Find cheap flights from Illinois to Sint Maarten

Find cheap flights from Illinois to Sint Maarten

Round-trip
Economy
New York (NYC)
Sint Maarten
Thu 2/27
Thu 3/5
Any month
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Book cheap flights from Illinois to Sint Maarten (round-trip)

Airports
Origin
Chicago
$384
only
$384
Destination
Simpson Bay
$384
only
$384
Sat, Apr 25
ORD
Chicago O'Hare Intl
SXM
Simpson Bay Princess Juliana
7h 33m
Sat, May 2
SXM
Simpson Bay Princess Juliana
ORD
Chicago O'Hare Intl
10h 29m
Trip: 8 days
5.8Okay Show reviews
Overall 5.8 Okay
Based on 60,736 reviews
Overall
5.8
Boarding
6.2
Comfort
5.4
Crew
6.5
Entertainment
4.6
Food
4.8
TPA
ATL
Excellent 10.0

Pros: Flight on time, smooth landing, nice and helpful crew.

MYR
LGA
Good 6.0

Pros: Crew was fine

Cons: Not be delayed 4 hours

TPA
CMH
Mediocre 3.6

Cons: They will hound you to spend more and treat you like cattle.

DTW
FLL
Excellent 10.0

Pros: Brand new plane! Welcoming and friendly flight attendants.

Cons: Offer a free beverage!

BOS
SJU
Mediocre 3.0

Cons: 1 hour delay with minimal explanation, no water for hand washing in bathrooms, tea and coffee not available, not standard weight requirements for checked luggage. These are all significant inconveniences.

Tue, Aug 4
ORD
Chicago O'Hare Intl
SXM
Simpson Bay Princess Juliana
6h 57m
Tue, Aug 11
SXM
Simpson Bay Princess Juliana
ORD
Chicago O'Hare Intl
11h 29m
Trip: 8 days
8.2Excellent Show reviews
Overall 8.2 Excellent
Based on 18,973 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
7.9
Food
7.8
LGA
FLL
Mediocre 2.0

Cons: JetBlue is awful. TVs don’t work. Staff isn’t friendly

BUR
JFK
Okay 4.4

Pros: The plane flew me safely to my destination. Nothing unpleasant happened. Those are the best things I could say about it.

Cons: Overhead bin space was full when I boarded (I was in row 9!), so I had to check my roll aboard and hold my backpack at my feet the whole flight. The bin space above my row was being used to store trays of snacks for the food service. Don't they have somewhere else to store service items so bin space is available for passengers? In explicably we left sunny and calm Burbank 45 minutes late. No water was offered until we'd been on the plane for 2 hours.

POS
FLL
Excellent 10.0

Pros: Vegetarian meal was delicious

Cons: Would be great if WiFi was available

JFK
BQN
Excellent 10.0

Pros: Very smooth flight on time

ATL
BOS
Okay 5.3

Cons: Boarding members kept me for no reason to my Cary on bag

Sun, May 3
ORD
Chicago O'Hare Intl
SXM
Simpson Bay Princess Juliana
7h 36m
Thu, May 7
SXM
Simpson Bay Princess Juliana
ORD
Chicago O'Hare Intl
10h 50m
Trip: 5 days
7.4Good Show reviews
Overall 7.4 Good
Based on 43,737 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.9
Food
6.7
MIA
BCN
Good 6.0

Cons: My ticket did not allow me to use my status to upgrade. Never buying through Kayak again.

GCM
CLT
Good 6.4

Pros: Crew very friendly.

Cons: I could not get wifi. Had it from GCM to SAV with no problems.

DFW
SFO
Mediocre 3.5

Pros: I made it safely

Cons: Delayed twice, had to circle at destination, gate wasn’t ready.

CLT
AGS
Mediocre 3.3

Cons: Rebook travelers on a flight the same day if their original flight gets cancelled. Being held over for 48 hrs is. It acceptable.

