Round-trip from | $357 (Cheapflightsfares) |
---|---|
One-way from | $156 (Booking.com) |
Popular in | March |
Cheapest in | September |
Average price | $695 |
Good round-trip deal | $707 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSimpson Bay
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Wed 8/13
5:05 am-2:00 pm
1 stop7h 55m
Simpson Bay Princess Juliana
Wed 8/20
3:05 pm-11:59 pm
1 stop9h 54m
ChicagoSimpson Bay
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Sat 7/19
5:01 am-5:21 pm
2 stops11h 20m
Simpson Bay Princess Juliana
Sat 8/2
3:05 pm-11:53 pm
1 stop9h 48m
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Thu 7/31
9:12 pm-2:00 pm
2 stops15h 48m
Simpson Bay Princess Juliana
Thu 8/7
2:10 pm-8:45 am
1 stop19h 35m
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Mon 8/18
6:04 am-1:56 pm
1 stop6h 52m
Simpson Bay Princess Juliana
Wed 8/27
3:10 pm-12:28 pm
2 stops22h 18m
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Wed 12/10
2:00 pm-3:17 pm
2 stops23h 17m
Simpson Bay Princess Juliana
Mon 12/15
4:10 pm-1:09 pm
2 stops22h 59m
ChicagoSimpson Bay
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Sat 8/2
5:05 am-2:00 pm
1 stop7h 55m
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Sat 8/2
9:12 pm-5:21 pm
2 stops43h 09m
ChicagoSimpson Bay
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Sat 8/2
6:02 pm-7:30 pm
3 stops24h 28m
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Mon 9/8
6:00 am-1:45 pm
1 stop6h 45m
ChicagoSimpson Bay
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Wed 9/10
5:45 am-1:45 pm
1 stop7h 00m
The price you pay for your flight from Chicago to Simpson Bay may vary depending on when you book. For the best chance of a lower fare, look to book 88 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Currently, September is the cheapest month in which you can book a flight from Chicago to Simpson Bay (average of $459). Flying from Chicago to Simpson Bay in March is currently the most expensive (average of $656). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
When flying from Chicago to Simpson Bay, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 54% versus a flight in the morning.
Comfort
Entertainment
Boarding
Food
Overall
Crew
Reviews
Kim,May 2025
PIH - SLC
Comfort
Entertainment
Boarding
Food
Overall
Crew
Reviews
Kim,May 2025
PIH - SLC
Comfort
Entertainment
Boarding
Food
Overall
Crew
Reviews
Kim,May 2025
PIH - SLC
Comfort
Entertainment
Boarding
Food
Overall
Crew
Reviews
Kim,May 2025
PIH - SLC
Comfort
Entertainment
Boarding
Food
Overall
Crew
Reviews
Kim,May 2025
PIH - SLC
Comfort
Entertainment
Boarding
Food
Overall
Crew
Reviews
Kim,May 2025
PIH - SLC
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Cheapest$330 | Average$400 | FlexibilityNo cancel fee | On-time65% | |
Cheapest$564 | Average$722 | FlexibilityNo cancel fee | On-timeN/A | |
Cheapest$614 | Average$708 | FlexibilityNo cancel fee | On-time71% | |
Cheapest$654 | Average$895 | FlexibilityNo cancel fee | On-time69% |