$156 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 3/29. 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 from Chicago

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

Simpson Bay
Simpson Bay1 stop$316

Good to know

Low season

October

High season

March

Cheapest flight

$156
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 6% increase in price.
Flight from Chicago O'Hare Airport to Simpson Bay

FAQs - booking St. Maarten flights

  • How long is the flight to St. Maarten from Chicago?

    Flights to Simpson Bay0h 00m
  • What is the cheapest flight to St. Maarten from Chicago?

    The cheapest ticket to St. Maarten from Chicago found in the last 72 hours was $156 one-way, and $316 round-trip. The most popular route is from Chicago to Simpson Bay, and the cheapest round-trip airline ticket found on this route in the last 72 hours was $156.

  • Which airlines fly to St. Maarten?

    United Airlines flies most frequently to Simpson Bay from Chicago.

  • 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 from Chicago to St. Maarten 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 from Chicago to St. Maarten with an airline and back 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 from Chicago to St. Maarten 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

  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be January, November and December. The cheapest month to fly from Chicago is September.
  • Morning departure is around 67% 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 8068 reviews
8.2Boarding
7.9Entertainment
7.3Food
8.0Comfort
8.5Crew
Airline reviews

Delta is a premier airline so my expectations are most always met.

10.0 ExcellentGreg, Mar 2025PHX - MSP
Read more Delta reviews

Delta is a premier airline so my expectations are most always met.

Seats are much much more comfortable than United, which is what I usually fly

Zero updates from the pilots for 30 minutes in the tarmac

Boarding is, as it always is… horrible. Gate lice. Slow moving zones. Too many people with carry ons

I loved having a most black flight crew during Black History Month; rather by design or accident I appreciated the representation. ❤️

This was the second flight this week with flight attendant Marcus I’m not sure if his last name is Lane or Lang but this guy is awesome. He funny, attentive and his service is 5 stars. Marcus makes business travel more enjoyable !

Although the flight left late, we arrived early. It was one of the quickest boarding and off boarding experiences I’ve had. It was kind of annoying the only drinks they had were water, coffee, and tea. The flight was very smooth, temperature was just right, and flight attendants were friendly.

Rode in a smaller plane and short trip meant no snacks, no free wifi or tv. It was only 30min flight so honestly wasn’t a big deal to lack these items.

Lower number on this flight so spaced out passengers. Able to enjoy more room to relax during flight. It was lovely.

Kind staff. Snacks are small but that’s the new normal.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

The seats on this flight were almost roomy enough to be the basic amount needed for human existence.

Fight was delayed an hour due to operational issues ,then further delayed due to ground control for a total of about 1.30 hours. Salad was completely frozen and flatware was so cold you could barely handle it. Crew was friendly and professional and the flight was smooth. The aircraft was clean and well-serviced.

The flight attendants in First Class were mediocre at best. They did not take our tray away until we were about to land and only did so when I press the call button. The United person at the United Club was asked to get us our boarding pass since we missed the flight due in Chicago. She argued that we did not have seats on the flight given to us in Moline. Furthermore, she was adamant that we did not have a First Class ticket. After I spent much time with her trying to show we were correct, she reluctantly agreed. She was probably the most incompetent ticketing person I have ever met and I have traveled 3 million miles on United plus many additional miles with other carriers. United has definitely deteriorated in more than on way.

Short flight - no food understandable. Flight was delayed for over an hour. Overall, it was good.

We arrived early and finally made it to our gate almost an hour after.

Was a pain having to leave the plane and reboard but glad the plane was fixed

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

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.

Surprising everything went well. Nice attendants and fast getting on and off the plane. Overall, was happy with the experience.

Friendly staff put me at ease with processes, since this was my first time. I would recommend flying on Spirit!

I lijed the friendliness of the crew and that we were on time.

There should be a “Ticketing/Check In” section. A Spirit employee helped us operate the self-serve check-in kiosk, and he was very helpful. However, the ticket agent was another story. She took our (2) checked bags, but when placing them on the conveyor, dropped one of them - it fell over on the conveyor and broke the retractable handle. Two pieces of the handle broke away and landed behind the counter. She knew what had happened, but chose to ignore and moved on to the next person in line.

Pl meed tp make proper accom for all pets and owners by placing them on a section to accommodate human animal allergies and give up a few seats YWS ACCOMMODATIONS SHOULD BE MADEBY THE AIRLINES and not pushed off to another paying customer that has to sit in fear or by being touched by someone elses animal.

hassled about bringing my laptop on in addition to my backpack...people boarding with real luggage were not stopped but I was which was ridiculous....zero comfort on board and everything is extra. Last time flying spirit not worth it

A passenger got into a verbal altercation with the flight attendant, who neither de-escalated nor acted professionally. Because of this, we had to go back to the gate for the person to be kicked off the flight. It delayed us 75 minutes.

