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Cheap flights from Wisconsin to Simpson Bay from $113

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 12/17. 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
5:00 am - 2:15 pmORD-SXM
7h 15m1 stop
Spirit Airlines Logo
3:20 pm - 12:30 amSXM-ORD
11h 10m1 stop
$309Spirit Airlines
Find Deal
Wed, Dec 17 - Wed, Dec 24
Spirit Airlines Logo
5:00 am - 2:15 pmORD-SXM
7h 15m1 stop
Spirit Airlines Logo
3:20 pm - 12:09 amSXM-ORD
10h 49m1 stop
$310Spirit Airlines
Find Deal
Sat, Dec 13 - Wed, Dec 17
Multiple Airlines Logo
6:15 am - 2:15 pmORD-SXM
30h 00m1 stop
Multiple Airlines Logo
3:20 pm - 12:09 amSXM-ORD
10h 49m1 stop
$337Multiple Airlines
Find Deal
Thu, Dec 11 - Wed, Dec 17
Multiple Airlines Logo
5:05 am - 3:20 pmORD-SXM
8h 15m1 stop
Multiple Airlines Logo
3:09 pm - 12:18 amSXM-ORD
11h 09m1 stop
$345Multiple Airlines
Find Deal
Sat, Jan 31 - Sat, Feb 7
Frontier Logo
5:05 am - 3:20 pmORD-SXM
8h 15m1 stop
Frontier Logo
4:30 pm - 11:35 pmSXM-ORD
9h 05m1 stop
$363Frontier
Find Deal
Sat, Feb 7 - Sat, Feb 14
Delta Logo
5:23 am - 2:55 pmORD-SXM
7h 32m1 stop
Delta Logo
3:53 pm - 10:43 pmSXM-ORD
8h 50m1 stop
$375Delta
Find Deal
Fri, Nov 28 - Wed, Dec 3
American Airlines Logo
7:30 pm - 12:58 pmORD-SXM
15h 28m1 stop
American Airlines Logo
3:09 pm - 11:27 pmSXM-ORD
10h 18m1 stop
$381American Airlines
Find Deal
Wed, Jan 7 - Wed, Jan 14
American Airlines Logo
8:56 pm - 1:45 pmORD-SXM
14h 49m2 stops
American Airlines Logo
1:41 pm - 9:21 pmSXM-ORD
9h 40m1 stop
$386American Airlines
Find Deal
Mon, Feb 9 - Wed, Feb 18
Frontier Logo
5:05 am - 3:20 pmORD-SXM
8h 15m1 stop
Frontier Logo
4:30 pm - 12:12 amSXM-ORD
9h 42m1 stop
$395Frontier
Find Deal
Sat, Jan 10 - Sat, Jan 17
Delta Logo
5:30 am - 2:09 pmGRB-SXM
7h 39m1 stop
Delta Logo
1:50 pm - 9:58 pmSXM-GRB
9h 08m1 stop
$605Delta
Find Deal
Sun, Apr 26 - Thu, Apr 30

Spirit Airlines flights from Wisconsin to Simpson Bay

Our best Spirit Airlines deals on Wisconsin to Simpson Bay flight tickets
Spirit Airlines
Dec 17
ORD5:00 amChicago O'Hare Intl
7h 15m
1 stop
SXM2:15 pmSimpson Bay Princess Juliana
Dec 24
SXM3:20 pmSimpson Bay Princess Juliana
11h 10m
1 stop
ORD12:30 amChicago O'Hare Intl
$309
Find similar
Spirit Airlines
Dec 13
ORD5:00 amChicago O'Hare Intl
7h 15m
1 stop
SXM2:15 pmSimpson Bay Princess Juliana
Dec 17
SXM3:20 pmSimpson Bay Princess Juliana
10h 49m
1 stop
ORD12:09 amChicago O'Hare Intl
$310
Find similar
Spirit Airlines
Jan 28
ORD5:05 amChicago O'Hare Intl
8h 05m
1 stop
SXM3:10 pmSimpson Bay Princess Juliana
Feb 6
SXM4:28 pmSimpson Bay Princess Juliana
9h 14m
1 stop
ORD11:42 pmChicago O'Hare Intl
$313
Find similar

Frontier flights from Wisconsin to Simpson Bay

Our best Frontier deals on Wisconsin to Simpson Bay flight tickets
Frontier
Feb 7
ORD5:05 amChicago O'Hare Intl
8h 15m
1 stop
SXM3:20 pmSimpson Bay Princess Juliana
Feb 14
SXM4:30 pmSimpson Bay Princess Juliana
9h 05m
1 stop
ORD11:35 pmChicago O'Hare Intl
$363
Find similar
Frontier
Jan 10
ORD5:05 amChicago O'Hare Intl
8h 15m
1 stop
SXM3:20 pmSimpson Bay Princess Juliana
Jan 17
SXM4:30 pmSimpson Bay Princess Juliana
9h 42m
1 stop
ORD12:12 amChicago O'Hare Intl
$395
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 November 6, 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

Wed 12/17

5:00 am-2:15 pm

1 stop7h 15m

Simpson Bay Princess Juliana

Wed 12/24

3:20 pm-12:30 am

1 stop11h 10m

$309

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 12/13

5:00 am-2:15 pm

1 stop7h 15m

Simpson Bay Princess Juliana

Wed 12/17

3:20 pm-12:09 am

1 stop10h 49m

$310

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 12/11

6:15 am-2:15 pm

1 stop30h 00m

Simpson Bay Princess Juliana

Wed 12/17

3:20 pm-12:09 am

1 stop10h 49m

$337

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 1/31

5:05 am-3:20 pm

1 stop8h 15m

Simpson Bay Princess Juliana

Sat 2/7

3:09 pm-12:18 am

1 stop11h 09m

$345

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 2/7

5:05 am-3:20 pm

1 stop8h 15m

Simpson Bay Princess Juliana

Sat 2/14

4:30 pm-11:35 pm

1 stop9h 05m

$363

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 11/28

5:23 am-2:55 pm

1 stop7h 32m

Simpson Bay Princess Juliana

Wed 12/3

3:53 pm-10:43 pm

1 stop8h 50m

$375

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 1/7

7:30 pm-12:58 pm

1 stop15h 28m

Simpson Bay Princess Juliana

Wed 1/14

3:09 pm-11:27 pm

1 stop10h 18m

$381

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 2/9

8:56 pm-1:45 pm

2 stops14h 49m

Simpson Bay Princess Juliana

Wed 2/18

1:41 pm-9:21 pm

1 stop9h 40m

$386

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 1/10

5:05 am-3:20 pm

1 stop8h 15m

Simpson Bay Princess Juliana

Sat 1/17

4:30 pm-12:12 am

1 stop9h 42m

$395

Green BaySimpson Bay

GRB - SXM

GRBSXM

Green Bay Austin-Straubel

Sun 4/26

5:30 am-2:09 pm

1 stop7h 39m

Simpson Bay Princess Juliana

Thu 4/30

1:50 pm-9:58 pm

1 stop9h 08m

$605

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

Fastest flight time

4h 45m

Direct flights

Mon and Sun

Airports in Simpson Bay

1 airport
The fastest flight from Wisconsin to Simpson Bay takes 4h 45m
Direct flights go from Wisconsin to Simpson Bay on Monday and Sunday. There are no airlines offering direct flights.
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
DeltaPriceFrom $584Free CancellationRating
7.9
8,001 reviews
Search Delta flights
American AirlinesPriceFrom $605Free CancellationRating
7.2
11,040 reviews
Search American Airlines 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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