EWR
CLT
Good 7.6

Pros: Yes the crow was good

Cons: The wifi should be free to use without paying for it

Sun, Apr 5
ORD
Chicago O'Hare Intl
SXM
Simpson Bay Princess Juliana
6h 58m
Tue, Apr 7
SXM
Simpson Bay Princess Juliana
ORD
Chicago O'Hare Intl
9h 17m
Trip: 3 days
8.1Excellent Show reviews
Overall 8.1 Excellent
Based on 27,965 reviews
Overall
8.1
Boarding
8.2
Comfort
7.8
Crew
8.5
Entertainment
7.8
Food
7.5
LAX
JFK
Good 7.0

Pros: Great crew.

Cons: Entertainment system malfunctioned constantly

MCO
LGA
Excellent 8.0

Pros: The flight attendants have so much patience, it’s amazing. Because passengers are idiots.

Cons: Do you really need to charge every person to pick their seat?

NRT
ATL
Excellent 10.0

Pros: Crew was amazing

Cons: Everything was pleasant

CMH
DTW
Good 7.0

Cons: Front right lav door hard to latch, headphones worked on one side only, gap in middle of lie-flat bed.

SJU
MSP
Excellent 10.0

Cons: Not a thing!

Fri, Jul 3
ORD
Chicago O'Hare Intl
SXM
Simpson Bay Princess Juliana
6h 35m
Sun, Jul 12
SXM
Simpson Bay Princess Juliana
ORD
Chicago O'Hare Intl
14h 58m
Trip: 10 days
Based on 0 reviews
Sat, Apr 25
ORD
Chicago O'Hare Intl
SXM
Simpson Bay Princess Juliana
7h 33m
Sat, May 2
SXM
Simpson Bay Princess Juliana
ORD
Chicago O'Hare Intl
10h 29m
Trip: 8 days
5.8Okay Show reviews
Overall 5.8 Okay
Based on 60,736 reviews
Overall
5.8
Boarding
6.2
Comfort
5.4
Crew
6.5
Entertainment
4.6
Food
4.8
FLL
LAX
Okay 4.0

Cons: No leg room. I am 6.3 and i got cuts on my knees from the front seat. I took pictures of the cuts but can't upload them here. Idk if i can sue the company, it's like discrimination if you are tall, you need to pay to fit. What about fat people that squeeze others?

MSY
LAX
Excellent 8.5

Pros: Ticket price, clean plane, comfortable seat, on time.

Cons: Crew needs to not behave like they work for a very cheap airline. Not a smile on their faces, not a single friendly sounding instruction or announcement from them. It doesn't cost them anything to act a bit more friendly.

EWR
CLT
Excellent 10.0

Pros: Convenience and easily accessible

Cons: Nothing

DTW
LAS
Mediocre 3.0

Cons: Computers that worked so we didn’t have 200 ppl waiting to check in. Reclining seats would be nice, trays that actually fit our computer. A flight that was on time. Entertainment. Will not fly Spirit again.

FLL
BWI
Mediocre 3.0

Cons: The seats are extremely uncomfortable

Sat, Apr 25
ORD
Chicago O'Hare Intl
SXM
Simpson Bay Princess Juliana
7h 33m
Tue, Apr 28
SXM
Simpson Bay Princess Juliana
ORD
Chicago O'Hare Intl
9h 17m
Trip: 4 days
5.8Okay Show reviews
Overall 5.8 Okay
Based on 60,736 reviews
Overall
5.8
Boarding
6.2
Comfort
5.4
Crew
6.5
Entertainment
4.6
Food
4.8
RSW
BOS
Mediocre 3.6

Pros: N Othing

Cons: The food or the drink a normal price. For a small bottle of water 3$ plus tax is no tax in the sky.

JAX
ORD
Mediocre 2.0

Pros: I like when the flight was over and I left the plane. This airline is the worst in the business.

Cons: The women at the gate rambled on and on each time she spoke. Rather than sticking to the boarding zones and keeping at that it was a constant annoying reminder about having to pay more money. The flight attendant don’t do their job. They spend more time Selling the credit card program than anything else. I was asked to put up another passengers seat tray as this passenger was asleep. This is not my job. They all stood in the front gossiping about who knows what instead of staying on the ready for the passengers. They look down upon and speak down upon. As If the crew was doing us a favor when it because of us they even have a job. Worst airline experience ever. I will never fly this airline again. The gate agents a check in couldn’t even speak proper English.

