$212+ Cheap flights from St. Maarten to Chicago (CHI)
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 11/12. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — CHI
Nov 6 — Nov 131
Round-trip
1 adult, Economy
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Cheapest flights from St. Maarten to ChicagoExplore the most affordable flight options available from St. Maarten to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 7, 2026.
Explore the most affordable flight options available from St. Maarten to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 7, 2026.
This Trip.com deal was found by Cheapflights users on 10/4. 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.
Mon 11/304:45 pm -
1 stop24h 53m
Wed 12/23:45 pm -
1 stop21h 00m
Deal found 10/4![Air Canada logo]()
$345
This Trip.com deal was found by Cheapflights users on 10/4. 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.
Mon 11/304:45 pm -
1 stop24h 53m
Thu 12/312:50 pm -
1 stop24h 55m
Deal found 10/4![Air Canada logo]()
$349
This Air Canada deal was found by Cheapflights users on 10/4. 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.
Fri 12/44:45 pm -
1 stop18h 23m
Mon 12/73:45 pm -
1 stop21h 00m
Deal found 10/4![Air Canada logo]()
$394
This Air Canada deal was found by Cheapflights users on 10/4. 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 12/14:45 pm -
1 stop28h 20m
Sat 12/510:05 am -
1 stop27h 40m
Deal found 10/4![Air Canada logo]()
$408
This Booking.com deal was found by Cheapflights users on 10/4. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/14:45 pm -
2 stops17h 15m
Fri 12/48:45 am -
2 stops28h 00m
Deal found 10/4![Air Canada logo]()
$415
This Booking.com deal was found by Cheapflights users on 10/4. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/14:45 pm -
1 stop30h 03m
Thu 12/310:05 am -
2 stops50h 40m
Deal found 10/4![Air Canada logo]()
$427
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/13:45 pm -
1 stop21h 22m
Wed 12/23:45 pm -
1 stop21h 00m
Deal found 10/2![Air Canada logo]()
$438
This Delta deal was found by Cheapflights users on 10/4. 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.
Thu 11/264:05 pm -
1 stop8h 49m
Sun 11/296:00 am -
1 stop6h 37m
Deal found 10/4![Delta logo]()
$491
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.
Thu 12/34:05 pm -
1 stop8h 49m
Sun 12/66:41 pm -
2 stops17h 59m
Deal found 10/2![Delta logo]()
$506
This Southwest deal was found by Cheapflights users on 10/6. 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 11/204:40 pm -
1 stop8h 30m
Fri 11/277:00 am -
1 stop6h 40m
Deal found 10/6![Southwest logo]()
$543
This Southwest deal was found by Cheapflights users on 10/4. 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 11/183:15 pm -
2 stops16h 25m
Wed 11/259:05 pm -
2 stops15h 10m
Deal found 10/4![Southwest logo]()
$570
This Delta deal was found by Cheapflights users on 10/4. 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.
Thu 11/264:05 pm -
1 stop8h 49m
Sat 12/56:00 am -
1 stop6h 45m
Deal found 10/4![Delta logo]()
$577
Best flights from St. Maarten to ChicagoDiscover carefully curated flight deals from St. Maarten to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 7, 2026.
Discover carefully curated flight deals from St. Maarten to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 7, 2026.
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.
Fri 12/44:45 pm -
1 stop18h 23m
Mon 12/73:45 pm -
1 stop21h 00m
Deal found 10/3![Air Canada logo]()
$394
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/252:10 pm -
Nonstop6h 01m
Sat 1/28:40 am -
Nonstop5h 17m
Deal found 10/2![United Airlines logo]()
$487
This Delta deal was found by Cheapflights users on 10/4. 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.
Thu 11/264:05 pm -
1 stop8h 49m
Sun 11/296:00 am -
1 stop6h 37m
Deal found 10/4![Delta logo]()
$491
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/294:39 pm -
2 stops15h 46m
Mon 11/27:50 pm -
1 stop16h 36m
Deal found 10/3![American Airlines logo]()
$511
This Southwest deal was found by Cheapflights users on 10/5. 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.
Sat 11/73:15 pm -
1 stop8h 30m
Sat 11/145:00 am -
1 stop7h 15m
Deal found 10/5![Southwest logo]()
$601
This Booking.com deal was found by Cheapflights users on 10/4. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/73:45 pm -
2 stops19h 38m
Sat 11/145:58 pm -
2 stops43h 47m
Deal found 10/4![Air Canada logo]()
$453
This United Airlines deal was found by Cheapflights users on 10/4. 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.
