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Find cheap flights from Chicago to St. Maarten from $172

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to St. Maarten departing on 6/30. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Thu 7/11
Thu 7/18

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Best St. Maarten Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Simpson Bay
Simpson Bay1 stop$240

Good to know

Low season

September

High season

February

Cheapest flight

$172
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly and prices are also 4% lower on average.
Flight from Chicago O'Hare Airport to Simpson Bay

FAQs - booking St. Maarten flights

  • How does KAYAK find such low prices on flights from Chicago to St. Maarten?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to St. Maarten.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to St. Maarten?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to St. Maarten from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to St. Maarten?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to St. Maarten with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to St. Maarten?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to St. Maarten from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to St. Maarten

  • Morning departure is around 58% 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

Top 5 airlines serving from Chicago to St. Maarten

Need help choosing which airline to fly with from Chicago to St. Maarten? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 10277 reviews
8.2Boarding
8.0Entertainment
7.4Food
7.9Comfort
8.6Crew
Airline reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

2.0 MediocreCraig, Jun 2024CVG - LGA
Read more about Delta reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

Among the poorest flights I’ve had with Delta in a while. Entertainment system failed completely on a 7.5 hr flight. Crew seemed distracted and not the normal friendly crew. Flight overbooked it seemed… very crowded.

If I can, I always fly Delta. I’ve found their service to always be reliable and pleasant.

You could have not cancelled the flight (AA, which I will be flying from now on) left for BOS despite the fictitious weather issues (that no one in my Boston family could see). You could have rebooked my direct flight to another direct flight instead of sending me though JFK, the worst US airport after O’Hara You could have rebooked me on a Main Cabin seat (like the one I paid for in my original ticket instead of putting me a the last row on JFK->BOS leg, pocketing the difference in ticket price But I do not really care whether you will ever do that in a future because in a future neither I nor anyone from my company (unless they pay out of pocket) nor an of my clients and partners (if they heed my advice) will ever be caught dead on any of Delta flights

Really bad baggage handling. Had my Rimowa bag badly damaged at the latches.

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

I've flown many many times on Northwest and then Delta. The crew on this flight were absolutely the best I've had the pleasure of being looked after by.

The seats had plenty of leg room and the staff were very nice.

Copa performed as expected for the amount of money I was willing to spend for the flight; it wasn’t exceptional but it was not bad in any way either. The crew was good; friendly and straightforward. The food was airplane food, so no expectations there and the entertainment was lacking but that was my fault for owning an IPhone with a charging port that’s not compatible with the rest of the world. I’d fly Copa again.

Left my bags in origin city on a business class ticket , spent about 2-3 days in the same clothes plus the flight .

the planes are not modern there are no phone chargers

As usual, the flight with normal legroom was not very comfortable, but the second flight was much better because we had paid for extra legroom. It was very nice to check our bags without an extra fee.

LOCKED MY BAG WITHOUT CONSENT. Had to have my zippers cut upon arrival in Costa Rica.

Pros: "The seats in economy were confortable. The best thing was Copa gave us seats in the second line and my family traveled together."
Cons: "Coffe service could better the experience"
Pros: "The crew was very interested on help and attentive with the passengers. But the seat wasn't comfortable. The design of the cushion is not the best to be seating"
Pros: "You were on time, that is the most important thing in a fly"
Cons: "You could improve your entertainment, you are not a cheap company"
Pros: "That there was seltzer"
Cons: "The management of preparing the flight and plane so that it was ready for the trip!!"

Flighty delayed on boarding - then group 1 had to check their carry on bags but groups 3 and beyond could carry bags on - very inconvenient for weekend business trip with no checked baggage. Then delayed on the runway - before take off. No communication from pilot on why or how long. Wifi/Entertainment didn't work for 4+ flight. Upon arrival, attendants announced wrong carousel for baggage claim - everyone was waiting at the wrong place for their checked bags. This was a mess united!

