Our data shows that April tends to be the cheapest month to fly to Simpson Bay from Wisconsin. Users have commonly found prices around $827 for the month, but tickets can be as low as $577. Due to multiple factors, prepare for potentially higher prices in June.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Wisconsin to Simpson Bay as you normally would.
Fly from
Fly to
Budget
$242 - $479
Route
Depart
Return
Price
Chicago O'Hare IntlSimpson Bay Princess Juliana
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Tue 5/28
1 stop19h 03m
Simpson Bay Princess Juliana
Sat 6/1
1 stop9h 31m
Chicago O'Hare IntlSimpson Bay Princess Juliana
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Tue 5/28
1 stop18h 04m
Simpson Bay Princess Juliana
Mon 6/3
1 stop9h 45m
Chicago O'Hare IntlSimpson Bay Princess Juliana
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Tue 5/28
2 stops19h 08m
Simpson Bay Princess Juliana
Sat 6/1
1 stop9h 31m
Chicago O'Hare IntlSimpson Bay Princess Juliana
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Fri 5/31
1 stop18h 04m
Simpson Bay Princess Juliana
Mon 6/3
1 stop9h 45m
Chicago O'Hare IntlSimpson Bay Princess Juliana
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Wed 5/29
1 stop7h 44m
Simpson Bay Princess Juliana
Fri 6/7
1 stop11h 11m
Chicago O'Hare IntlSimpson Bay Princess Juliana
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Sat 6/1
2 stops26h 59m
Simpson Bay Princess Juliana
Sat 6/8
1 stop27h 45m
Chicago O'Hare IntlSimpson Bay Princess Juliana
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Sat 6/1
1 stop20h 08m
Simpson Bay Princess Juliana
Mon 6/3
2 stops21h 15m
Milwaukee-MitchellSimpson Bay Princess Juliana
MKE - SXM
MKESXM
Milwaukee-Mitchell
Tue 9/3
2 stops19h 09m
Simpson Bay Princess Juliana
Tue 9/10
2 stops19h 19m
Madison Truax FieldSimpson Bay Princess Juliana
MSN - SXM
MSNSXM
Madison Truax Field
Sun 9/15
2 stops18h 49m
Simpson Bay Princess Juliana
Wed 9/18
2 stops18h 26m
No data available for this route at this time. Please check back soon.
Overall
Crew
Boarding
Comfort
Entertainment
Food
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Overall
Crew
Boarding
Comfort
Entertainment
Food
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Overall
Crew
Boarding
Comfort
Entertainment
Food
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Overall
Crew
Boarding
Comfort
Entertainment
Food
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Overall
Crew
Boarding
Comfort
Entertainment
Food
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Overall
Crew
Boarding
Comfort
Entertainment
Food
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
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