$126 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 3/3. 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

Search 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 23% 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$331

Good to know

Low season

October

High season

March

Cheapest flight

$126
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 7% 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 $126 one-way, and $331 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 $126.

  • 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 June, July and August. The cheapest month to fly from Chicago is February.
  • Morning departure is around 16% 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 8456 reviews
8.5Crew
7.3Food
7.9Entertainment
8.2Boarding
8.0Comfort
Airline reviews

Great service. Great staff. Boarding was a little slow, but I think there was a service dog slowing things down.

10.0 ExcellentD, Jan 2025ABE - ATL
Read more Delta reviews

Great service. Great staff. Boarding was a little slow, but I think there was a service dog slowing things down.

Flight left early and arrived early. the whole trip was excellent.

Seats were really tight and the seat belts did not give enough slack.

I like in St George and prefer to fly out of CDC than SGU. Hopefully, they will continue the flights out of Cedar

Broken jer bridge. Poor communication about it. Lost 2 of 4 luggage pieces

Overall, it was okay. Seat was a little cramped. Would’ve liked more substantial snacks or opportunity to buy some.

Newer plane, relatively easy boarding, not a full flight and was told that we could not be moved up because of weight and balance issues. Otherwise, a very good experience.

Other then mechanical/ computer problem and 3.5 hours flight delay the flight was great. I guess that what happened when you fly an old airplane now a day.

I was with one of the last zones to board. It was kind of annoying to finally get called to board and my whole section was already on the plane. Clearly they boarded with previous zones. So by the time I got on board, there were no spaces for my luggage above my head. I had to put my luggage 4+ rows behind me, which meant that I had to wait even longer to get off the plane, since I had to wait for those rows to clear the aisle before I could retrieve my luggage and exit the plane. This also held up the plane cleaners, as they couldn't service my row until I cleared it, so they were all standing there waiting for me, while I'm standing there waiting for the other passengers to clear the aisle. Anyways, I wasn't in a rush this time, so I just waited, but I could see that being a problem in the future. Now, I could have checked my luggage, of course, but coincidentally, a friend of mine on the same flight got their luggage damaged (wheel completely knocked off) and was told by the Baggage Attendant in the airport that Delta doesn't "cover wheel damage" on luggage. This was disappointing to hear. I'm glad I didn't check mine through. If it were my luggage, I'd be highly frustrated to hear that. It makes me not want to check my luggage in the future.

The dear was very limited in space. I could put my water bottle in seat basket. Also, there was no inflight entertainment in the delta app?

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

Plane was was better than th YVR to ORD flight but was a fraction of the distance. Fly your better planes on longer distance flights.

Nothing wrong with the flight itself. But due to 2+ hrs waiting in immigration and the additional security checkup in O’hare, I nearly missed the flight.

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

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.

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

You get what you pay for with this airline. If you want comfort be ready to pay, the regular seats are like hard plastic bus seats and they don't recline, so again you get what you pay for, a cheap flight that is just alright. Which is what I wanted.

Stop nickel and diming passengers with different seat costs, paying for water, carry on luggage, etc.

Boarding was smooth and on time. Flight itself was smooth (aside from some turbulence) and no glitches. On the downside, Spirit's no-frills service was as expected (no food or drink, cramped seating, extra cost for carry-ons, etc.), the announcements were nearly incomprehensible, and the constant niggling offers of upgrades and other services for sale (wifi, sandwiches, etc.) is annoying. Overall, a pleasant and uneventful experience - definitely worth the price.

Lower cost is the reason to fly Spirit. Should give free baggage with credit card.

From gate to flight crew... All Spirit employees were great! Everyone was kind and helpful. Ride was almost smooth... A few bumps... But no problems. Seats were tight and uncomfortable. Our biggest issue was no free drinks. I can understand paying for adult beverages and can understand no snacks on a 3 hour flight... But no drinks???? I had to pay $4 for an apple juice for my son. That's not right. You should probably reconsider that.

Loved staff help @ kiosk, staff on airplane. Commitment to punctuality. I sat in a "blocked" row, where the middle seat had no passenger & loved it! I appreciate not having to pay for water, which I've experienced even on international flights. Only negative was how dirty the bathroom was for a 4.5 hrs flight. But I don't think flight attendants monitor this.

- flight attendants not very friendly. - Paid for WiFi and plane didn’t have it working , never got a refund.

Great! First time flying with Spirit and I definitely loved it!

Not efficient. Missed my connecting flight over improper operation of spirit crew.

