MKE - SXM

$232 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 1/9. 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
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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

Thu, Dec 11 - Tue, Dec 16
American Airlines Logo
6:46 pm - 1:55 pmMKE-SXM
17h 09m1 stop
American Airlines Logo
3:35 pm - 9:22 pmSXM-MKE
7h 47m1 stop
$612American Airlines
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Wed, Oct 29 - Wed, Nov 5
American Airlines Logo
2:05 pm - 1:37 pmMKE-SXM
22h 32m2 stops
American Airlines Logo
3:20 pm - 8:00 amSXM-MKE
18h 40m2 stops
$617American Airlines
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Sat, Nov 29 - Sat, Dec 6
American Airlines Logo
6:48 pm - 2:00 pmMKE-SXM
17h 12m1 stop
American Airlines Logo
3:35 pm - 9:22 pmSXM-MKE
7h 47m1 stop
$648American Airlines
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Sat, Nov 29 - Sat, Dec 6
American Airlines Logo
6:48 pm - 4:20 pmMKE-SXM
19h 32m2 stops
American Airlines Logo
3:35 pm - 10:28 amSXM-MKE
20h 53m2 stops
$653American Airlines
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Wed, Dec 24 - Wed, Dec 31
American Airlines Logo
6:48 pm - 12:30 pmMKE-SXM
15h 42m2 stops
American Airlines Logo
2:15 pm - 2:52 pmSXM-MKE
26h 37m1 stop
$688American Airlines
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Wed, Oct 29 - Wed, Nov 5
Delta Logo
5:17 am - 1:49 pmMKE-SXM
7h 32m1 stop
Delta Logo
4:14 pm - 11:55 pmSXM-MKE
9h 41m1 stop
$727Delta
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Sat, Jan 17 - Sat, Jan 24
Delta Logo
5:45 am - 2:56 pmMKE-SXM
7h 11m1 stop
Delta Logo
5:16 pm - 11:27 pmSXM-MKE
8h 11m1 stop
$737Delta
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Sat, Sep 13 - Sat, Sep 20
Delta Logo
5:40 am - 1:50 pmMKE-SXM
7h 10m1 stop
Delta Logo
3:20 pm - 11:48 pmSXM-MKE
9h 28m1 stop
$783Delta
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Wed, Dec 24 - Wed, Dec 31
American Airlines Logo
6:48 pm - 12:30 pmMKE-SXM
15h 42m2 stops
American Airlines Logo
3:20 pm - 9:44 amSXM-MKE
20h 24m2 stops
$797American Airlines
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Thu, Dec 11 - Tue, Dec 16
 Logo
6:00 am - 4:00 pmMKE-SXM
32h 00m2 stops
 Logo
5:00 pm - 7:03 pmSXM-MKE
28h 03m3 stops
$1,184
Find Deal
Booking Insights

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 American Airlines ($612) and Delta ($727).

Good to know

Low seasonMay
Cheapest flight$232
Best time to beat the crowds with an average 38% drop in price.
Most popular time to fly and prices are also 13% 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 $232 for a one-way ticket and $612 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 $684 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 $717 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.

Reviews of the 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 7980 reviews
7.9Comfort
8.2Boarding
8.5Crew
7.9Entertainment
7.3Food
Airline reviews

Delayed and took off even later than the scheduled delay time

8.0 ExcellentAnonymous, Jul 2025DTW - SEA
Read more Delta reviews

Delayed and took off even later than the scheduled delay time

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Only issue was with seating. The economy fare we purchased did say there was no guarantee the three people in our party would be seated together, and we were not. At the gate, the agent told us more specifically, the fare we purchased meant we would be seated in middle seats only. This should just be made more obvious.

Great experience on Delta. Staff from baggage check to flight attendants were very courteous and professional. My only issue was a personal preference for pretzels instead of the chips and cookies that were offered.

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

Everything was good until we were boarding our connection flight in Atlanta, we were told to gate check our carry-on, but when we got inside the plane, there was plenty of room in the overhead.

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

Flight was canceled, and no effort was made to help with rebooking, no hotel vouchers, no car transportation and minimal food voucher and most places for food were closed by the time the voucher was given. Waited for 3 hours for bags. Simply the worst travel experience I have ever had

Very poor delay in dfw was really bad n long

Our flight was 1.5 hours delayed. There was no weather for the inbound flight, so I don't understand why. This meant a VERY late arrival and only a quick nap before my morning flight.

Because of rescheduling, they had to put me on a flight that didn't go through Dallas

It was very difficult to stretch my knee out and I am very short. I also had a torn tendon in my knee which made it extra uncomfortable anyways. My husband is 6'2" and I can't imagine him flying in that plane.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

Flight was cancelled 3 hrs AFTER etd. Thetefore Missed connection from JFK to New Zealand . No accommodation provided… This cost ne aporox 1000 USD in extra expenses and turned whst should have been a 24 hr trip ftom Boston - New Zealand into a VERY expensive , late 70+ hr nightmare … Complete nonsense!!!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

The plane was broken so we had to change planes.

The flight got delayed 2.5 hrs due to a maintenance issue that cause a domino effect. American should have spare planes for when something like this happens.

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

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