$143+ Cheap flights from Chicago (CHI) to St. Maarten
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SXM
Nov 2 — Nov 91
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to St. Maarten with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Chicago to St. MaartenExplore the most affordable flight options available from Chicago to St. Maarten. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 3, 2026.
Explore the most affordable flight options available from Chicago to St. Maarten. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 3, 2026.
This Trip.com deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/21:55 pm -
1 stop22h 50m
Sun 12/64:45 pm -
1 stop22h 28m
Deal found 10/2![Air Canada logo]()
$359
This Air Canada deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/54:30 pm -
1 stop21h 15m
Fri 12/114:45 pm -
1 stop18h 23m
Deal found 9/29![Air Canada logo]()
$390
This Air Canada deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/54:30 pm -
1 stop21h 15m
Sat 12/123:45 pm -
2 stops19h 23m
Deal found 9/29![Air Canada logo]()
$394
This CheapOair deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2910:57 am -
2 stops26h 48m
Tue 12/83:45 pm -
1 stop25h 07m
Deal found 9/29![Air Canada logo]()
$396
This Trip.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/2510:15 am -
1 stop27h 30m
Sat 10/312:40 pm -
1 stop22h 27m
Deal found 9/29![Air Canada logo]()
$401
This Priceline deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/910:57 am -
2 stops25h 48m
Sun 12/134:45 pm -
2 stops17h 15m
Deal found 10/2![Air Canada logo]()
$405
This Southwest deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/298:40 pm -
2 stops17h 00m
Tue 12/83:20 pm -
2 stops16h 20m
Deal found 9/30![Southwest logo]()
$494
This Southwest deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/309:05 pm -
2 stops15h 15m
Fri 1/83:35 pm -
1 stop9h 15m
Deal found 9/30![Southwest logo]()
$536
This Southwest deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/115:10 am -
1 stop7h 55m
Fri 10/163:05 pm -
1 stop10h 20m
Deal found 9/30![Southwest logo]()
$538
This Delta deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/116:04 am -
1 stop6h 36m
Fri 10/163:05 pm -
1 stop8h 28m
Deal found 9/30![Delta logo]()
$557
This Southwest deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/308:55 pm -
2 stops15h 50m
Fri 11/64:40 pm -
2 stops18h 40m
Deal found 9/30![Southwest logo]()
$579
This Delta deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/186:04 am -
1 stop6h 36m
Fri 10/233:05 pm -
2 stops19h 27m
Deal found 10/2![Delta logo]()
$592
Best flights from Chicago to St. MaartenDiscover carefully curated flight deals from Chicago to St. Maarten that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 3, 2026.
Discover carefully curated flight deals from Chicago to St. Maarten that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 3, 2026.
This Copa Airlines deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/312:13 pm -
1 stop19h 12m
Sat 2/612:20 pm -
1 stop13h 51m
Deal found 10/1![Copa Airlines logo]()
$484
This Delta deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/316:00 am -
1 stop6h 40m
Fri 2/51:40 pm -
1 stop10h 30m
Deal found 9/30![Delta logo]()
$496
This Southwest deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/315:00 am -
1 stop7h 35m
Fri 2/53:35 pm -
1 stop9h 20m
Deal found 9/30![Southwest logo]()
$496
This United Airlines deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/308:40 am -
Nonstop5h 17m
Sat 2/62:10 pm -
Nonstop6h 01m
Deal found 10/1![United Airlines logo]()
$642
This Copa Airlines deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/307:35 am -
1 stop25h 46m
Sat 2/612:20 pm -
1 stop26h 26m
Deal found 9/28![Copa Airlines logo]()
$514
This Delta deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/16:00 am -
1 stop6h 45m
Thu 1/141:40 pm -
1 stop10h 30m
Deal found 9/29![Delta logo]()
$556
This Southwest deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/37:30 pm -
2 stops17h 05m
Wed 2/173:35 pm -
1 stop9h 15m
Deal found 9/29![Southwest logo]()
$579
This Delta deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/306:00 am -
1 stop8h 00m
Fri 2/51:40 pm -
1 stop10h 30m
Deal found 9/28![Delta logo]()
$556
This United Airlines deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/316:20 pm -
1 stop17h 30m
Sat 2/62:10 pm -
Nonstop6h 01m
Deal found 10/1![United Airlines logo]()
$661
This Copa Airlines deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/272:13 pm -
1 stop19h 12m
Sun 3/712:23 pm -
1 stop13h 21m
Deal found 9/28![Copa Airlines logo]()
$609
This Delta deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/267:00 pm -
1 stop15h 15m
Sat 1/304:05 pm -
1 stop19h 19m
Deal found 9/30![Delta logo]()
$556
This Southwest deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/315:15 pm -
2 stops19h 20m
Sat 2/62:30 pm -
1 stop8h 50m
Deal found 9/28![Southwest logo]()
$624
This Copa Airlines deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/202:13 pm -
1 stop19h 12m
Sun 2/2812:20 pm -
1 stop13h 48m
Deal found 9/28![Copa Airlines logo]()
$609
This Delta deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/15:20 pm -
2 stops16h 55m
Sat 2/65:25 pm -
1 stop17h 09m
Deal found 9/30![Delta logo]()
$561