Wed 12/22:52 pm -
1 stop18h 53m
Sun 12/69:34 pm -
1 stop14h 16m
Deal found 10/4![United Airlines logo]()
$501
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.
Thu 12/34:05 pm -
2 stops26h 12m
Sun 12/67:05 am -
2 stops29h 35m
Deal found 10/2![Delta logo]()
$506
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/14:45 pm -
1 stop22h 28m
Thu 12/3110:05 am -
1 stop27h 40m
Deal found 10/3![Air Canada logo]()
$469
This United Airlines deal was found by Cheapflights users on 10/4. 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.
Thu 11/262:52 pm -
1 stop18h 56m
Sat 12/58:40 am -
Nonstop5h 17m
Deal found 10/4![United Airlines logo]()
$582
This Delta deal was found by Cheapflights users on 10/4. 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.
Thu 11/264:05 pm -
2 stops21h 20m
Mon 11/306:44 pm -
2 stops17h 56m
Deal found 10/4![Delta logo]()
$605
This Southwest deal was found by Cheapflights users on 10/6. 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.
Mon 11/304:40 pm -
1 stop8h 35m
Thu 12/38:50 pm -
2 stops15h 30m
Deal found 10/6![Southwest logo]()
$702
This Delta deal was found by Cheapflights users on 10/4. 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.
Wed 12/24:05 pm -
2 stops17h 54m
Sun 12/65:30 am -
1 stop7h 10m
Deal found 10/4![Delta logo]()
$605
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/303:15 pm -
2 stops19h 45m
Wed 12/25:20 am -
1 stop6h 55m
Deal found 10/2![Southwest logo]()
$712
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.
Tue 12/14:05 pm -
2 stops22h 56m
Sat 12/56:41 pm -
2 stops41h 59m
Deal found 10/2![Delta logo]()
$864
Last-minute flights from St. Maarten to ChicagoDiscover last-minute flight deals from St. Maarten to Chicago. Data last updated October 7, 2026 and is based on user searches.
Discover last-minute flight deals from St. Maarten to Chicago. Data last updated October 7, 2026 and is based on user searches.
This Booking.com deal was found by Cheapflights users on 10/4. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/73:45 pm -
2 stops19h 38m
Sat 11/145:58 pm -
2 stops43h 47m
Deal found 10/4![Air Canada logo]()
$453
This Southwest deal was found by Cheapflights users on 10/5. 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.
Sat 11/73:15 pm -
1 stop8h 30m
Sat 11/145:00 am -
1 stop7h 15m
Deal found 10/5![Southwest logo]()
$601
This Southwest deal was found by Cheapflights users on 10/4. 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 11/183:15 pm -
2 stops16h 25m
Wed 11/259:05 pm -
2 stops15h 10m
Deal found 10/4![Southwest logo]()
$570
This Delta deal was found by Cheapflights users on 10/4. 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.
Wed 11/184:05 pm -
1 stop8h 49m
Wed 11/256:00 am -
1 stop6h 40m
Deal found 10/4![Delta logo]()
$591
This Southwest deal was found by Cheapflights users on 10/6. 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 11/204:40 pm -
1 stop8h 30m
Fri 11/277:00 am -
1 stop6h 40m
Deal found 10/6![Southwest logo]()
$543
This Delta deal was found by Cheapflights users on 10/4. 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.
Thu 11/264:05 pm -
1 stop8h 49m
Sun 11/296:00 am -
1 stop6h 37m
Deal found 10/4![Delta logo]()
$491
This Delta deal was found by Cheapflights users on 10/4. 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.
Thu 11/264:05 pm -
1 stop8h 49m
Mon 11/306:44 pm -
2 stops17h 56m
Deal found 10/4![Delta logo]()
$506
This Delta deal was found by Cheapflights users on 10/4. 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.
Thu 11/264:05 pm -
1 stop8h 49m
Sat 12/56:00 am -
1 stop6h 45m
Deal found 10/4![Delta logo]()
$577
This Delta deal was found by Cheapflights users on 10/4. 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.
Thu 11/264:05 pm -
1 stop8h 49m
Fri 12/46:41 pm -
2 stops17h 30m
Deal found 10/4![Delta logo]()
$680
This Trip.com deal was found by Cheapflights users on 10/4. 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.
Mon 11/304:45 pm -
1 stop24h 53m
Wed 12/23:45 pm -
1 stop21h 00m
Deal found 10/4![Air Canada logo]()
$345
This Trip.com deal was found by Cheapflights users on 10/4. 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.