FLL
LAX
Okay 4.0

Cons: No leg room. I am 6.3 and i got cuts on my knees from the front seat. I took pictures of the cuts but can't upload them here. Idk if i can sue the company, it's like discrimination if you are tall, you need to pay to fit. What about fat people that squeeze others?

ATL
FLL
Mediocre 2.0

Pros: Nothing

Cons: Too much chaos at the gate, and late departure.

FLL
CMH
Excellent 10.0

Pros: The time

Tue, Aug 4
ORD
Chicago O'Hare Intl
SXM
Simpson Bay Princess Juliana
6h 57m
Tue, Aug 11
SXM
Simpson Bay Princess Juliana
ORD
Chicago O'Hare Intl
11h 29m
Trip: 8 days
8.2Excellent Show reviews
Overall 8.2 Excellent
Based on 18,973 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
7.9
Food
7.8
POS
FLL
Excellent 10.0

Pros: Vegetarian meal was delicious

Cons: Would be great if WiFi was available

JFK
LAS
Excellent 8.0

Cons: More rounds of drinks

RSW
HPN
Excellent 9.6

Pros: On the plane legroom was much appreciated. Very convenient airport as living in Fairfield County. Good departure time, although general flight delays (Feb 3rd - runway problems) meant long lines & very crowded airport, with limited eating facilities.

Cons: Return flight (Fort Myers to Westchester) flight was delayed - believe it was weather related & not the airlines fault.

HAV
JFK
Good 7.3

Cons: Tv wasn’t working

SFO
JFK
Excellent 9.6

Pros: Great crew. Great plane.

Cons: I feel like JetBlue used to have more/better movies

Sat, Apr 25
ORD
Chicago O'Hare Intl
SXM
Simpson Bay Princess Juliana
7h 33m
Tue, Apr 28
SXM
Simpson Bay Princess Juliana
ORD
Chicago O'Hare Intl
9h 17m
Trip: 4 days
5.8Okay Show reviews
Overall 5.8 Okay
Based on 60,736 reviews
Overall
5.8
Boarding
6.2
Comfort
5.4
Crew
6.5
Entertainment
4.6
Food
4.8
FLL
BWI
Mediocre 3.0

Cons: The seats are extremely uncomfortable

TPA
ATL
Excellent 10.0

Pros: Flight on time, smooth landing, nice and helpful crew.

SJO
FLL
Mediocre 2.0

Pros: Nothing

Cons: Everything

MSY
LAX
Excellent 8.5

Pros: Ticket price, clean plane, comfortable seat, on time.

Cons: Crew needs to not behave like they work for a very cheap airline. Not a smile on their faces, not a single friendly sounding instruction or announcement from them. It doesn't cost them anything to act a bit more friendly.

BUR
LAS
Okay 4.0

Pros: No

Cons: Be on time

Tue, Jun 9
ORD
Chicago O'Hare Intl
SXM
Simpson Bay Princess Juliana
7h 11m
Tue, Jun 16
SXM
Simpson Bay Princess Juliana
ORD
Chicago O'Hare Intl
11h 29m
Trip: 8 days
8.2Excellent Show reviews
Overall 8.2 Excellent
Based on 18,973 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
7.9
Food
7.8
BOS
JAX
Excellent 10.0

Pros: Bigger coach than other US airlines

Cons: Bigger lavatory in the plains

JFK
LAS
Excellent 8.0

Cons: More rounds of drinks

JFK
LAX
Excellent 9.0

Pros: Just overall solid experience, especially considering how terrible other airlines have become

PDX
JFK
Okay 5.5

Cons: Too long to get “maintenance sign off”

