Cheap flights from Milwaukee to Simpson Bay from $215
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Milwaukee to Simpson Bay departing on 3/1. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Discover deals from 900+ travel sites with momondo.
Find the cheapest flights from Milwaukee to Simpson Bay
Cheap round-trip flights
Cheap one-way flights
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.Price Alerts
Price Alerts
Not ready to book? to track prices.United Airlines flights from Milwaukee to Simpson Bay
Our best United Airlines deals on Milwaukee to Simpson Bay flight tickets
Delta flights from Milwaukee to Simpson Bay
Our best Delta deals on Milwaukee to Simpson Bay flight tickets
momondo Fare Finder
Use the filters below to find and compare flights from Milwaukee to Simpson Bay that are best for you.
Fly from
Fly to
Route
Depart
Return
MilwaukeeSimpson Bay
MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana
MKESXM
Milwaukee-Mitchell
Sat 1/30
1:38 pm-12:34 pm
2 stops20h 56m
Simpson Bay Princess Juliana
Fri 2/5
1:34 pm-8:23 am
2 stops20h 49m
MilwaukeeSimpson Bay
MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana
MKESXM
Milwaukee-Mitchell
Sat 1/30
5:00 am-2:50 pm
1 stop7h 50m
Simpson Bay Princess Juliana
Fri 2/5
3:35 pm-11:55 pm
1 stop10h 20m
MilwaukeeSimpson Bay
MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana
MKESXM
Milwaukee-Mitchell
Sat 2/20
6:40 pm-2:40 pm
1 stop18h 00m
Simpson Bay Princess Juliana
Sat 2/27
5:25 pm-9:22 am
1 stop17h 57m
MilwaukeeSimpson Bay
MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana
MKESXM
Milwaukee-Mitchell
Sun 2/21
6:40 pm-2:40 pm
1 stop18h 00m
Simpson Bay Princess Juliana
Sat 2/27
5:25 pm-9:22 am
1 stop17h 57m
MilwaukeeSimpson Bay
MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana
MKESXM
Milwaukee-Mitchell
Mon 3/1
2:23 pm-1:50 pm
2 stops21h 27m
Simpson Bay Princess Juliana
Sun 3/7
2:20 pm-8:54 pm
1 stop8h 34m
MilwaukeeSimpson Bay
MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana
MKESXM
Milwaukee-Mitchell
Mon 3/1
6:45 pm-1:50 pm
1 stop17h 05m
Simpson Bay Princess Juliana
Sun 3/7
2:20 pm-8:54 pm
1 stop8h 34m
MilwaukeeSimpson Bay
MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana
MKESXM
Milwaukee-Mitchell
Tue 4/6
5:00 am-1:30 pm
1 stop7h 30m
Simpson Bay Princess Juliana
Tue 4/13
2:30 pm-10:50 pm
1 stop9h 20m
MilwaukeeSimpson Bay
MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana
MKESXM
Milwaukee-Mitchell
Fri 2/19
7:32 pm-4:27 pm
2 stops18h 55m
Simpson Bay Princess Juliana
Fri 2/26
1:27 pm-11:55 pm
1 stop12h 28m
MilwaukeeSimpson Bay
MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana
MKESXM
Milwaukee-Mitchell
Sat 1/30
12:45 pm-3:45 pm
3 stops25h 00m
Simpson Bay Princess Juliana
Fri 2/5
4:20 pm-2:00 pm
3 stops23h 40m
MilwaukeeSimpson Bay
MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana
MKESXM
Milwaukee-Mitchell
Sat 3/20
10:45 am-2:40 pm
3 stops26h 55m
Simpson Bay Princess Juliana
Sat 3/27
2:40 pm-1:43 pm
2 stops24h 03m
See travel insights to Simpson Bay from
How to get the cheapest flight ticket from Milwaukee to Simpson Bay
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest airline that flies from Milwaukee-Mitchell to Simpson Bay Princess Juliana?
