MKE - SXM

$178 Find Cheap Flights from Milwaukee to Simpson Bay

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 Simpson Bay departing on 7/11. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Simpson Bay

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Milwaukee to Simpson Bay, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Milwaukee to Simpson Bay, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 20% 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.

Flights Deals
Useful Info
Flights Deals

Cheap Flights from Milwaukee to Simpson Bay (MKE-SXM)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Milwaukee 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 Milwaukee to Simpson Bay

Sat, Sep 13 - Sat, Sep 20
Spirit Airlines Logo
8:51 pm - 2:24 pmMKE-SXM
40h 33m3 stops
Spirit Airlines Logo
3:27 pm - 6:40 amSXM-MKE
40h 13m3 stops
$607Spirit Airlines
Find Deal
Mon, Oct 20 - Fri, Oct 24
American Airlines Logo
5:19 pm - 1:15 pmMKE-SXM
18h 56m2 stops
American Airlines Logo
4:10 pm - 11:44 amSXM-MKE
20h 34m2 stops
$610American Airlines
Find Deal
Sat, Sep 13 - Sat, Sep 20
American Airlines Logo
3:47 pm - 1:19 pmMKE-SXM
20h 32m2 stops
American Airlines Logo
2:35 pm - 11:00 pmSXM-MKE
9h 25m1 stop
$617American Airlines
Find Deal
Sat, Sep 13 - Sat, Sep 20
Delta Logo
6:00 am - 1:50 pmMKE-SXM
6h 50m1 stop
Delta Logo
3:15 pm - 11:25 pmSXM-MKE
9h 10m1 stop
$637Delta
Find Deal
Fri, Nov 28 - Sat, Dec 6
American Airlines Logo
3:11 pm - 12:10 pmMKE-SXM
18h 59m2 stops
American Airlines Logo
3:35 pm - 10:28 amSXM-MKE
20h 53m2 stops
$642American Airlines
Find Deal
Sat, Jul 26 - Sat, Aug 2
Spirit Airlines Logo
4:37 pm - 2:00 pmMKE-SXM
44h 23m3 stops
Spirit Airlines Logo
3:05 pm - 3:42 pmSXM-MKE
25h 37m2 stops
$653Spirit Airlines
Find Deal
Sat, Jul 26 - Sat, Aug 2
Spirit Airlines Logo
4:37 pm - 2:00 pmMKE-SXM
44h 23m3 stops
Spirit Airlines Logo
3:05 pm - 3:42 pmSXM-MKE
25h 37m3 stops
$733Spirit Airlines
Find Deal
Sat, Jul 26 - Sat, Aug 2
American Airlines Logo
6:31 pm - 1:49 pmMKE-SXM
18h 18m2 stops
American Airlines Logo
4:25 pm - 9:33 amSXM-MKE
18h 08m2 stops
$745American Airlines
Find Deal
Sat, Jul 26 - Sat, Aug 2
American Airlines Logo
7:05 am - 1:25 pmMKE-SXM
29h 20m1 stop
American Airlines Logo
4:25 pm - 9:33 amSXM-MKE
18h 08m2 stops
$754American Airlines
Find Deal
Fri, Nov 28 - Sat, Dec 6
 Logo
7:00 am - 4:15 pmMKE-SXM
31h 15m3 stops
 Logo
1:05 pm - 5:36 pmSXM-MKE
30h 31m2 stops
$1,248
Find Deal
Useful Info

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

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

Which airlines provide the cheapest flights from Milwaukee to Simpson Bay?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Milwaukee to Simpson Bay were found on Spirit Airlines ($607) and American Airlines ($610).

Good to know

Low seasonMay
High seasonMarch
Cheapest flight$178
Best time to beat the crowds with an average 38% drop in price.
Most popular time to fly and prices are also 12% lower on average.
Flight from Milwaukee to Simpson Bay

When to book flights from Milwaukee to Simpson Bay

Are your dates flexible? Find out the best times to travel from Milwaukee 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 Milwaukee to Simpson Bay

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

    In the last 3 days, the lowest price for a flight from Milwaukee to Simpson Bay was $178 for a one-way ticket and $607 for a round-trip.

