$134 Find Cheap Flights from Chicago to St. Maarten

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 1/6. 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.
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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 Bay2 stops$355

Good to know

Low season

October

High season

March

Cheapest flight

$134
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 12% increase in price.
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 28% 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 4 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 8755 reviews
7.3Food
7.9Entertainment
8.2Boarding
7.9Comfort
8.5Crew
Airline reviews

I sat in comfort plus. It was fine. Seats were comfortable. I got drinks and snacks.

8.0 ExcellentAndrew, Nov 2024MCO - LGA
Read more Delta reviews

I sat in comfort plus. It was fine. Seats were comfortable. I got drinks and snacks.

Crew was nice. Flight was timely. Seats could be better as well as the food considering it’s first class.

Left on time and arrived early this extending our 31 minute transfer. Bags made it also!

Good and consistent Printer in lounge did not work for me :(

Most of my discomfort was going through TSA. However, the Delta seats had inadequate leg room and I tried my very best to connect to the wi-fi and it was a cumbersome process that finally gave me the info that I needed to sign in AFTER I had completed the flight...Why make it so difficult to use? That said I really really appreciate the pilot taking a little extra time to avoid a bad storm area and both landings in Atlanta and Orlando were flawless to my delight!!!

Delayed in taking off because no flight crew. The in seat entertainment was working properly.

All fine save for the abominable catering. Really gone downhill. We found it all inedible.

I upgraded to first class only to find out that I still had no access to the sky lounge without a sky miles card or AmEx (something that should be emphasized outside of the fine print!) Also, no food or drink service provided during the flight, so I basically paid 4x more just for “free” checked baggage and a bigger seat. Not worth it.

I appreciated friendly service from check-in, to boarding, to in-flight amenities! Attendants were accommodating and helpful. Thank you! Elaine

Delta was really good about being transparent with why we were delayed it’s just that’s the plane was really old and outdated and a lot of the comfort and amenities we know Delta to have did not shine through

They need to improve their boarding process. Group 1 and/or paying first class passengers shouldn't be in the middle of boarding process

late departure due to some unspecified issue with ventilating the cabin. They got it running but it was FREEZING for the whole flight. I asked for a blanket but they didn't provide one. They could not turn up the heat. it was quite miserable.

We were delayed because of ground crew, not because the plane wasn’t ready to go. The food was better than usual!

I still prefer Delta, but Delta doesn’t fly to State College PA.

Everything was fantastic. Modern plane. All the amenities! Although the paid snacks and meals are pure robbery. Like i understand airlines need to make money, but 11$ USD for an overnight oats with some nuts in it and barely any pieces of apple.... Highway robbery

United needs to figure out its Economy PLUS standards; its better than economy but that's not saying much. It seems like United stripped away all the basics for an international flight (such as In Seat entertainment) and repackaged some of them as plus. Would not fly United internationally again.

The flight was bumpy. No Breakfast or coffee was served, not even a bottle of water. The food was okay but odd. Rice with peas instead of couscous with some unknown green thing. United Airlines did not tell me that there was VERY LIMITED HANDICAP SERVICE IN NAPLES. De-plane via 20 aluminum steps. Taken to Van. You must walk into the terminal, find luggage, and then walk out to the rental car pickup spot that is 1 block from the terminal.

Crew did their best but the plane configuration is too tight if you're bigger than an average sardine. Controls for the entertainment system didn't all work. The aircraft hadn't been cleaned in awhile.

Flight was delayed due to weather and clogged toilet. Had to deplane. Flight was 3 hours delayed. Crew was awesome and offered water and snacks.

Didn't make it dir to delays - no support from United staff

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

I had a TERRIBLE experience with the AA crew. I believe it was disability-related. It’s unlikely I will fly AA again.

Baby cried a lot. Nothing anyone could do about it. Just part of flying.

The flight crew was fantastic! Which the seats had a small TV.

The flight was delayed till next day ! They kept delaying every 30 minutes then after 3 hours they delayed it till next day. We kept waiting in line standing more than an hour to get the hotel and meal vouchers. There was no communication at all. Everything was bad

Smoothe flight. Pilot and crew did a great job. Uncomfortable seat in this jet, felt worn out

seats were way too small. Too short of a flight to offer amenities.

The main problem was delay. The plane was at the gate early and bags were loaded. However, there was no crew for the flight. They were inbound from LGA and had to land and make their way to our gate. It took more than 40 minutes. Then, once the crew arrived and boarded, one of the crew members had to deplane and then a replacement crew member had to be found. It took another 40 minutes or so to get the final crew member. In all, we took off about 2 hours later than our scheduled departure time. Once in the air, the flight was great. Smooth most of the way. The crew was professional and efficient.

Perfect flight. Efficient boarding, on time take off and early arrival. Generally smooth flight.

American is a steady for me. I always get what I expect from them. Sincere effort to get me from one place to another.

Boarding was slow the scanner broke mid through boarding and they had to manually do it

Average, boarding was ok, the eye scanner broken mid way through boarding they ahd to do it manually. Did not eat any food, Not even water was offered for free.

Boarding attendant was rude. Crew on the plan were more interested in talking amongst themselves and did not ask parentage if they needed anything or even walk down the isles.

Flight was ok with exception of the multiple delays. As with all Spirit flights, the sights are extremely uncomfortable and lack leg space. However, the price savings is the plus.

WiFi didn’t work despite paying for it. Crew was nice.