Our experience was not a good one. Our flight got cancelled and was not given any accommodations due to the inconvenience. We lost time on our vacation due to this inconvenience

Helpful flight attendant. Awful legroom. Airline should be required by law to offer people a glass of water.

They are very particular about size of the bag. Mine is small bag and has wheels. Bag wheel edges are bit outside of the measurements bucket. They charged $99 as carryon bagage

Book cheap flights from Chicago to St. Maarten

Recent round-trip flight deals

4/5Sat
1 stopSpirit Airlines
7h 50mORD-SXM
4/9Wed
1 stopSpirit Airlines
10h 15mSXM-ORD
$316
4/16Wed
1 stopSpirit Airlines
7h 24mORD-SXM
4/23Wed
1 stopSpirit Airlines
10h 15mSXM-ORD
$317
3/31Mon
1 stop
7h 41mORD-SXM
4/7Mon
1 stop
25h 05mSXM-ORD
$359
3/31Mon
1 stop
7h 41mORD-SXM
4/7Mon
2 stops
17h 29mSXM-ORD
$369
6/19Thu
2 stopsFrontier
45h 43mMDW-SXM
6/23Mon
2 stopsFrontier
45h 46mSXM-MDW
$525
5/30Fri
1 stopFrontier
12h 46mMDW-SXM
6/14Sat
1 stopFrontier
8h 41mSXM-MDW
$527
4/5Sat
1 stopAmerican Airlines
16h 57mORD-SXM
4/8Tue
1 stopAmerican Airlines
18h 25mSXM-ORD
$622
4/9Wed
1 stopDelta
6h 59mMDW-SXM
4/15Tue
1 stopDelta
9h 36mSXM-MDW
$622
4/5Sat
2 stopsAmerican Airlines
15h 33mORD-SXM
4/10Thu
1 stopAmerican Airlines
18h 30mSXM-ORD
$627
4/17Thu
1 stopDelta
7h 01mMDW-SXM
4/24Thu
1 stopDelta
9h 36mSXM-MDW
$647

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Recent one-way flight deals

3/29Sat
2 stopsSpirit Airlines
41h 15mORD-SXM
$156
3/29Sat
1 stopSpirit Airlines
7h 18mORD-SXM
$257
3/8Sat
2 stops
15h 51mORD-SXM
$268
3/8Sat
1 stopSpirit Airlines
7h 18mORD-SXM
$289
3/29Sat
3 stops
38h 05mORD-SXM
$311
3/15Sat
1 stopSpirit Airlines
7h 18mORD-SXM
$316
3/29Sat
nonstopUnited Airlines
5h 07mORD-SXM
$418
3/8Sat
nonstopUnited Airlines
5h 07mORD-SXM
$463
3/15Sat
2 stopsAmerican Airlines
9h 15mORD-SXM
$468
3/15Sat
1 stopDelta
7h 01mMDW-SXM
$578

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Last minute flights from Chicago to St. Maarten

Last minute flight, train and bus deals

3/5Wed
multi-stopSpirit Airlines
7h 18mORD-SXM
3/12Wed
multi-stopSpirit Airlines
10h 23mSXM-ORD
$589
3/8Sat
multi-stopSpirit Airlines
7h 18mORD-SXM
3/22Sat
multi-stopSpirit Airlines
10h 26mSXM-ORD
$603
3/8Sat
multi-stop
20h 42mORD-SXM
3/22Sat
multi-stop
10h 26mSXM-ORD
$634
3/8Sat
multi-stop
46h 57mORD-SXM
3/22Sat
multi-stop
23h 22mSXM-ORD
$763
3/7Fri
multi-stopAmerican Airlines
9h 15mORD-SXM
3/11Tue
multi-stopAmerican Airlines
10h 00mSXM-ORD
$962
3/7Fri
multi-stopAmerican Airlines
7h 45mORD-SXM
3/11Tue
multi-stopAmerican Airlines
11h 02mSXM-ORD
$967
3/8Sat
nonstopUnited Airlines
5h 07mORD-SXM
3/22Sat
nonstopUnited Airlines
5h 54mSXM-ORD
$1,155
3/8Sat
multi-stopUnited Airlines
13h 13mORD-SXM
3/22Sat
nonstopUnited Airlines
5h 54mSXM-ORD
$1,159
3/8Sat
multi-stopAir Canada
22h 50mORD-SXM
3/22Sat
multi-stopAir Canada
16h 12mSXM-ORD
$1,824
3/8Sat
multi-stopAir Canada
16h 25mORD-SXM
3/22Sat
multi-stopAir Canada
19h 09mSXM-ORD
$2,064

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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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