Southwest, United Airlines, and American Airlines are the most popular carriers operating from Milwaukee-Mitchell to Simpson Bay Princess Juliana
What airlines fly to Simpson Bay?
American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Simpson Bay from Milwaukee according to our data. American Airlines is the first choice among our users, with 54% of people opting to fly with this airline when traveling to Simpson Bay. Keep in mind that there are 5 different airlines that fly to Simpson Bay on a routine basis, so you have a few additional options to choose from.
Which airport is the most popular layover for flights between Milwaukee and Simpson Bay?
Atlanta (ATL) was the most common stop: 76% of momondo users choosing 1-stop flights on this route connected there.
Which layover airport offers the lowest fares from Milwaukee to Simpson Bay?
Flights via Chicago (ORD) offer the lowest average round-trip price of $521.
Which layover airport has the shortest travel time from Milwaukee to Simpson Bay?
Flights connecting via Chicago (ORD) have the shortest average one-way travel time: 7h 27m.
Which layover airport has the shortest connection time from Milwaukee to Simpson Bay?
Orlando (MCO) has the shortest average layover time for this route: 1h 50m.
When to book flights from Milwaukee to Simpson Bay
Cheap Milwaukee to Simpson Bay (MKE to SXM) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Milwaukee to Simpson Bay
Frequently asked questions about flying from Milwaukee to Simpson Bay
How far is Milwaukee-Mitchell to Simpson Bay Princess Juliana by plane?
The straight-line distance from Milwaukee-Mitchell to Simpson Bay Princess Juliana is 2252.3 mi. A reasonable flight in good conditions will take 7h 10m.
When did momondo last update prices for flights from Milwaukee-Mitchell Airport to Simpson Bay Princess Juliana Airport?
Prices for flights from Milwaukee-Mitchell Airport to Simpson Bay Princess Juliana Airport refresh daily.
How many operators does momondo search for flights from Milwaukee-Mitchell Airport to Simpson Bay Princess Juliana Airport?
There are 4 operators available for flights from Milwaukee-Mitchell Airport to Simpson Bay Princess Juliana Airport as of October 2026.
How old do you have to be to fly from Milwaukee-Mitchell Airport to Simpson Bay Princess Juliana Airport?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Milwaukee-Mitchell Airport to Simpson Bay Princess Juliana Airport.
What documentation or ID do you need to fly to Simpson Bay Princess Juliana Airport?
The travel and health documents required for your trip to Simpson Bay Princess Juliana Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Simpson Bay Princess Juliana Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular airline from Milwaukee to Simpson Bay?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Milwaukee to Simpson Bay is American Airlines (31% of total bookings). The next most popular airlines are Delta (30%), United Airlines (19%), and Southwest (19%).
Best airlines flying from Milwaukee to Simpson Bay
Compare and see reviews for airlines that fly from Milwaukee to Simpson Bay with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $478 | Free Cancellation | Rating 7.4 10,301 reviews | |||
| PriceFrom $483 | Free Cancellation | Rating 7.8 8,633 reviews | |||
| PriceFrom $526 | Free Cancellation | Rating 7.9 4,214 reviews | |||
| PriceFrom $612 | Free Cancellation | Rating 7.0 12,129 reviews |
Traveling to a place near Simpson Bay?
Book flights to Simpson Bay if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Milwaukee to Simpson Bay?
Finding the right flight to Simpson Bay from Milwaukee is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Simpson Bay quick and easy, saving you time and money.
Can I find flights from Milwaukee to Simpson Bay with flexible booking policies on momondo?
Yes. momondo allows you to filter the results for Milwaukee to Simpson Bay flights to just show those with flexible booking policies.
How can momondo help me find flights from Milwaukee to Simpson Bay?
Once all potential Milwaukee to Simpson Bay flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.
I’m not ready to book a flight from Milwaukee to Simpson Bay right now. Can momondo alert me if prices change?
Price alerts on flights to Simpson Bay from Milwaukee are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.