I upgraded my ticket at the ticket counter and was not informed of the huge bottleneck at TSA pre check. It took me over an hour to get through the line at this small airport and although I ran to the gate and reached it prior to scheduled departure, it had already pushed pack. I missed the flight. Spirit rebooked me on a flight to Orlando that evening, which would require me to then rent a car and drive to FLL. For scheduling reasons, I determined it be would better to rent a car in Pensacola and drive it to my destination in FLL. Spirit called me that evening and asked me if I was going to board the plane. I explained no, for scheduling reasons. The person apologized and said I would receive a refund, but I have not heard back. Certainly, I ought to be refunded the upgrade I paid for at the counter.

The staff from LAX to New Orleans were rude but the staff from New Orleans to LAX were nice!

Did what they needed to do. Brought us from point A to point B timely and without issue. Boarding through deplaning smooth.

Direct 2.5 hour flight good. Free snacks and coffee, water, or soft drinks not available...bad.

Atlanta airport gate area floor and nearly all seats disgusting. Spirit airlines crew fantastic!!

Book cheap flights from Chicago to St. Maarten

Recent round-trip flight deals

1/13Mon
2 stops
15h 37mORD-SXM
1/18Sat
1 stop
8h 22mSXM-ORD
$355
12/13Fri
2 stops
19h 34mORD-SXM
12/20Fri
1 stop
27h 44mSXM-ORD
$367
1/17Fri
2 stops
17h 17mORD-SXM
1/25Sat
1 stop
8h 22mSXM-ORD
$368
1/4Sat
1 stopSpirit Airlines
7h 30mORD-SXM
1/10Fri
1 stopSpirit Airlines
9h 37mSXM-ORD
$402
1/4Sat
1 stopSpirit Airlines
7h 30mORD-SXM
1/10Fri
1 stopSpirit Airlines
9h 37mSXM-ORD
$404
1/22Wed
1 stopDelta
7h 16mMDW-SXM
1/29Wed
1 stopDelta
10h 40mSXM-MDW
$630
12/31Tue
2 stopsAmerican Airlines
9h 07mORD-SXM
1/21Tue
2 stopsAmerican Airlines
17h 11mSXM-ORD
$634
1/5Sun
2 stopsAmerican Airlines
9h 07mORD-SXM
1/12Sun
2 stopsAmerican Airlines
17h 06mSXM-ORD
$645
1/4Sat
1 stopDelta
8h 20mMDW-SXM
1/10Fri
1 stopDelta
10h 40mSXM-MDW
$655
2/8Sat
nonstopUnited Airlines
5h 07mORD-SXM
2/15Sat
nonstopUnited Airlines
5h 54mSXM-ORD
$665

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Recent one-way flight deals

1/6Mon
1 stop
20h 20mORD-SXM
$134
1/8Wed
1 stop
20h 20mORD-SXM
$136
1/6Mon
2 stops
16h 39mORD-SXM
$154
12/4Wed
1 stopSpirit Airlines
7h 30mORD-SXM
$183
1/7Tue
1 stopSpirit Airlines
19h 19mORD-SXM
$185
3/12Wed
2 stopsAmerican Airlines
8h 40mORD-SXM
$312
1/7Tue
1 stopDelta
7h 16mMDW-SXM
$312
1/4Sat
1 stopDelta
7h 11mMDW-SXM
$334
1/4Sat
nonstopUnited Airlines
5h 07mORD-SXM
$378
12/7Sat
nonstopUnited Airlines
5h 07mORD-SXM
$468

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Last minute flights from Chicago to St. Maarten

Last minute flight, train and bus deals

11/22Fri
multi-stop
21h 09mORD-SXM
11/25Mon
multi-stop
19h 55mSXM-ORD
$839
11/22Fri
multi-stop
21h 09mORD-SXM
11/26Tue
multi-stop
23h 09mSXM-ORD
$878
11/25Mon
multi-stopSpirit Airlines
7h 30mORD-SXM
11/30Sat
multi-stopSpirit Airlines
19h 55mSXM-ORD
$891
11/23Sat
multi-stopAmerican Airlines
15h 54mORD-SXM
11/26Tue
multi-stopAmerican Airlines
9h 30mSXM-ORD
$1,045
11/23Sat
multi-stopAmerican Airlines
15h 51mORD-SXM
11/26Tue
multi-stopAmerican Airlines
10h 35mSXM-ORD
$1,049
11/23Sat
multi-stopSpirit Airlines
7h 30mORD-SXM
11/30Sat
multi-stopSpirit Airlines
19h 55mSXM-ORD
$1,146
11/23Sat
nonstopUnited Airlines
5h 07mORD-SXM
11/26Tue
multi-stopUnited Airlines
16h 39mSXM-ORD
$1,200
11/22Fri
multi-stopDelta
6h 35mMDW-SXM
11/26Tue
multi-stopDelta
7h 46mSXM-MDW
$1,248
11/23Sat
nonstopUnited Airlines
5h 07mORD-SXM
11/30Sat
nonstopUnited Airlines
5h 54mSXM-ORD
$1,270
11/22Fri
multi-stopDelta
6h 35mMDW-SXM
11/25Mon
multi-stopDelta
7h 46mSXM-MDW
$1,273

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Everything you need to know for your flight from Chicago to St. Maarten

Cabin class types available on flights to St. Maarten

Cabin classes available on flights to St. Maarten. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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