This Delta deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/86:04 am -
1 stop6h 36m
Fri 11/134:05 pm -
1 stop8h 49m
Deal found 10/3![Delta logo]()
$587
This Delta deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/306:00 am -
1 stop8h 00m
Sat 2/65:25 pm -
1 stop18h 27m
Deal found 9/28![Delta logo]()
$616
This Delta deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/185:27 am -
1 stop7h 13m
Sat 10/243:05 pm -
1 stop9h 52m
Deal found 9/29![Delta logo]()
$621
This Delta deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/165:20 pm -
2 stops17h 10m
Tue 3/303:20 pm -
1 stop17h 19m
Deal found 10/1![Delta logo]()
$655
Last-minute flights from Chicago to St. MaartenDiscover last-minute flight deals from Chicago to St. Maarten. Data last updated October 3, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to St. Maarten. Data last updated October 3, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/115:10 am -
1 stop7h 55m
Fri 10/163:05 pm -
1 stop10h 20m
Deal found 9/30![Southwest logo]()
$538
This Delta deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/116:04 am -
1 stop6h 36m
Fri 10/163:05 pm -
1 stop8h 28m
Deal found 9/30![Delta logo]()
$557
This Delta deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/186:04 am -
1 stop6h 36m
Fri 10/233:05 pm -
2 stops19h 27m
Deal found 10/2![Delta logo]()
$592
This Air Canada deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/248:40 pm -
1 stop17h 05m
Sat 10/312:40 pm -
2 stops20h 43m
Deal found 9/28![Air Canada logo]()
$394
This Trip.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/2510:15 am -
1 stop27h 30m
Sat 10/312:40 pm -
1 stop22h 27m
Deal found 9/29![Air Canada logo]()
$401
This Southwest deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/308:55 pm -
2 stops15h 50m
Fri 11/64:40 pm -
2 stops18h 40m
Deal found 9/30![Southwest logo]()
$579
This Air Canada deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/89:21 pm -
1 stop16h 24m
Fri 11/134:45 pm -
1 stop18h 38m
Deal found 10/3![Air Canada logo]()
$406
This Travelocity deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/253:40 pm -
1 stop21h 05m
Tue 12/13:45 pm -
1 stop30h 07m
Deal found 9/29![Air Canada logo]()
$431
This Southwest deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/259:05 pm -
2 stops15h 10m
Tue 12/13:15 pm -
2 stops22h 50m
Deal found 9/29![Southwest logo]()
$603
This CheapOair deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2910:57 am -
2 stops26h 48m
Tue 12/83:45 pm -
1 stop25h 07m
Deal found 9/29![Air Canada logo]()
$396
This Southwest deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/298:40 pm -
2 stops17h 00m
Tue 12/83:20 pm -
2 stops16h 20m
Deal found 9/30![Southwest logo]()
$494
One-way flights from Chicago to St. MaartenSearch for one-way flight options from Chicago to St. Maarten. Find affordable one-way fares based on user searches. Data last updated October 3, 2026.
Search for one-way flight options from Chicago to St. Maarten. Find affordable one-way fares based on user searches. Data last updated October 3, 2026.
This Trip.com deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/21:55 pm -
1 stop22h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/3![Air Canada logo]()
$143
This CheapOair deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/285:58 pm -
2 stops43h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Air Canada logo]()
$159
This Air Canada deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2910:57 am -
2 stops26h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/3![Air Canada logo]()
$164
This Air Canada deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/315:54 pm -
2 stops20h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/3![Air Canada logo]()
$167
This Trip.com deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2910:15 am -
1 stop27h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Air Canada logo]()
$168
This Flightnetwork deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/38:45 am -
1 stop29h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![Air Canada logo]()
$170
This Orbitz deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/11:55 pm -
2 stops46h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Air Canada logo]()
$174
This Air Canada deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/301:55 pm -
2 stops22h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Air Canada logo]()
$179
This Justfly.com deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/12:00 pm -
2 stops22h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/3![Air Canada logo]()
$183
This Air Canada deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/308:50 pm -
1 stop15h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/3![Air Canada logo]()
$185
This Southwest deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/315:00 am -
1 stop7h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Southwest logo]()
$200
This Delta deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:04 am -
1 stop6h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Delta logo]()
$260
Find flight deals from Chicago to St. Maarten
Keep the following information in mind while searching for Chicago to St. Maarten flight deals. Data was last updated October 3, 2026.