There was no screens on board AND the WiFi didn’t work. My seat was broken and couldn’t recline so I couldn’t even sleep. The flight attendants didn’t offer anything to make it more comfortable. It was such an old cramped plane, when the person in front of me reclined I couldn’t even open my tray table. All the United ads talk about guaranteeing everyone gets a screen!

Standard flight experience, but there is only power at the seat to row 20 on the aircraft, on my initial check in it did not say that was the case

Energetic crew - flight full of swiftied going to Taylor's opening show in Paris! Long lines for bathroom made out kind of suck though

I’ve had a couple flights this week on United that were delayed by an hour or more

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

Nothing beats ANA customer service on my opinion. Maybe because of their Japanese culture (and food). Arigatō

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

Flight delayed for 2 hours due to a part. The plane sat waiting for boarding for a long time and during final preflight inspection the issue was found. Why not do the preflight inspection sooner if you know the plane is being used?

My husband and I pre-ordered our food, but they did not have my husband’s order, and my cheese plate was very average. I asked for a blanket and was told they don’t carry blankets on domestic routs. The flight was on time and smooth!

Original flight delayed several times and finally canceled at 2:30 in the morning. Staff at the gate was not very helpful in resolving problems or communicating why there were delays. I spent 34 hours at the airport before I could leave, they couldn't book me on another early flight even after canceling my original flight. Next flight available after my original flight was canceled was 22 hours later. I will never fly American Airlines again.

It was spectacular. I had basic Economy and was given so much space and their seats lean back so far. Staff was superb, food was superb, everything was superb, Finnair is Fantastic.

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

We were delayed bc ground crew gave the flight crew the wrong paperwork. We taxiied to the runway then back to the gate to get the correct paperwork that no one bothered reviewing the first time we pushed back. Boarding was rude and stressful like it always is. Gate agents and flight attendants are all over 55 years of age, embittered by years of underpayment From AA leading to their passive agressive bitchiness for no reason.

Boarding time was easy & quick. Crew was excellent. In-flight entertainment was great/easy. Seats are too small and not enough room between rows: felt like a sardine/very cramped.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

My flight was uncomfortable and crammed. There were no pockets to store things, I couldn’t move my seat back slightly. Beverages including soda cost extra. My husband flew on another spirit airline flight, which was delayed a total of 48 hours, only to be canceled.

Two delays in less than 24hrs. They need to improve everything and restructure the whole company.

Terrible leg room, seats don’t recline, delayed flight, and even water isn’t free onboard

Flight was canceled less than 6 hours before takeoff, rebooked on a flight that was twice as long and left earlier so we couldn’t make it, when using text support option took over 2 hours to speak with someone.

Not enough help at airport during boarding process. Flight was delayed. Overall WORST flying experience I’ve ever had. Will NEVER FLT SPIRIT AGAIN

Terrible legroom, seats do not recline, tray table the size of an iPhone, delayed flight, have to pay 5$ to get a cup of water onboard.

Could have TV/Movie and some water ou soda free

Flight was good and clean but delayed over an hour on the return flight.

The non stop flight and able to go into Atlantic City airport. They could lower the prices. It starts out low but then if you want to bring luggage and pick your seat the price goes up quite a bit.

Flight got diwngraded last minute and left us stranded. I was told I’ll be given credit for my luggage and seat upgrades but haven’t got anything yet

