Due to multiple factors, expect to potentially pay more when booking in January. For low rates, November can be a great choice for travel to Illinois. Flights to Illinois from Simpson Bay in November are about $699 on average during November, but can be found for as low as $214.
When flying from Simpson Bay to Illinois, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Fly from
Fly to
Budget
$374 - $896
Route
Depart
Return
Price
Simpson Bay Princess JulianaChicago O'Hare Intl
SXM - ORD
SXMORD
Simpson Bay Princess Juliana
Wed 7/10
1 stop30h 10m
Chicago O'Hare Intl
Wed 7/17
1 stop8h 05m
Simpson Bay Princess JulianaChicago O'Hare Intl
SXM - ORD
SXMORD
Simpson Bay Princess Juliana
Wed 5/29
1 stop9h 45m
Chicago O'Hare Intl
Sun 6/2
1 stop18h 04m
Simpson Bay Princess JulianaChicago O'Hare Intl
SXM - ORD
SXMORD
Simpson Bay Princess Juliana
Wed 7/10
2 stops30h 42m
Chicago O'Hare Intl
Wed 7/17
1 stop8h 05m
Simpson Bay Princess JulianaChicago O'Hare Intl
SXM - ORD
SXMORD
Simpson Bay Princess Juliana
Wed 5/29
1 stop9h 45m
Chicago O'Hare Intl
Sun 6/2
2 stops15h 19m
Simpson Bay Princess JulianaChicago O'Hare Intl
SXM - ORD
SXMORD
Simpson Bay Princess Juliana
Tue 6/25
1 stop22h 19m
Chicago O'Hare Intl
Fri 6/28
1 stop18h 08m
Simpson Bay Princess JulianaChicago O'Hare Intl
SXM - ORD
SXMORD
Simpson Bay Princess Juliana
Wed 7/10
2 stops21h 55m
Chicago O'Hare Intl
Wed 7/17
2 stops50h 41m
Simpson Bay Princess JulianaChicago O'Hare Intl
SXM - ORD
SXMORD
Simpson Bay Princess Juliana
Tue 6/18
1 stop8h 44m
Chicago O'Hare Intl
Sun 6/23
1 stop17h 51m
Simpson Bay Princess JulianaChicago O'Hare Intl
SXM - ORD
SXMORD
Simpson Bay Princess Juliana
Tue 6/25
1 stop8h 10m
Chicago O'Hare Intl
Fri 6/28
2 stops15h 11m
Simpson Bay Princess JulianaChicago O'Hare Intl
SXM - ORD
SXMORD
Simpson Bay Princess Juliana
Tue 6/18
2 stops17h 12m
Chicago O'Hare Intl
Sun 6/23
2 stops17h 25m
No data available for this route at this time. Please check back soon.
Boarding
Overall
Crew
Comfort
Entertainment
Food
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Boarding
Overall
Crew
Comfort
Entertainment
Food
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Boarding
Overall
Crew
Comfort
Entertainment
Food
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Boarding
Overall
Crew
Comfort
Entertainment
Food
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Boarding
Overall
Crew
Comfort
Entertainment
Food
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Boarding
Overall
Crew
Comfort
Entertainment
Food
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
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