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Cheap flights from Wisconsin to Simpson Bay from $109

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 9/6. 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

Spirit Airlines Logo
8:12 pm - 2:00 pmORD-SXM
16h 48m1 stop
Spirit Airlines Logo
3:05 pm - 10:48 pmSXM-ORD
8h 43m1 stop
$282Spirit Airlines
Find Deal
Tue, Sep 2 - Sat, Sep 6
Spirit Airlines Logo
5:05 am - 2:00 pmORD-SXM
7h 55m1 stop
Spirit Airlines Logo
3:05 pm - 11:59 pmSXM-ORD
9h 54m1 stop
$314Spirit Airlines
Find Deal
Sat, Aug 30 - Wed, Sep 3
Logo
10:27 am - 8:12 amORD-SXM
20h 45m2 stops
Logo
3:05 pm - 10:48 pmSXM-ORD
8h 43m1 stop
$355
Find Deal
Tue, Sep 2 - Sat, Sep 6
Logo
10:27 am - 8:12 amORD-SXM
20h 45m2 stops
Logo
3:05 pm - 5:39 pmSXM-ORD
27h 34m1 stop
$411
Find Deal
Tue, Sep 16 - Fri, Sep 26
Sun Country Air Logo
10:08 am - 5:32 pmMSP-SXM
5h 24mnonstop
Sun Country Air Logo
6:32 pm - 10:51 pmSXM-MSP
6h 19mnonstop
$455Sun Country Air
Find Deal
Sat, Jan 10 - Sat, Jan 17
JetBlue Logo
6:45 am - 4:29 pmORD-SXM
7h 44m1 stop
JetBlue Logo
5:36 pm - 10:45 pmSXM-ORD
31h 09m1 stop
$476JetBlue
Find Deal
Sun, Nov 16 - Wed, Nov 26
JetBlue Logo
7:00 am - 4:29 pmORD-SXM
7h 29m1 stop
JetBlue Logo
6:00 pm - 10:28 amSXM-ORD
18h 28m1 stop
$477JetBlue
Find Deal
Sun, Dec 7 - Sat, Dec 13
Delta Logo
6:00 am - 1:56 pmMKE-SXM
6h 56m1 stop
Delta Logo
3:21 pm - 11:36 pmSXM-MKE
9h 15m1 stop
$497Delta
Find Deal
Sun, Aug 31 - Sun, Sep 7
Sun Country Air Logo
10:08 am - 5:32 pmMSP-SXM
5h 24mnonstop
Sun Country Air Logo
6:32 pm - 10:51 pmSXM-MSP
6h 19mnonstop
$517Sun Country Air
Find Deal
Sat, Jan 17 - Sat, Jan 24
Delta Logo
5:40 am - 1:50 pmMSN-SXM
7h 10m1 stop
Delta Logo
3:20 pm - 10:58 pmSXM-MSN
8h 38m1 stop
$612Delta
Find Deal
Fri, Sep 19 - Fri, Sep 26

Spirit Airlines flights from Wisconsin to Simpson Bay

Our best Spirit Airlines deals on Wisconsin to Simpson Bay flight tickets
Spirit Airlines
Sep 2
ORD8:12 pmChicago O'Hare Intl
16h 48m
1 stop
SXM2:00 pmSimpson Bay Princess Juliana
Sep 6
SXM3:05 pmSimpson Bay Princess Juliana
8h 43m
1 stop
ORD10:48 pmChicago O'Hare Intl
$282
Find similar
Spirit Airlines
Aug 30
ORD5:05 amChicago O'Hare Intl
7h 55m
1 stop
SXM2:00 pmSimpson Bay Princess Juliana
Sep 3
SXM3:05 pmSimpson Bay Princess Juliana
9h 54m
1 stop
ORD11:59 pmChicago O'Hare Intl
$314
Find similar
Spirit Airlines
Sep 8
ORD5:05 amChicago O'Hare Intl
7h 55m
1 stop
SXM2:00 pmSimpson Bay Princess Juliana
Sep 15
SXM3:05 pmSimpson Bay Princess Juliana
8h 43m
1 stop
ORD10:48 pmChicago O'Hare Intl
$337
Find similar