POS
FLL
Excellent 10.0

Pros: Vegetarian meal was delicious

Cons: Would be great if WiFi was available

Sun, May 3
ORD
Chicago O'Hare Intl
SXM
Simpson Bay Princess Juliana
7h 36m
Thu, May 7
SXM
Simpson Bay Princess Juliana
ORD
Chicago O'Hare Intl
10h 50m
Trip: 5 days
7.4Good Show reviews
Overall 7.4 Good
Based on 43,737 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.9
Food
6.7
ORD
FLL
Okay 4.6

Pros: super uncortable. everytime AA is shrinking their seats. wifi wasnt working and u have to pay

TPA
ORD
Mediocre 2.0

Cons: every single flight got changed multiple times worst experience

JFK
LHR
Mediocre 3.6

Pros: The price of the ticket was great.

Cons: The flight was crowded, no overhead bin space from passengers putting coats and jackets in the bin instead of under their seats. I was in the middle seat between two large men breathing down on me while they slept. It was a nightmare. On a flight that long the seats shouldn’t be that close in proximity nor should larger passengers be allowed to sit in seats too small for their body type. That’s not discrimination that’s logical.

GCM
CLT
Good 6.4

Pros: Crew very friendly.

Cons: I could not get wifi. Had it from GCM to SAV with no problems.

DFW
LAX
Good 6.6

Pros: Entertainment and air hostess

Cons: American Airlines have to improve with their food. Spend more than 500 for ticket and they cannot provide lunch for > 5 hour flight? We had to buy that food as well. They also boarded us too soon and didn't have time to grab the food outside as our time between flight is only 50 mins.

Sat, Mar 7
ORD
Chicago O'Hare Intl
SXM
Simpson Bay Princess Juliana
8h 09m
Sat, Mar 14
SXM
Simpson Bay Princess Juliana
ORD
Chicago O'Hare Intl
9h 57m
Trip: 7 days
5.8Okay Show reviews
Overall 5.8 Okay
Based on 60,736 reviews
Overall
5.8
Boarding
6.2
Comfort
5.4
Crew
6.5
Entertainment
4.6
Food
4.8
EWR
CLT
Excellent 10.0

Pros: Convenience and easily accessible

Cons: Nothing

LAS
OAK
Excellent 10.0

Pros: Price is good

Cons: If they can load passenger faster

MSP
PHX
Mediocre 3.5

Pros: We got to our destination

Cons: Deal with broken toilet BEFORE you board us. Attendants that can actually smile would be pleasant. Replace the park benches for actual airline seats.

BWI
CUN
Okay 5.6

Pros: Crew did just the minimum. We're not bad or good.

Cons: They want to charge even for water.

FLL
BWI
Mediocre 3.0

Cons: The seats are extremely uncomfortable

Tue, Jun 9
ORD
Chicago O'Hare Intl
SXM
Simpson Bay Princess Juliana
7h 11m
Tue, Jun 16
SXM
Simpson Bay Princess Juliana
ORD
Chicago O'Hare Intl
11h 29m
Trip: 8 days
8.2Excellent Show reviews
Overall 8.2 Excellent
Based on 18,973 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
7.9
Food
7.8
BOS
MCO
Excellent 10.0

Pros: Crew was nice. Seats very uncomfortable. Seems like they get smaller and smaller each time.

Cons: It was a 3+ hour flight. They should've given us something more than chips or cookies

SFO
FLL
Excellent 10.0

Cons: Excellent, one time, WiFi, Entertaiment screen, all good

RSW
HPN
Excellent 9.6

Pros: On the plane legroom was much appreciated. Very convenient airport as living in Fairfield County. Good departure time, although general flight delays (Feb 3rd - runway problems) meant long lines & very crowded airport, with limited eating facilities.

Cons: Return flight (Fort Myers to Westchester) flight was delayed - believe it was weather related & not the airlines fault.

