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Cheap flights from Wisconsin to Simpson Bay from $71

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Wisconsin to Simpson Bay departing on 4/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Wisconsin to Simpson Bay

Cheap round-trip flights

Enter your travel dates to find the best prices.
Spirit Airlines Logo
7:15 pm - 1:37 pm
ORD
-
SXM
17h 22m
1 stop
Spirit Airlines Logo
2:35 pm - 11:15 pm
SXM
-
ORD
9h 40m
1 stop
$253Spirit Airlines
Sa, Mai 2 - Sa, Mai 9
Spirit Airlines Logo
7:15 pm - 1:37 pm
ORD
-
SXM
17h 22m
1 stop
Spirit Airlines Logo
2:35 pm - 11:15 pm
SXM
-
ORD
9h 40m
1 stop
$254Spirit Airlines
Sa, Apr 25 - Sa, Mai 9
Multiple Airlines Logo
7:15 pm - 1:37 pm
ORD
-
SXM
17h 22m
1 stop
Multiple Airlines Logo
2:35 pm - 11:38 pm
SXM
-
ORD
10h 03m
1 stop
$257Multiple Airlines
Sa, Mai 2 - Do, Mai 7
Air Canada Logo
7:00 am - 5:00 pm
MSP
-
SXM
9h 00m
1 stop
Air Canada Logo
6:00 pm - 12:10 pm
SXM
-
MSP
19h 10m
1 stop
$409Air Canada
Sa, Jun 6 - Sa, Jun 13
Air Canada Logo
7:00 am - 5:00 pm
MSP
-
SXM
9h 00m
1 stop
Air Canada Logo
6:00 pm - 8:40 pm
SXM
-
MSP
51h 40m
2 stops
$422Air Canada
Sa, Jun 6 - Sa, Jun 13
Multiple Airlines Logo
4:30 pm - 1:37 pm
MSP
-
SXM
20h 07m
2 stops
Multiple Airlines Logo
2:35 pm - 11:38 am
SXM
-
MSP
22h 03m
1 stop
$446Multiple Airlines
Sa, Mai 2 - Sa, Mai 9
Delta Logo
6:47 pm - 1:53 pm
MKE
-
SXM
18h 06m
1 stop
Delta Logo
3:18 pm - 11:56 pm
SXM
-
MKE
9h 38m
1 stop
$483Delta
Mi, Jul 1 - Do, Jul 9
Delta Logo
5:45 am - 1:50 pm
MSN
-
SXM
7h 05m
1 stop
Delta Logo
3:20 pm - 10:35 pm
SXM
-
MSN
8h 15m
1 stop
$515Delta
Mi, Sep 16 - Mi, Sep 23
American Airlines Logo
6:31 pm - 1:21 pm
ATW
-
SXM
17h 50m
2 stops
American Airlines Logo
4:35 pm - 10:05 am
SXM
-
ATW
18h 30m
2 stops
$520American Airlines
Sa, Mai 2 - Fr, Mai 8
American Airlines Logo
7:01 am - 1:21 pm
ATW
-
SXM
29h 20m
1 stop
American Airlines Logo
4:35 pm - 12:50 pm
SXM
-
ATW
21h 15m
2 stops
$529American Airlines
Sa, Mai 2 - Fr, Mai 8

Air Canada flights from Wisconsin to Simpson Bay

Our best Air Canada deals on Wisconsin to Simpson Bay flight tickets
Air Canada
Jun 13
ORD7:09 amChicago O'Hare Intl
8h 51m
1 stop
SXM5:00 pmSimpson Bay Princess Juliana
Jun 20
SXM6:00 pmSimpson Bay Princess Juliana
14h 45m
2 stops
ORD7:45 amChicago O'Hare Intl
$359
Air Canada
Jun 13
ORD7:09 amChicago O'Hare Intl
8h 51m
1 stop
SXM5:00 pmSimpson Bay Princess Juliana
Jun 20
SXM6:00 pmSimpson Bay Princess Juliana
20h 22m
1 stop
ORD1:22 pmChicago O'Hare Intl
$379
Air Canada
Jun 20
ORD7:09 amChicago O'Hare Intl
8h 51m
1 stop
SXM5:00 pmSimpson Bay Princess Juliana
Jun 27
SXM6:00 pmSimpson Bay Princess Juliana
21h 55m
1 stop
ORD2:55 pmChicago O'Hare Intl
$380

American Airlines flights from Wisconsin to Simpson Bay

Our best American Airlines deals on Wisconsin to Simpson Bay flight tickets
American Airlines
May 2
ATW6:31 pmAppleton Intl
17h 50m
2 stops
SXM1:21 pmSimpson Bay Princess Juliana
May 8
SXM4:35 pmSimpson Bay Princess Juliana
18h 30m
2 stops
ATW10:05 amAppleton Intl
$520
American Airlines
May 2
ATW7:01 amAppleton Intl
29h 20m
1 stop
SXM1:21 pmSimpson Bay Princess Juliana
May 8
SXM4:35 pmSimpson Bay Princess Juliana
21h 15m
2 stops
ATW12:50 pmAppleton Intl
$529
American Airlines
Sep 16
MSN1:58 pmMadison Truax Field
22h 17m
2 stops
SXM1:15 pmSimpson Bay Princess Juliana
Sep 23
SXM2:50 pmSimpson Bay Princess Juliana
19h 12m
2 stops
MSN9:02 amMadison Truax Field
$560

momondo Fare Finder

 
Customize your flight search to find flights from Wisconsin to Simpson Bay that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated April 11, 2026.
Use the filters below to find and compare flights from Wisconsin to Simpson Bay that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sa 5/2

