Find Cheap Flights from Chicago O'Hare International to Simpson Bay Princess Juliana (ORD - SXM)

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Fri 12/15
Fri 12/22
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Good to Know

Low Season:
January
Best time to beat the crowds
1%
expected price decrease
High Season:
July
Most popular time to fly
1%
expected price increase
Average Price:
$1431
(avg. price over the last 2 weeks)
Good Deal:
$1155
or less (round trip)

When to Book Flights from Chicago O'Hare International to Simpson Bay Princess Juliana

Average price per month
Flight prices as travel date approaches
-1 day
-2 days

Top tips for Finding a Cheap Flight

Looking for a cheap flight? 25% of our users found flights on this route for $1154 or less.
The cheapest flight from Chicago O'Hare International to Simpson Bay Princess Juliana was found 90 days before departure, on average.
Book at least 3 weeks before departure in order to get a below-average price.
High season is considered to be June, July and August. The cheapest month to fly is January.
Morning departure is around 26% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for Booking Chicago O'Hare International to Simpson Bay Princess Juliana Flights

How long does a flight from Chicago O'Hare International to Simpson Bay Princess Juliana take?
An average nonstop flight takes 6h 55m, covering a distance of 2205 miles.
Which airlines provide the cheapest flights from Chicago O'Hare International to Simpson Bay Princess Juliana?
In the past 3 days, the cheapest round-trip tickets were found on Multiple Airlines ($501), Delta ($526) and American Airlines ($662).
Do I need a passport to fly between Chicago O'Hare International and Simpson Bay Princess Juliana?
Yes.

Book cheap flights from Chicago O'Hare International to Simpson Bay Princess Juliana (round-trip)

Airports
Origin
Chicago
$501
only
$501
Destination
Simpson Bay
$501
only
$501
Sun, Mar 4
ORD
SXM
17h 30m
Wed, Mar 14
SXM
ORD
9h 29m
Trip: 10 days
Overall 0.0 Poor
Based on 0 reviews
Sun, Feb 4
ORD
SXM
6h 55m
Sat, Feb 10
SXM
ORD
9h 44m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14235 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SLC
SNA
Excellent 8.0

Comfortable seats in coach Good snacks Friendly crew

Nothing

MSP
YXE
Excellent 9.3

I was traveling for medical reasons and the Delta crew took great care of me, made sure I was at my connecting gate on time, and even put me in a better seat on the plane. Not sure if that was a coincidental upgrade, or intentional, but it was perfect.

ZAG
CDG
Good 6.0

Old plane, bad food & old crew

SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

ATL
DFW
Excellent 10.0

My entire flight experience was delightful. Was dry impressed with the staff both at Hartsfield-Jackson and DFW...and our flight crew was positively sublime.

Sat, Jun 9
ORD
SXM
17h 40m
Sat, Jun 16
SXM
ORD
8h 48m
Trip: 8 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 26019 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
JFK
MIA
Excellent 8.8

Almost everything. Only the food was lacking. I like their new planes. The outlet at the seat in coach. The magazine options at the seat as well. I did not look at the entertainment so I will not rate that. The crew was professional.

Just the food options. Ginger snaps was what was served for food and a beverage. I suppose this is what obtains on most airlines these days but can't I hope for something more like maybe a sandwich? AA has the opportunity to set themselves apart in this area.

GIG
JFK
Okay 4.6

Nice crew

I booked a LATAM flight for a 10.5 hour flight specifically because they have better in flight entertainment. I arrived at the airport and found it it was operated by AA. 10.5 hours with zero in flight entertainment. HORRIBLE EXPERIENCE.

TUS
PHX
Mediocre 2.0

Nothing.

Everything.

AUS
CLT
Excellent 10.0

My Mom was very grateful for the friendly assistance as she is wheelchair bound and was flying aline. Excellent service!!

Nothing.

DFW
LAX
Excellent 8.3

I liked the expediency of being rescheduled for another flight and the kindness of the American Airlines staff. When I first received my boarding pass, the pass listed gate A24 as the one where my flight was scheduled to depart. The plane destined to depart from Dallas to LAX did not show up. However, a few of us were kindly offered a cot and blankets to sleep on. The next morning I folded the cot and the blankets and found an American Airline staff member who swiftly rescheduled me for another flight to LAX. She did state that the original flight had departed at 11:15 p.m.

From around 6 P.M., December 11, 2017, I was at gate A24 - the gate listed as the Departure gate for my return flight to Los Angeles. The last flight that left went to Saint Louis, I believe. There was never a flight to depart from Gate 24 to Los Angeles. I believe the gate may have been changed and for some reason, those who were at Gate 24 were not informed. Also, the travel instructions on the advertisement for scheduling the flight mentioned the ability to carry on luggage for no additional charge. When I received my boarding pass, it stated I was only allowed to carry on baggage that would fit underneath the seat and not in the overhead bin. I had to pay to check my baggage that I thought was free. In spite of the changes, the flight was a good flight. Thank you

Sat, Apr 14
ORD
SXM
16h 31m
Sat, Apr 21
SXM
ORD
10h 09m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Mon, Jan 15
ORD
SXM
21h 04m
Fri, Jan 26
SXM
ORD
9h 45m
Trip: 12 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Mar 27
ORD
SXM
17h 30m
Mon, Apr 2
SXM
ORD
18h 29m
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
Sat, Feb 10
ORD
SXM
17h 22m
Sat, Feb 24
SXM
ORD
13h 23m
Trip: 15 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Dec 28
ORD
SXM
15h 35m
Tue, Jan 2
SXM
ORD
22h 28m
$1057
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
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The fares displayed include all taxes and fees for economy class travel and were found by the provider in the last 72 hours. Seats are limited and may not be available on all flights and days. Fares are subject to change and may not be available on all flights or dates of travel. Some carriers charge additional fees for extra checked bags. Please check the carriers' sites.