LAS
JFK
Excellent 9.0

Cons: Movies didnt work

ATL
BOS
Excellent 10.0

Pros: Very easy and great reminder app

Cons: No

Sat, Mar 7
ORD
Chicago O'Hare Intl
SXM
Simpson Bay Princess Juliana
8h 09m
Sat, Mar 14
SXM
Simpson Bay Princess Juliana
ORD
Chicago O'Hare Intl
9h 57m
Trip: 7 days
5.8Okay Show reviews
Overall 5.8 Okay
Based on 60,736 reviews
Overall
5.8
Boarding
6.2
Comfort
5.4
Crew
6.5
Entertainment
4.6
Food
4.8
TPA
LGA
Good 7.5

Pros: Cheap, no frills.

Cons: Seating family members together, instead of forcing them to pay a "buy your own seat" fee.

ATL
FLL
Mediocre 2.0

Pros: Nothing

Cons: Too much chaos at the gate, and late departure.

MSY
LAX
Excellent 8.5

Pros: Ticket price, clean plane, comfortable seat, on time.

Cons: Crew needs to not behave like they work for a very cheap airline. Not a smile on their faces, not a single friendly sounding instruction or announcement from them. It doesn't cost them anything to act a bit more friendly.

LAS
EWR
Okay 4.0

Pros: The flight was fast and on time.

Cons: The seats are aweful. The two crew members stood in the back of the overnight flight, chatting loudly the whole time. Impossible to catch some sleep.

PIT
TPA
Excellent 8.0

Pros: Crew was friendly with humor

Cons: Seats We’re comfortable but as with most planes cramped

Wed, Jul 15
ORD
Chicago O'Hare Intl
SXM
Simpson Bay Princess Juliana
6h 35m
Thu, Jul 23
SXM
Simpson Bay Princess Juliana
ORD
Chicago O'Hare Intl
11h 29m
Trip: 9 days
7.4Good Show reviews
Overall 7.4 Good
Based on 43,737 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.9
Food
6.7
HPN
DCA
Excellent 10.0

Pros: service

Cons: offer coffee at least

PHL
DFW
Excellent 10.0

Pros: The salad was good.

JFK
LHR
Mediocre 3.6

Pros: The price of the ticket was great.

Cons: The flight was crowded, no overhead bin space from passengers putting coats and jackets in the bin instead of under their seats. I was in the middle seat between two large men breathing down on me while they slept. It was a nightmare. On a flight that long the seats shouldn’t be that close in proximity nor should larger passengers be allowed to sit in seats too small for their body type. That’s not discrimination that’s logical.

LAX
PHL
Excellent 8.0

Pros: Crew is friendly and seat is comfortable.

DAY
ORD
Good 7.5

Pros: Crew was good n seat could have been bigger.

Cons: Landing late to Chicago almost cost me my connection so I was stressed and could not eat due to limited time in between. The airline didn't notify us of being late to Chicago until I was on plane. We were told it was on time. Very disappointing..

Tue, May 19
ORD
Chicago O'Hare Intl
SXM
Simpson Bay Princess Juliana
7h 11m
Sat, May 30
SXM
Simpson Bay Princess Juliana
ORD
Chicago O'Hare Intl
10h 22m
Trip: 12 days
8.2Excellent Show reviews
Overall 8.2 Excellent
Based on 18,973 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
7.9
Food
7.8
PAP
JFK
Excellent 8.4

Pros: Flight was on-time, the crew was nice

Cons: Bluetooth enabled media

FLL
SFO
Excellent 9.0

Cons: First time flying with JET BLUE Loved It

ATL
BOS
Excellent 10.0

Pros: Very easy and great reminder app

Cons: No

BOS
FLL
Good 7.0

Cons: The video screen at my seat did not work. Otherwise the flight was great

LGA
FLL
Mediocre 2.0

Cons: JetBlue is awful. TVs don’t work. Staff isn’t friendly

Sun, Apr 5
ORD
Chicago O'Hare Intl
SXM
Simpson Bay Princess Juliana
6h 58m
Tue, Apr 7
SXM
Simpson Bay Princess Juliana
ORD
Chicago O'Hare Intl
9h 17m
Trip: 3 days
8.1Excellent Show reviews
Overall 8.1 Excellent
Based on 27,965 reviews
Overall
8.1
Boarding
8.2
Comfort
7.8
Crew
8.5
Entertainment
7.8
Food
7.5
LAX
JFK
Good 7.0

Pros: Great crew.