Round-trip from | $359 (Trip.com) |
|---|---|
One-way from | $143 (Trip.com) |
Popular in | June |
Cheapest in | January |
Average price | $665 |
Good round-trip deal | $689 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to St. Maarten that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 3, 2026.
Use the filters below to find and compare flights from Chicago to St. Maarten that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSimpson Bay
MDW Chicago Midway - SXM Simpson Bay Princess Juliana
MDWSXM
Chicago Midway
Sun 1/31
8:30 pm-2:35 pm
2 stops16h 05m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$200
Quickest round-trip
ChicagoSimpson Bay
ORD Chicago O'Hare Intl - SXM Simpson Bay Princess Juliana
ORDSXM
Chicago O'Hare Intl
Wed 12/30
8:40 am-3:57 pm
Nonstop5h 17m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$245
ChicagoSimpson Bay
ORD Chicago O'Hare Intl - SXM Simpson Bay Princess Juliana
ORDSXM
Chicago O'Hare Intl
Sun 1/3
6:25 pm-12:15 pm
1 stop15h 50m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$249
ChicagoSimpson Bay
ORD Chicago O'Hare Intl - SXM Simpson Bay Princess Juliana
ORDSXM
Chicago O'Hare Intl
Tue 12/1
5:30 am-2:40 pm
1 stop7h 10m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$249
ChicagoSimpson Bay
ORD Chicago O'Hare Intl - SXM Simpson Bay Princess Juliana
ORDSXM
Chicago O'Hare Intl
Mon 12/28
8:40 am-3:57 pm
Nonstop5h 17m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$252
ChicagoSimpson Bay
ORD Chicago O'Hare Intl - SXM Simpson Bay Princess Juliana
ORDSXM
Chicago O'Hare Intl
Mon 11/2
9:06 pm-2:26 pm
2 stops15h 20m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$255
ChicagoSimpson Bay
MDW Chicago Midway - SXM Simpson Bay Princess Juliana
MDWSXM
Chicago Midway
Fri 10/30
6:04 am-1:40 pm
1 stop6h 36m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$260
ChicagoSimpson Bay
ORD Chicago O'Hare Intl - SXM Simpson Bay Princess Juliana
ORDSXM
Chicago O'Hare Intl
Thu 12/31
6:00 am-2:45 pm
1 stop6h 45m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$260
ChicagoSimpson Bay
ORD Chicago O'Hare Intl - SXM Simpson Bay Princess Juliana
ORDSXM
Chicago O'Hare Intl
Fri 10/30
5:27 am-1:40 pm
1 stop7h 13m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$260
ChicagoSimpson Bay
ORD Chicago O'Hare Intl - SXM Simpson Bay Princess Juliana
ORDSXM
Chicago O'Hare Intl
Wed 10/28
5:27 am-1:40 pm
1 stop7h 13m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$268
Showing 1-10 of 37 resultsSorted by cheapest first
Best time to book a flight from Chicago to St. Maarten
Have a flexible travel schedule? Discover the best time to fly to St. Maarten from Chicago with our price prediction graph.
ORD-SXM
MDW-SXM
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to St. Maarten
CHI-SX0
ORD-SXM
MDW-SXM
What is the cheapest month to book a flight from Chicago to St. Maarten?
Currently, February is the cheapest month in which you can book a flight from Chicago to St. Maarten (average of $573). Flying from Chicago to St. Maarten in June is currently the most expensive (average of $780). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
How often are flights from Chicago to St. Maarten delayed?
About 25% of weekly flights between Chicago and St. Maarten have experienced delays in the past year, with the average delay time being 105 minutes.
What is the most punctual flight time for Chicago to St. Maarten flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Saturday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to St. Maarten flights?
Over the last year, American Airlines have had the lowest number of delays on this route, with just 21% of flights being delayed.
How far ahead should I book a flight from Chicago to St. Maarten?
To ensure you get the cheapest price possible for a flight from Chicago to St. Maarten, you should look to book at least 51 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
Reviews of airlines servicing St. Maarten
Get insights into the airlines that provide service to St. Maarten. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to St. Maarten. Reviews last updated October 3, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andUnited Airlines from Chicago to St. Maarten by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.9
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Overall
7.9
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Overall
7.9
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Overall
7.9
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Overall
7.9
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Overall
7.9
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Related info for your journey
Find useful and relevant information for your journey from Chicago to St. Maarten. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to St. Maarten
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to St. Maarten by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to St. Maarten by cabin class
Find flights from Chicago to St. Maarten, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and St. Maarten flights
Browse other Chicago and St. Maarten flight options. Last updated on October 3, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 5 airlines flying from Chicago to St. Maarten
Discover the top 5 airlines that operate flights from Chicago to St. Maarten. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$240 | Average$392 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$389 | Average$711 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$410 | Average$750 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$482 | Average$607 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$501 | Average$744 | FlexibilityNo cancel fee | On-time71% |