
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $210 (Travelocity) |
One-way from | $61 (Kiwi.com) |
Popular in | December |
Cheapest in | January |
Average price | $600 |
Good round-trip deal | $612 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSimpson Bay
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Wed 3/4
6:04 pm-2:40 pm
2 stops18h 36m
Simpson Bay Princess Juliana
Wed 3/11
2:20 pm-11:47 pm
1 stop10h 27m
ChicagoSimpson Bay
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Thu 2/26
5:15 am-2:15 pm
1 stop7h 00m
Simpson Bay Princess Juliana
Mon 3/2
3:20 pm-11:47 pm
1 stop10h 27m
ChicagoSimpson Bay
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Wed 2/18
12:44 pm-2:15 pm
2 stops23h 31m
Simpson Bay Princess Juliana
Wed 2/25
3:20 pm-11:47 pm
1 stop10h 27m
ChicagoSimpson Bay
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Wed 4/15
1:35 pm-1:16 pm
2 stops22h 41m
Simpson Bay Princess Juliana
Mon 4/20
2:11 pm-11:27 am
1 stop22h 16m
ChicagoSimpson Bay
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Fri 2/20
8:59 am-2:15 pm
2 stops27h 16m
Simpson Bay Princess Juliana
Tue 2/24
3:20 pm-7:11 pm
1 stop29h 51m
ChicagoSimpson Bay
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Wed 3/25
7:15 am-1:40 pm
1 stop29h 25m
Simpson Bay Princess Juliana
Fri 4/3
4:00 pm-1:05 pm
1 stop22h 05m
ChicagoSimpson Bay
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Sat 2/28
9:18 am-2:15 pm
3 stops26h 57m
Simpson Bay Princess Juliana
Sat 3/7
3:20 pm-11:47 pm
1 stop10h 27m
ChicagoSimpson Bay
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Sat 3/7
6:51 pm-10:25 am
2 stops13h 34m
Simpson Bay Princess Juliana
Sat 3/14
2:20 pm-11:17 pm
1 stop9h 57m
ChicagoSimpson Bay
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Sun 3/15
5:05 am-1:15 pm
1 stop7h 10m
Simpson Bay Princess Juliana
Sun 3/22
2:20 pm-5:15 pm
1 stop27h 55m
ChicagoSimpson Bay
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Wed 3/25
5:05 am-1:15 pm
1 stop7h 10m
Simpson Bay Princess Juliana
Wed 4/1
2:35 pm-11:17 pm
1 stop9h 42m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*2 stars |
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 9 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Currently, February is the cheapest month in which you can book a flight from Chicago to Simpson Bay (average of $231). Flying from Chicago to Simpson Bay in June is currently the most expensive (average of $595). 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.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Simpson Bay as you normally would.
About 32% of weekly flights between Chicago and Simpson Bay have experienced delays in the past year, with the average delay time being 97 minutes.
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.
Saturday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Over the last year, American Airlines have had the lowest number of delays on this route, with just 20% of flights being delayed.
Entertainment
Boarding
Crew
Overall
Comfort
Food
Reviews
Jim,Nov 2025
AVL - ATL
Entertainment
Boarding
Crew
Overall
Comfort
Food
Reviews
Jim,Nov 2025
AVL - ATL
Entertainment
Boarding
Crew
Overall
Comfort
Food
Reviews
Jim,Nov 2025
AVL - ATL
Entertainment
Boarding
Crew
Overall
Comfort
Food
Reviews
Jim,Nov 2025
AVL - ATL
Entertainment
Boarding
Crew
Overall
Comfort
Food
Reviews
Jim,Nov 2025
AVL - ATL
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$258 | Average$396 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$290 | Average$522 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$410 | Average$756 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$501 | Average$682 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$568 | Average$731 | FlexibilityNo cancel fee | On-time62% |