Find Cheap Flights from Chicago to Simpson Bay Princess Juliana (CHI - SXM)

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Good to Know

Low Season:
January
Best time to beat the crowds
3%
expected price decrease
High Season:
July
Most popular time to fly
6%
expected price increase
Average Price:
$592
(avg. price over the last 2 weeks)
Good Deal:
$508
or less (round trip)

When to Book Flights from Chicago 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 $508 or less.
The cheapest flight from Chicago to Simpson Bay Princess Juliana was found 81 days before departure, on average.
Book at least 2 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 3% 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 to Simpson Bay Princess Juliana Flights

How long does a flight from Chicago to Simpson Bay Princess Juliana take?
An average nonstop flight takes 6h 48m, covering a distance of 2190 miles.
Which airlines provide the cheapest flights from Chicago to Simpson Bay Princess Juliana?
In the past 3 days, the cheapest round-trip tickets were found on Spirit Airlines ($423), Multiple Airlines ($505) and American Airlines ($525).
Do I need a passport to fly between Chicago and Simpson Bay Princess Juliana?
Yes.

Book cheap flights from Chicago to Simpson Bay Princess Juliana (round-trip)

Airports
Origin
Chicago
$423
only
$423
$527
only
$527
Destination
Simpson Bay
$423
only
$423
Sat, May 12
ORD
SXM
7h 38m
Sat, May 19
SXM
ORD
10h 09m
Trip: 8 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 52901 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
EWR
IAH
Excellent 8.0

Spirit has gotten better with their customer service. Via email, not by phone.

The flight options need to better

LAX
ORD
Good 7.6

Great last minute price for trip to Chicago

Seats were a bit uncomfortable

IAH
TPA
Okay 4.3

Price Get what you pay

Late flight Indifferent flight attendants

LGA
DTW
Good 6.0

Not a fan of spirit airlines. I would have rather paid an extra few dollars on flight cost for free water then have to be bothered paying on plane

DEN
ORD
Excellent 8.0

Good thing I travel light! I thought the round trip fare was great!

Seating was cramped and seat back did not move

Sun, Apr 8
ORD
SXM
6h 55m
Sat, May 5
SXM
ORD
10h 09m
Trip: 28 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Aug 30
ORD
SXM
6h 48m
Mon, Sep 3
SXM
ORD
12h 20m
Trip: 5 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 28416 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
JFK
MAD
Okay 4.0

Very old plane. No personal entertainment. Very basic service.

PHL
MSY
Good 6.3

Seats were nice, service came pretty quickly considering the size of the plane, boarding went reasonably quick

Started boarding and didn't announce another delay till we're on the aircraft, sitting in the gate for an hour and a half. My audio jack was broken and regardless, it will still trying to charge me for everything even though i was force to be squashed between two people who are also frustrated about sitting doing nothing.

HKG
BKK
Good 6.0

Flight delayed by 35 minutes

LAX
MIA
Mediocre 2.0

Couldn’t sleep because the AC wasnt working. Most miserable flight my life

The AC wasn’t working it was the most miserable flight ever

PHL
AMS
Okay 4.6

Fo

Wed, Apr 4
MDW
SXM
6h 55m
Tue, Apr 10
SXM
MDW
8h 45m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

JFK
CDG
Excellent 10.0

The food and the service

ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

Sun, Aug 12
MDW
SXM
6h 53m
Tue, Aug 14
SXM
MDW
9h 00m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

FLL
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

JFK
MCO
Excellent 8.0

Entertainment system great. Individual choices include recent movies. On board staff very nice

We had issues with baggage. Delta was supposed to transfer 4 bags to Disney for Magic Express transportation. Only 3 went. Disney tried hard to fix problem, and even gave us something to ameliorate the situation. Delta took hard line, wasn't helpful and gave nothing. It took 2 days to find bag.

LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

JFK
CDG
Excellent 10.0

The food and the service

Wed, Apr 18
ORD
SXM
7h 49m
Thu, Apr 26
SXM
ORD
10h 53m
Trip: 9 days
Overall 0.0 Poor
Based on 0 reviews
Mon, Mar 26
ORD
SXM
22h 30m
Wed, Apr 4
SXM
ORD
20h 17m
Trip: 10 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
SLC
YYZ
Excellent 8.0

was a difficult transition from delta to west jet in Toronto and we almost missed the flight

FLL
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

JFK
MCO
Excellent 8.0

Entertainment system great. Individual choices include recent movies. On board staff very nice

We had issues with baggage. Delta was supposed to transfer 4 bags to Disney for Magic Express transportation. Only 3 went. Disney tried hard to fix problem, and even gave us something to ameliorate the situation. Delta took hard line, wasn't helpful and gave nothing. It took 2 days to find bag.

Sat, Mar 3
ORD
SXM
20h 46m
Sat, Mar 10
SXM
ORD
13h 41m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Sun, Feb 25
ORD
SXM
24h 53m
Mon, Mar 5
SXM
ORD
13h 26m
Trip: 9 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Mar 22
ORD
SXM
17h 04m
Fri, Mar 30
SXM
ORD
11h 45m
$1004
Trip: 9 days
Overall 0.0 Poor
Based on 0 reviews
Sun, Mar 25
MDW
SXM
6h 55m
Fri, Mar 30
SXM
MDW
10h 10m
$1588
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
FLL
BOS
Good 6.3

Food and nice crew

No tvs and bad WiFi

SLC
YYZ
Excellent 8.0

was a difficult transition from delta to west jet in Toronto and we almost missed the flight

JFK
MCO
Excellent 8.0

Entertainment system great. Individual choices include recent movies. On board staff very nice

We had issues with baggage. Delta was supposed to transfer 4 bags to Disney for Magic Express transportation. Only 3 went. Disney tried hard to fix problem, and even gave us something to ameliorate the situation. Delta took hard line, wasn't helpful and gave nothing. It took 2 days to find bag.

MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

Show more results

Chicago to Simpson Bay Princess Juliana Flight Information

Flights Arrive in Simpson Bay Princess Juliana
Flights Depart from Chicago
Flight Price $423
Distance 2190 miles
Airlines Spirit Airlines, American Airlines, Delta
*
Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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.