Book cheap flights from Chicago to St. Maarten

Recent round-trip flight deals

9/6Fri
1 stopFrontier
20h 22mORD-SXM
9/14Sat
2 stopsFrontier
18h 04mSXM-ORD
$240
9/6Fri
2 stopsFrontier
19h 35mORD-SXM
9/14Sat
2 stopsFrontier
18h 04mSXM-ORD
$261
7/10Wed
1 stopSpirit Airlines
8h 05mORD-SXM
7/17Wed
1 stopSpirit Airlines
27h 41mSXM-ORD
$351
9/5Thu
1 stopSpirit Airlines
19h 33mORD-SXM
9/9Mon
1 stopSpirit Airlines
26h 39mSXM-ORD
$372
8/21Wed
2 stopsAmerican Airlines
8h 37mORD-SXM
8/30Fri
2 stopsAmerican Airlines
16h 05mSXM-ORD
$559
10/2Wed
1 stopDelta
6h 50mMDW-SXM
10/9Wed
2 stopsDelta
18h 26mSXM-MDW
$559
8/16Fri
1 stopDelta
6h 45mMDW-SXM
8/30Fri
1 stopDelta
7h 36mSXM-MDW
$580
7/27Sat
nonstopUnited Airlines
5h 06mORD-SXM
8/3Sat
nonstopUnited Airlines
5h 44mSXM-ORD
$680
7/27Sat
1 stopUnited Airlines
14h 07mORD-SXM
8/3Sat
nonstopUnited Airlines
5h 44mSXM-ORD
$685
8/1Thu
2 stopsAmerican Airlines
24h 45mORD-SXM
8/4Sun
1 stopAmerican Airlines
8h 36mSXM-ORD
$729

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Recent one-way flight deals

6/30Sun
1 stopSpirit Airlines
18h 08mORD-SXM
$172
6/22Sat
2 stops
45h 09mORD-SXM
$181
6/22Sat
1 stopSpirit Airlines
7h 43mORD-SXM
$187
6/30Sun
2 stopsSpirit Airlines
15h 11mORD-SXM
$212
7/6Sat
1 stopDelta
6h 55mMDW-SXM
$347
7/6Sat
nonstopUnited Airlines
5h 06mORD-SXM
$388
7/3Wed
3 stopsWestJet
26h 43mMDW-SXM
$430
6/30Sun
1 stopDelta
6h 55mMDW-SXM
$462
6/22Sat
2 stopsWestJet
29h 42mMDW-SXM
$1,563
6/22Sat
nonstopUnited Airlines
5h 06mORD-SXM
$2,933

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Last minute flights from Chicago to St. Maarten

Last minute flight, train and bus deals

6/14Fri
multi-stop
20h 12mORD-SXM
6/19Wed
multi-stop
9h 09mSXM-ORD
$499
6/15Sat
multi-stopSpirit Airlines
7h 43mORD-SXM
6/19Wed
multi-stopSpirit Airlines
9h 09mSXM-ORD
$540
6/13Thu
multi-stopSpirit Airlines
18h 08mORD-SXM
6/19Wed
multi-stopSpirit Airlines
9h 09mSXM-ORD
$570
6/15Sat
multi-stopSpirit Airlines
7h 43mORD-SXM
6/22Sat
multi-stopSpirit Airlines
9h 09mSXM-ORD
$584
6/15Sat
multi-stopSpirit Airlines
7h 43mORD-SXM
6/19Wed
multi-stopSpirit Airlines
22h 16mSXM-ORD
$602
6/15Sat
multi-stopSpirit Airlines
7h 43mORD-SXM
6/22Sat
multi-stopSpirit Airlines
18h 50mSXM-ORD
$614
6/13Thu
multi-stopSpirit Airlines
18h 08mORD-SXM
6/19Wed
multi-stopSpirit Airlines
22h 16mSXM-ORD
$630
6/15Sat
nonstopUnited Airlines
5h 06mORD-SXM
6/22Sat
nonstopUnited Airlines
5h 44mSXM-ORD
$1,043
6/15Sat
multi-stopUnited Airlines
7h 43mORD-SXM
6/22Sat
nonstopUnited Airlines
5h 44mSXM-ORD
$1,048
6/13Thu
multi-stopAmerican Airlines
8h 34mORD-SXM
6/19Wed
multi-stopAmerican Airlines
22h 55mSXM-ORD
$1,064

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Flights to St. Maarten

Return flight deals:

St. Maarten - Chicago

Cabin classes:

$1,261
$2,013
$680