm leaving at 1230pm is unacceptable from their biggest airport world hub. Another aircraft could have been used such as the aircraft scheduled to be used in the morning for that exact same route. Yes, I did get me there but the lack of sleep the next day didn't help me enjoy my entire trip since I was busy with activities during the weekend. This can be and is expected from Spirit (going bankrupt) and Frontier (despite they're nickel and dimers). But from Delta's World Hub? That's totally unacceptable!

Service in business class was not impressive. I ordered coffee with dinner and then watched other people get 2 refills before I got my 1 cup of coffee, and only after I pressed the attendant button overhead. Furthermore, the seats in the forward cabin need maintenance on this 737-800: the upholstery is detaching from the seat frame, at least on the backs of seats 1C, 1D.

I truly love flying with Delta. They have always treated me with the upmost respect

Our flight attendant in FIRST CLASS was one of the worst I’ve ever had. She was not at all pleasant, nor particularly good at her service.

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

HORRIBLE, my initial flight was cancelled, they made me pay $200 extra dollars and that got cancelled as well! After 6 cancellations I decided to get a refund because I needed to get home to my babies. Out of $1000+ dollars they offered me only $40 in refund! Totally unacceptable! The flight that they cancelled I was able to fly it on another airline. I had to spend $400 on one way tickets just to get home! I’m still getting the runaround.

First class ticket gets you a choice of chips or nuts. . Just like economy Southwest. Also no screen in the seats. This is first class???!

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Flight arrived 30 min early and bag was waiting at the baggage pickup. United Club HNL was one of the nicest in the system

Unfortunately weather delayed our flight waiting for our plane to arrive and due to a little snow time was needed to deice the plane so departure was very delayed and I missed the connecting flight

Very good. Because of the delays with my previous flight, I missed my connection, but I was able to book another flight through the United app easily.

I wish there were outlets to charge my iPhone. The crew was great; we had a female pilot who was great with explaining what was happening and delays,

No gates avail at DFW so our incoming had to wait 30 mins for a plane to push back because they Had mechanical. We boarded 90 mins delayed and then we had a mechanical. Come on American…do better. Also at my seat the tray table had not been cleaned. Floor had not been cleaned. But captain and flight Att were very picture and apologetic.

Crew was helpful and cheerful especially when they had no refreshments to work with. The plane was never serviced and had nothing but limited water and coffee onboard. For the price point, a concern of services.

It was a little concerning to hear the ground crew arguing with the flight crew over baggage space. Instead of taking them and checking them, they started checking for space in the first class cabin moving items around like the flight crew didn't know what they were doing. I was embarrassed for them.

On the plus side, crew was attentive, drinks were cold, and in-flight entertainment selection was better than some other airlines. On the negative aide, Plane was delayed almost an hour, either no announcements from the gate crew. Biscoff cookies are gross, appreciate airlines that give a choice. Also, crew had no personality or enthusiasm at all.

UGH I HAD TO MISS MY FIRST FLIGHT TO TAMPA CAUSE OF THE 10 MINUTE DELAY OF THE ORLANDO TO MIAMI ONE SO THEY HAD ME GET ANOTHER TICKET. I AM NOT HAPPY AT ALL BECAUSE IT MADE ME MISS MY CONNECTING FLIGHT FROM TAMPA TO LONDON AND FORCED ME TO MISS A DAY AT MY ROOM IN THE UK.

Wish they didnt delay off-boarding for 10 minutes so i could connect to my flight from miami to tampa

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

I bought wifi and most of the flight could not even use it my apps would just spin. I couldn't even listen to music. super frustrating.

I got sick nothing contagious but distressing and the care I received by Kayla? Keighly the flight attendant will be memorable for ever. Thank You

Waaay too small plane. They also need to up the size of the overhead bins. I would love to keep me 3k with of camera equipment in my hard case baggahe instead of it being thrown into the belly of the plane

Everything was OK, the deicing took a long time, our connections were almost missed.

Flight was cancelled. But kayak thought it was still on time.

Spirit was on time. They maintained updates and information. The crew was friendly and professional. Because this is a budget friendly airline, they have dispensed with a lot of frills and part of that comes with a price, for example, the seats are not quite as comfortable as others. I am ok with a pay for beverage and snack service as I prefer my own anyway so this was not a concern. I thought overall, having a great flight crew and on time service was definitely worth losing some of the frills from other carriers.

You can’t beat Spirit’s prices on tickets, especially with the positive experience that comes with it! I appreciated the timeliness of Spirit airlines. The crew in the airport was very kind and wished you a good flight by name. The crew on the flight was attentive and friendly. Overall, I am very pleased with my experience with Spirit.

This was my best experience with spirit. I flew you guys 4 times and I must say this was the BEST

I didn't have a flight because of a ticking problem that was discovered at the airport at checkin for the initial flight of the round trip.

Flight was delayed would have liked it to have been on time. I didn't experience the food or entertainment but the boarding process was smooth and the flight crew worked well together and did a great job!

Cheap, only one short delay. No issues despite bad weather. Able to take a big backpack for free.

I know Spirit gets a lot of criticism, but I've taken three flights recently and all were very good, and tremendous value. On my most recent one, they randomly assigned me to a very comfortable exit row seat! The flight was on time and the boarding process was smooth, and the crew was friendly. No complaints!

My experience with spirit was horrible I had to spend a extra $100 to check in my bag when I already purchased my ticket even when I got to my gate to get my seat the attendant didnt say anything until I was boarding the plane..also to make matters worst I been flying from Florida to New york and Florida to Atlanta often this was my 4th trip to Atlanta with the same bag and never had this problem till yesterday so im extremely upset and I wasnt even giving a reason for the change the attendant just gave a attitude and wouldn't answer me at all

Everything you need to know for your flight to Florida Keys

Information on your arrival and departure airports