$154 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 6/21. 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

KAYAK searches hundreds of travel sites at once for deals on flights to St. Maarten

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

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$382

Cheap Flight Deals from Chicago to St. Maarten (CHI-SX0)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to St. Maarten that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Chicago to St. Maarten

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Chicago to St. Maarten.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
Spirit Airlines Logo
5:05 am - 2:00 pmORD-SXM
7h 55m1 stop
Spirit Airlines Logo
3:05 pm - 8:50 amSXM-ORD
18h 45m1 stop
$382Spirit Airlines
Find Deal
Mon, Jun 2 - Mon, Jun 9
Spirit Airlines Logo
7:35 pm - 2:00 pmORD-SXM
17h 25m1 stop
Spirit Airlines Logo
3:05 pm - 8:50 amSXM-ORD
18h 45m1 stop
$387Spirit Airlines
Find Deal
Fri, May 9 - Mon, May 12
 Logo
5:05 am - 2:01 pmORD-SXM
7h 56m1 stop
 Logo
12:36 pm - 7:08 amSXM-ORD
19h 32m1 stop
Wed, Jul 16 - Sat, Jul 26
 Logo
5:05 am - 2:00 pmORD-SXM
7h 55m1 stop
 Logo
12:33 pm - 12:06 amSXM-ORD
12h 33m1 stop
Sat, May 31 - Sat, Jun 7
American Airlines Logo
5:00 am - 2:24 pmORD-SXM
8h 24m1 stop
American Airlines Logo
2:05 pm - 9:43 pmSXM-ORD
8h 38m1 stop
$622American Airlines
Find Deal
Sun, May 25 - Tue, Jun 3
American Airlines Logo
5:00 am - 2:24 pmORD-SXM
8h 24m1 stop
American Airlines Logo
2:24 pm - 12:11 amSXM-ORD
10h 47m2 stops
$627American Airlines
Find Deal
Sun, May 25 - Tue, Jun 3
Delta Logo
5:35 am - 2:00 pmORD-SXM
7h 25m1 stop
Delta Logo
3:25 pm - 11:59 pmSXM-ORD
9h 34m1 stop
$647Delta
Find Deal
Fri, Jun 20 - Thu, Jun 26
Delta Logo
6:00 am - 1:50 pmMDW-SXM
6h 50m1 stop
Delta Logo
3:15 pm - 9:44 pmSXM-MDW
7h 29m1 stop
$710Delta
Find Deal
Sat, Sep 13 - Sat, Sep 20
United Airlines Logo
6:00 am - 2:43 pmORD-SXM
7h 43m1 stop
United Airlines Logo
1:35 pm - 10:12 pmSXM-ORD
9h 37m1 stop
$1,162United Airlines
Find Deal
Sat, May 24 - Sat, May 31
United Airlines Logo
8:52 am - 11:20 amORD-SXM
25h 28m1 stop
United Airlines Logo
1:16 pm - 6:10 pmSXM-ORD
5h 54mnonstop
$2,716United Airlines
Find Deal
Sat, Oct 18 - Sat, Nov 1

KAYAK's insights & trends for Chicago to St. Maarten flights

Get data-powered insights and trends into flights from Chicago to St. Maarten to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago to St. Maarten flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago to St. Maarten.
The cheapest ticket to St. Maarten from Chicago found in the last 72 hours was to Simpson Bay, at $757 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Simpson Bay (SXM), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $757.

What is the cheapest time of day to fly to St. Maarten?

The average price for all round-trip flights from Chicago to St. Maarten depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.
The cheapest time of day to fly to St. Maarten is generally in the afternoon, when round-trip flights cost $417 on average. Morning departures are around 86% more expensive than evening flights, on average. The most expensive time of day to fly to St. Maarten is generally in the morning, which is peak travel time and where the average cost of a ticket is $913.

Can I save money by flying with a layover from Chicago to St. Maarten?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.
No, with an average price for the route of $1,354, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago to St. Maarten?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to St. Maarten, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Chicago to St. Maarten is September, when tickets cost $644 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $835 and $833 respectively.

What’s the cheapest day of the week to fly from Chicago to St. Maarten?

The average price of all round-trip flights from Chicago to St. Maarten clicked on KAYAK for each day over the last 12 months.
Your flight ticket price will generally be cheaper if you fly to St. Maarten on a Monday and more expensive on a Saturday. On your return trip to Chicago, you should consider flying back on a Monday, and avoid Sundays for better deals.

How far in advance should I book a flight from Chicago to St. Maarten?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to St. Maarten, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.
To get a below average price on the flight from Chicago to St. Maarten, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.