American Airlines flights from Wisconsin to Simpson Bay

Our best American Airlines deals on Wisconsin to Simpson Bay flight tickets
American Airlines
Dec 6
ATW4:47 pmAppleton Intl
20h 53m
2 stops
SXM3:40 pmSimpson Bay Princess Juliana
Dec 11
SXM3:35 pmSimpson Bay Princess Juliana
8h 13m
1 stop
ATW9:48 pmAppleton Intl
$592
Find similar
American Airlines
Dec 6
ATW6:47 amAppleton Intl
29h 08m
1 stop
SXM1:55 pmSimpson Bay Princess Juliana
Dec 11
SXM3:35 pmSimpson Bay Princess Juliana
8h 13m
1 stop
ATW9:48 pmAppleton Intl
$597
Find similar
American Airlines
Sep 27
GRB4:35 pmGreen Bay Austin-Straubel
19h 44m
2 stops
SXM1:19 pmSimpson Bay Princess Juliana
Oct 4
SXM2:20 pmSimpson Bay Princess Juliana
19h 58m
2 stops
GRB9:18 amGreen Bay Austin-Straubel
$617
Find similar

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 August 7, 2025.
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

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 9/2

8:12 pm-2:00 pm

1 stop16h 48m

Simpson Bay Princess Juliana

Sat 9/6

3:05 pm-10:48 pm

1 stop8h 43m

$282

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 8/30

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Wed 9/3

3:05 pm-11:59 pm

1 stop9h 54m

$314

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 9/2

10:27 am-8:12 am

2 stops20h 45m

Simpson Bay Princess Juliana

Sat 9/6

3:05 pm-10:48 pm

1 stop8h 43m

$355

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 9/16

10:27 am-8:12 am

2 stops20h 45m

Simpson Bay Princess Juliana

Fri 9/26

3:05 pm-5:39 pm

1 stop27h 34m

$411

MinneapolisSimpson Bay

MSP - SXM

MSPSXM

Minneapolis St Paul

Sat 1/10

10:08 am-5:32 pm

Nonstop5h 24m

Simpson Bay Princess Juliana

Sat 1/17

6:32 pm-10:51 pm

Nonstop6h 19m

$455

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 11/16

6:45 am-4:29 pm

1 stop7h 44m

Simpson Bay Princess Juliana

Wed 11/26

5:36 pm-10:45 pm

1 stop31h 09m

$476

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 12/7

7:00 am-4:29 pm

1 stop7h 29m

Simpson Bay Princess Juliana

Sat 12/13

6:00 pm-10:28 am

1 stop18h 28m

$477

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sun 8/31

6:00 am-1:56 pm

1 stop6h 56m

Simpson Bay Princess Juliana

Sun 9/7

3:21 pm-11:36 pm

1 stop9h 15m

$497

MinneapolisSimpson Bay

MSP - SXM

MSPSXM

Minneapolis St Paul

Sat 1/17

10:08 am-5:32 pm

Nonstop5h 24m

Simpson Bay Princess Juliana

Sat 1/24

6:32 pm-10:51 pm

Nonstop6h 19m

$517

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Fri 9/19

5:40 am-1:50 pm

1 stop7h 10m

Simpson Bay Princess Juliana

Fri 9/26

3:20 pm-10:58 pm

1 stop8h 38m

$612

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 day to depart on your flight to Simpson Bay?

Our data shows that Tuesday is the least expensive day to fly to Simpson Bay. Tickets to fly out on this day can be as low as $557. Flights from Wisconsin to Simpson Bay on a Monday will generally be more expensive and average around $730. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Simpson Bay?

According to our data, the cheapest time of day to fly to Simpson Bay is in the afternoon. momondo users have found flights departing from Wisconsin to Simpson Bay in the afternoon for as low as $614. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In contrast, the most expensive time of day to depart to Simpson Bay is in the morning when prices are around $669.

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

Best Price Found

$109

Fastest flight time

5h 24m

Direct flights

Mon and Sun

Airports in Simpson Bay

1 airport
The best one-way flight to Simpson Bay from Wisconsin in the past 72 hours is $109. The best round-trip flight deal from Wisconsin to Simpson Bay found on momondo in the last 72 hours is $282.
The fastest flight from Wisconsin to Simpson Bay takes 5h 24m
Direct flights go from Wisconsin to Simpson Bay on Monday and Sunday. Airlines offering direct flights are: United Airlines, Delta and American Airlines.
There is 1 airport near Simpson Bay: Simpson Bay Princess Juliana (SXM)
Search flight deals

  • 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 $504Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $514Free CancellationRating
8.0
7,985 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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