Very difficult. Flew out on Dec 24th and it was a mess. They know it is going to be the busiest time of the year and they had no organization. Finally they called for people going on certiam flights so they could get them thru thw line then we had to rush to our gate to get in li e to board.We missed our flight do to being stuck at the border of Mexico. They would not work with us to make an affordable price so we had to wait a day with no where to go and pay 280 more for our flights. I would think that a complimentary drink would be nice. But we had to pay 4.49 for a coke. Not an overall good experience

Book cheap flights from Chicago to St. Maarten

Recent round-trip flight deals

3/5Wed
1 stopSpirit Airlines
7h 18mORD-SXM
3/12Wed
1 stopSpirit Airlines
10h 23mSXM-ORD
$331
2/28Fri
1 stopSpirit Airlines
7h 30mORD-SXM
3/7Fri
1 stopSpirit Airlines
10h 23mSXM-ORD
$336
2/28Fri
2 stops
17h 12mORD-SXM
3/7Fri
1 stop
18h 01mSXM-ORD
$357
3/5Wed
2 stops
26h 35mORD-SXM
3/12Wed
1 stop
10h 23mSXM-ORD
$402
5/21Wed
2 stopsFrontier
51h 40mORD-SXM
5/26Mon
2 stopsFrontier
48h 53mSXM-ORD
$524
5/30Fri
2 stopsFrontier
19h 14mMDW-SXM
6/14Sat
2 stopsFrontier
12h 37mSXM-MDW
$557
3/23Sun
1 stopAmerican Airlines
17h 12mORD-SXM
4/3Thu
1 stopAmerican Airlines
16h 07mSXM-ORD
$642
3/30Sun
1 stopDelta
7h 01mMDW-SXM
4/9Wed
1 stopDelta
9h 41mSXM-MDW
$642
3/23Sun
1 stopAmerican Airlines
17h 12mORD-SXM
4/3Thu
2 stopsAmerican Airlines
15h 09mSXM-ORD
$647
4/16Wed
1 stopDelta
6h 57mMDW-SXM
4/20Sun
1 stopDelta
9h 07mSXM-MDW
$667

Search by stops

Search by airline

Search by price

Recent one-way flight deals

3/3Mon
1 stopSpirit Airlines
7h 30mORD-SXM
$126
3/3Mon
2 stopsSpirit Airlines
42h 44mORD-SXM
$146
3/3Mon
3 stopsSpirit Airlines
41h 15mORD-SXM
$153
2/6Thu
2 stopsSpirit Airlines
29h 30mORD-SXM
$244
2/6Thu
3 stopsSpirit Airlines
30h 40mORD-SXM
$266
2/6Thu
1 stopAir Canada
24h 10mORD-SXM
$279
2/6Thu
3 stops
20h 22mMDW-SXM
$321
2/6Thu
2 stops
25h 25mMDW-SXM
$371
2/6Thu
1 stopDelta
7h 16mMDW-SXM
$478

Search by stops

Search by airline

Search by price

Last minute flights from Chicago to St. Maarten

Last minute flight, train and bus deals

2/1Sat
multi-stopAir Canada
26h 20mORD-SXM
2/5Wed
multi-stopAir Canada
28h 22mSXM-ORD
$572
2/4Tue
multi-stopAir Canada
22h 15mORD-SXM
2/9Sun
multi-stopAir Canada
22h 16mSXM-ORD
$578
2/1Sat
multi-stopAir Canada
30h 35mORD-SXM
2/9Sun
multi-stopAir Canada
29h 00mSXM-ORD
$596
2/3Mon
multi-stopSpirit Airlines
7h 19mORD-SXM
2/5Wed
multi-stopSpirit Airlines
10h 07mSXM-ORD
$678
2/3Mon
multi-stopSpirit Airlines
7h 19mORD-SXM
2/7Fri
multi-stopSpirit Airlines
21h 55mSXM-ORD
$703
2/2Sun
nonstopUnited Airlines
5h 07mORD-SXM
2/9Sun
nonstopUnited Airlines
5h 54mSXM-ORD
$968
2/2Sun
nonstopUnited Airlines
5h 07mORD-SXM
2/9Sun
multi-stopUnited Airlines
18h 49mSXM-ORD
$978
2/1Sat
multi-stopDelta
7h 31mORD-SXM
2/6Thu
multi-stopDelta
9h 06mSXM-ORD
$1,022
2/1Sat
multi-stopDelta
8h 35mORD-SXM
2/4Tue
multi-stopDelta
9h 06mSXM-ORD
$1,032
2/2Sun
multi-stopAmerican Airlines
9h 01mORD-SXM
2/6Thu
multi-stopAmerican Airlines
18h 41mSXM-ORD
$1,042

Search by stops

Search by airline

Search by price

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.