Good to know

Low season

August

High season

March

Cheapest flight

$154
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 13% 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 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 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 7920 reviews
7.9Comfort
8.2Boarding
7.9Entertainment
8.5Crew
7.3Food
Airline reviews

Delta flight was on time, seats were comfortable, and crew was nice.

8.0 ExcellentAnonymous, Apr 2025LAX - DEN
Read more Delta reviews

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

It was an overnight flight and I desperately needed coffee before we landed, but Delta does only one beverage service, and that is shortly after takeoff, not before landing at 5 am.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

After a 5 hour delay waiting at the gate (3 delays adding up) with no clear reason provided, we finally boarded flew 3/4 of the way to Toronto then were turned back to New York. As we neared New York, the pilot declared that it was his fault, something to do with timing and him not being allowed into the country???? How could the airline let his happen? They had hours to prepare and make sure they had a crew available for the flight! We ended up in Toronto a day late with no sleep.

The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

I do prefer to fly United and have always had excellent service, except for bad weather. Flights are on time and staff is alway curtious and helpful

They switched out gate from terminal 1 to terminal two ten minutes before boarding. So we had to make a 20 min crazy fast walk to a different terminal. Then we boarded the plane and waited for over 40 minutes until push back. Brutal

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

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.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

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..

terrible service, no room for a dog underfoot, a broken chair that is impossible to sit on and all this costs a lot of money

Easy boarding. Met expectations for a 2-3 hour flight. Early arrival at DFW caused a 39 minute delay on the tarmac in getting to our gate. 😏 overall, good flight.

Very efficient process and boarding, seats felt standard. Flight conditions from take off to landing had been very smooth. Alcohol on the menu however was not available… Will fly Spirit in the future for the price, you can’t really complain if you fly light.

It’s what we expected from Spirit..reasonable cost, good for a 2-3 hour flight. Disappointed that we had a 2 hour delay in departure from DFW for a maintenance issue, but the pilot handled it well once we were outbound on a different Airbus.

Worst airline ever! The guy weighing my bag had his foot on the metal plate and when I called him out on it, I got this stupid little smirk. La is a scam and so is Spirit Airlines. All the flight attendants looked like they hated our flight just as much as we did.

My experience with Spirit went pretty much as expected. It's a no frills airline, and you get what you pay for. I don't require much, so I was grateful to have an inexpensive way to travel. It is sad to me that the gate agents and flight crew don't smile much or seem very friendly or helpful. They are competent and efficient, and that's really all I need.

My experience was okay. The flight did not offer even water without a fee. Also had to pay extra for my carry on, as I was told I had to check my bag, even though it said I had the option to carry on a bag when booking. This costed me an extra $100. Would likely not fly with Spirit again.

The flight was rescheduled several times without a reason for the schedule changes. I had to be in New Orleans at a certain time and it was just easier to drive at a certain point. I don’t know if the flight ever left. This is my first experience with Spirit Airlines and is also the last.

It was fast but uncomfortable seats. Had to pay a bit extra not sure why? Maybe in selection of all my 4 tix together ? Just knew I had a balance before getting boarding pass online when departing from satx ? And flight was delayed..

In a word, it was horrible. The flight crew timed out and this, apparently was not accounted for by management. This meant that our 10:15 departure turned into a 1:30am departure the next DAY!!! And some brainchild decided to email us 12$ food vouchers set to expire the 9th, but they sent them after EVERY VENDOR WAS CLOSED in the Miami airport and obviously none would be open in New Orleans. I found this to be another sterling example of, at best, shitty management…at worst an absolute lack of empathy for your customers. Triplt Pro: Check-in may be avail for NK222 dep MIA 4/8/2025 10:16pm. Conf#RGSUMI. https://tripit.com/t/. e106fd644e0a; Today 6:16 PM TripIt Pro: NK222 ON TIME. MIA dep 10:16pm term C, gate F5. MSY arr 11:38pm. Today 8:59 PM Tript Pro: NK222 DELAYED. MIA dep 1:00am term C, gate F5. MSY arr 2:18am. Alternate flights: https:// www.tripit.com/t/b2903869f438 Triplt Pro: NK222 PULLED IN. MIA dep 12:30am term C, gate F5. MSY arr 1:48am. Alternate flights: https:/// www.tripit.com/t/834d176c630b Tript Pro: NK222 DELAYED. MIA dep 1:00am term C, gate F5. MSY arr 1:48am. Alternate flights: https:/// www.tripit.com/t/0441e41a9dd3 Triplt Pro: NK222 PULLED IN. MIA dep 12:30am term C, gate F5. MSY arr 1:48am. Alternate flights: https:// www.tripit.com/t/92ac2157ef54 The sender is not in your contact

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.

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.