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

    A passport is required to fly from Milwaukee to Simpson Bay.

  • Which airports will I be using when flying from Milwaukee to Simpson Bay?

    On your way to Simpson Bay, you’ll fly out from Milwaukee-Mitchell. You’ll be landing at Simpson Bay Princess Juliana.

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

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

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

    SkyTeam, and oneworld are the airline alliances operating flights between Milwaukee and Simpson Bay, with SkyTeam being the most commonly used for this route.

  • Which is the best airline for flights from Milwaukee to Simpson Bay, Delta or American Airlines?

    The two airlines most popular with KAYAK users for flights from Milwaukee to Simpson Bay are Delta and American Airlines. With an average price for the route of $673 and an overall rating of 8.0, Delta is the most popular choice. American Airlines is also a great choice for the route, with an average price of $721 and an overall rating of 7.2.

  • How does KAYAK find such low prices on flights from Milwaukee 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 Milwaukee to Simpson Bay.

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

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

Top airlines flying from Milwaukee to Simpson Bay

 
See real verified KAYAK customer reviews for airlines flying from Milwaukee 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 Milwaukee 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.
8.0
DeltaOverall score based on 7950 reviews
8.2Boarding
7.3Food
8.5Crew
7.9Comfort
7.9Entertainment
Airline reviews

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

10.0 ExcellentHartaj, Jun 2025EWR - RDU
Read more Delta reviews

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Great flight! Only complaint I had was that I didn’t get breakfast that morning because I don’t eat eggs for breakfast.. I ate an energy bar I bought in the airport which I had never done before. Otherwise, another great Delta flight!

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

The entertainment and wifi mostly didn't work on this flight.

Terrible entertainment system - kept freezing and audio kept cutting out. Snacks were mediocre at best for a 5 hour flight.

The check in and bag drop off for Sky Priority members is slow. The Clear security was also slow - a TSA issue.

I am still upset that my bag was lost on a recent trip to Rome ; we were inconvenienced and out €150 Euros ; delta has refused to reimburse us

It was one of my worst flight ever. First they were changing the gate for at least 4 times, changing from gate D7 to D12 to D44. Considering the size of the Miami Airport, we are talking about long distance and the train at the airport was not working. Then the flight was delayed around one hour. Then finally we boarded into the plane and when everybody was seated, there was an announcement that there is an issue with one of the tire of the plane, so we all had to get out of the plane with our belongings, to replace the tire. So we had around 2.5-hour delay

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

Honestly, I haven’t flown American in years, probably due to the pandemic and my being unable to travel for certain periods in the last two years, but it was a good experience to dig out or obtain a new American Airlines account after many years of traveling for business with American in the past.

The plane was probably full boarding was easy. We were able to check our carry-on luggage for free. It was a return flight through Philly to LA. Never saw a stewardess do a demonstration of emergency Procedures. I think my flight was pretty full

Plane, flight, crew, captain were all great. The first flight had a Chipotle box lunch...delicious.

Plane, flight, crew, captain were all great. The first flight had a Chipotle box lunch...delicious. this return flight not as tasty, but filling.

The flight was 2 hour delayed, otherwise everything was excellent. The delay was due to the hourly limit requirement so given that as a reason, I'm happy with the flight!

Weather delay for 2.5 hours followed by half hour crew delay, did not have ginger ale, uncomfortable seats

Flight was full, and would have preferred an aisle seat, but due to getting a late ticket ,the seat I had was adequate. The flight crew were very help full and hard working. Food and drink were excellent for the 11hr flight. Overall I was pleased with flight, and would recommend British Airways again.

So awful Unreliable Unfriendly Bad Mad Mean Smelly Hot Late Overbooked Understaffed Expensive Cramped Narcs If they were a fruit they’d be rotten durian

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

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.