Cons: Entertainment system malfunctioned constantly

CMH
DTW
Good 7.0

Cons: Front right lav door hard to latch, headphones worked on one side only, gap in middle of lie-flat bed.

SLC
DEN
Excellent 9.2

Pros: The staff at Delta are always friendly and helpful and they were able to squeeze me onto a very full flight.

MSY
LAX
Good 6.6

Pros: Ok

Cons: So uncomfortable with tiny seats

BCN
JFK
Okay 4.0

Cons: Had no entertainment, asked the attendent, she called simebody, but it didn't help and she didn't bother to come and explain. Food was really bad, undercooked and cold.

Wed, Jul 15
ORD
Chicago O'Hare Intl
SXM
Simpson Bay Princess Juliana
6h 35m
Thu, Jul 23
SXM
Simpson Bay Princess Juliana
ORD
Chicago O'Hare Intl
11h 29m
Trip: 9 days
7.4Good Show reviews
Overall 7.4 Good
Based on 43,737 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.9
Food
6.7
EWR
CLT
Good 7.6

Pros: Yes the crow was good

Cons: The wifi should be free to use without paying for it

AUS
DFW
Mediocre 2.0

Pros: Nothing

Cons: The crew was rude, we took off over an hour late, there was no food for sale on board

OMA
CLT
Excellent 8.8

Pros: Crew

Cons: Seats small

GIG
JFK
Excellent 8.6

Cons: Better bathroom access for premium economy

PDX
LAX
Excellent 9.6

Pros: Very accommodating crew as we were traveling with my elderly grandmother.

Cons: Nothing really

Tue, May 19
ORD
Chicago O'Hare Intl
SXM
Simpson Bay Princess Juliana
7h 11m
Sat, May 30
SXM
Simpson Bay Princess Juliana
ORD
Chicago O'Hare Intl
10h 22m
Trip: 12 days
8.2Excellent Show reviews
Overall 8.2 Excellent
Based on 18,973 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
7.9
Food
7.8
DEN
BOS
Good 6.6

Cons: The tray table was very dirty when I put it down. I brought my own wipes but that was pretty bad.

BOS
FLL
Good 7.0

Cons: The video screen at my seat did not work. Otherwise the flight was great

MSY
FLL
Okay 4.5

Pros: Jet Blue's legroom

Cons: Too many delays

JFK
SYR
Excellent 9.0

Cons: Wifi didnt work. We were told at start of boarding

JFK
PSE
Excellent 8.0

Pros: It is the first time that a flight is delayed so much in the times that I have traveled in these last two years. But to catch the rest everything else was excellent. Jorge

Sat, May 9
ORD
Chicago O'Hare Intl
SXM
Simpson Bay Princess Juliana
7h 33m
Sat, May 16
SXM
Simpson Bay Princess Juliana
ORD
Chicago O'Hare Intl
10h 29m
Trip: 8 days
5.8Okay Show reviews
Overall 5.8 Okay
Based on 60,736 reviews
Overall
5.8
Boarding
6.2
Comfort
5.4
Crew
6.5
Entertainment
4.6
Food
4.8
EWR
CLT
Excellent 10.0

Pros: Convenience and easily accessible

Cons: Nothing

SJU
BOS
Mediocre 2.0

Pros: The crew need to be more professional and care the passenger.

Cons: The Spirit’s airline needs to be more reliable. Fourth hours delayed wasn’t funny.

PHX
SEA
Excellent 10.0

Cons: Everything

DEN
IAH
Mediocre 3.3

Cons: Mechanical problems caused 3+ hour delay. Missed being able to pick up my rental and didn't make for quite the same evening.

LAS
EWR
Okay 4.0

Pros: The flight was fast and on time.

Cons: The seats are aweful. The two crew members stood in the back of the overnight flight, chatting loudly the whole time. Impossible to catch some sleep.

*
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