7:15 pm-1:37 pm

1 stop17h 22m

Simpson Bay Princess Juliana

Sa 5/9

2:35 pm-11:15 pm

1 stop9h 40m

$253

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sa 4/25

7:15 pm-1:37 pm

1 stop17h 22m

Simpson Bay Princess Juliana

Sa 5/9

2:35 pm-11:15 pm

1 stop9h 40m

$254

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sa 5/2

7:15 pm-1:37 pm

1 stop17h 22m

Simpson Bay Princess Juliana

Do 5/7

2:35 pm-11:38 pm

1 stop10h 03m

$257

MinneapolisSimpson Bay

MSP - SXM

MSPSXM

Minneapolis St Paul

Sa 6/6

7:00 am-5:00 pm

1 stop9h 00m

Simpson Bay Princess Juliana

Sa 6/13

6:00 pm-12:10 pm

1 stop19h 10m

$409

MinneapolisSimpson Bay

MSP - SXM

MSPSXM

Minneapolis St Paul

Sa 6/6

7:00 am-5:00 pm

1 stop9h 00m

Simpson Bay Princess Juliana

Sa 6/13

6:00 pm-8:40 pm

2 stops51h 40m

$422

MinneapolisSimpson Bay

MSP - SXM

MSPSXM

Minneapolis St Paul

Sa 5/2

4:30 pm-1:37 pm

2 stops20h 07m

Simpson Bay Princess Juliana

Sa 5/9

2:35 pm-11:38 am

1 stop22h 03m

$446

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Mi 7/1

6:47 pm-1:53 pm

1 stop18h 06m

Simpson Bay Princess Juliana

Do 7/9

3:18 pm-11:56 pm

1 stop9h 38m

$483
Quickest round-trip

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Mi 9/16

5:45 am-1:50 pm

1 stop7h 05m

Simpson Bay Princess Juliana

Mi 9/23

3:20 pm-10:35 pm

1 stop8h 15m

$515

AppletonSimpson Bay

ATW - SXM

ATWSXM

Appleton Intl

Sa 5/2

6:31 pm-1:21 pm

2 stops17h 50m

Simpson Bay Princess Juliana

Fr 5/8

4:35 pm-10:05 am

2 stops18h 30m

$520

AppletonSimpson Bay

ATW - SXM

ATWSXM

Appleton Intl

Sa 5/2

7:01 am-1:21 pm

1 stop29h 20m

Simpson Bay Princess Juliana

Fr 5/8

4:35 pm-12:50 pm

2 stops21h 15m

$529

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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2

See travel insights to Simpson Bay from

How to get the cheapest flight ticket from Wisconsin 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 Wisconsin to Simpson Bay Princess Juliana?

Spirit Airlines, Delta, and American Airlines are the most popular carriers operating from Wisconsin to Simpson Bay Princess Juliana

Cheap Wisconsin to Simpson Bay flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Wisconsin to Simpson Bay

Fastest flight time

5h 12m

Direct flights

Sun

Airports in Simpson Bay

1 airport
The fastest flight from Wisconsin to Simpson Bay takes 5h 12m
Direct flights go from Wisconsin to Simpson Bay on Sunday. There are no airlines offering direct flights.
There is 1 airport in Simpson Bay. From Wisconsin there are direct flights to Simpson Bay Princess Juliana (SXM).
Search flight deals

Frequently asked questions about flying from Wisconsin to Simpson Bay

  • When did momondo last update prices for flights from Wisconsin to Simpson Bay Princess Juliana Airport?

    Prices for flights from Wisconsin to Simpson Bay Princess Juliana Airport were last updated today.

  • How many operators does momondo search for flights from Wisconsin to Simpson Bay Princess Juliana Airport?

  • How old do you have to be to fly from Wisconsin to Simpson Bay Princess Juliana Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Wisconsin 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 you'll need for your trip to Simpson Bay Princess Juliana Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Simpson Bay Princess Juliana Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Best airlines flying from Wisconsin to Simpson Bay

Compare and see reviews for airlines that fly from Wisconsin to Simpson Bay with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $605Free CancellationRating
7.1
11,572 reviews
Search American Airlines flights
DeltaPriceFrom $609Free CancellationRating
7.9
8,406 reviews
Search Delta flights

Traveling to a place near Simpson Bay?

Book flights to Simpson Bay if you plan to visit one of these locations
Philipsburg

Why use momondo?

Why should I use momondo to find a flight deal from Wisconsin to Simpson Bay?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Wisconsin to Simpson Bay. momondo saves you time and could save you money on your trip.

Can I find flights from Wisconsin to Simpson Bay with flexible booking policies on momondo?

Flights from Wisconsin to Simpson Bay with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Wisconsin to Simpson Bay?

momondo helps you find the best flight between Wisconsin and Simpson Bay by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Wisconsin to Simpson Bay right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Wisconsin to Simpson Bay now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Simpson Bay and let you know when they change.

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Airlines are sorted and displayed according to clicks in the past 7 days on momondo
American Airlines
Delta