Mon 11/304:45 pm -
1 stop24h 53m
Thu 12/312:50 pm -
1 stop24h 55m
Deal found 10/4![Air Canada logo]()
$349
This Booking.com deal was found by Cheapflights users on 10/4. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/304:45 pm -
1 stop18h 23m
Fri 12/47:20 am -
2 stops29h 25m
Deal found 10/4![Air Canada logo]()
$485
One-way flights from St. Maarten to ChicagoSearch for one-way flight options from St. Maarten to Chicago. Find affordable one-way fares based on user searches. Data last updated October 7, 2026.
Search for one-way flight options from St. Maarten to Chicago. Find affordable one-way fares based on user searches. Data last updated October 7, 2026.
This Trip.com deal was found by Cheapflights users on 10/5. 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 11/123:45 pm -
1 stop30h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Air Canada logo]()
$212
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.
Mon 11/24:45 pm -
1 stop24h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![Air Canada logo]()
$217
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/33:45 pm -
2 stops27h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/3![Air Canada logo]()
$232
This Expedia deal was found by Cheapflights users on 10/4. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/164:45 pm -
1 stop24h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![Air Canada logo]()
$241
This Air Canada deal was found by Cheapflights users on 10/4. 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 11/14:45 pm -
1 stop18h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![Air Canada logo]()
$246
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 10/312:40 pm -
2 stops26h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/3![Air Canada logo]()
$249
This Travelocity deal was found by Cheapflights users on 10/6. 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.
Thu 12/103:45 pm -
1 stop25h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Air Canada logo]()
$250
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/13:45 pm -
2 stops25h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![Air Canada logo]()
$256
This Air Canada deal was found by Cheapflights users on 10/5. 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.
Fri 12/44:45 pm -
2 stops20h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Air Canada logo]()
$258
This Southwest deal was found by Cheapflights users on 10/6. 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.
Thu 1/143:35 pm -
1 stop9h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Southwest logo]()
$279
This Delta deal was found by Cheapflights users on 10/6. 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 11/104:05 pm -
1 stop8h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Delta logo]()
$291
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/53:20 pm -
1 stop8h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/3![Southwest logo]()
$316
Find flight deals from St. Maarten to Chicago
Keep the following information in mind while searching for St. Maarten to Chicago flight deals. Data was last updated October 7, 2026.
Round-trip from | $345 (Trip.com) |
|---|---|
One-way from | $212 (Trip.com) |
Good round-trip deal | $222 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from St. Maarten to Chicago 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 7, 2026.
Use the filters below to find and compare flights from St. Maarten to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Simpson BayChicago
SXM Simpson Bay Princess Juliana - MDW Chicago Midway
SXMMDW
Simpson Bay Princess Juliana
Thu 1/14
3:35 pm-10:50 pm
1 stop9h 15m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$279
Quickest round-trip
Simpson BayChicago
SXM Simpson Bay Princess Juliana - ORD Chicago O'Hare Intl
SXMORD
Simpson Bay Princess Juliana
Fri 12/18
2:10 pm-6:11 pm
Nonstop6h 01m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$280
Simpson BayChicago
SXM Simpson Bay Princess Juliana - MDW Chicago Midway
SXMMDW
Simpson Bay Princess Juliana
Thu 11/12
4:05 pm-10:54 pm
1 stop8h 49m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$291
Simpson BayChicago
SXM Simpson Bay Princess Juliana - MDW Chicago Midway
SXMMDW
Simpson Bay Princess Juliana
Fri 12/18
4:05 pm-10:54 pm
1 stop8h 49m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$291
Simpson BayChicago
SXM Simpson Bay Princess Juliana - MDW Chicago Midway
SXMMDW
Simpson Bay Princess Juliana
Thu 12/3
4:05 pm-10:54 pm
1 stop8h 49m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$291
Simpson BayChicago
SXM Simpson Bay Princess Juliana - ORD Chicago O'Hare Intl
SXMORD
Simpson Bay Princess Juliana
Sat 10/31
3:05 pm-11:57 pm
1 stop9h 52m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$291
Simpson BayChicago
SXM Simpson Bay Princess Juliana - ORD Chicago O'Hare Intl
SXMORD
Simpson Bay Princess Juliana
Wed 11/4
4:05 pm-11:57 pm
1 stop9h 52m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$291
Simpson BayChicago
SXM Simpson Bay Princess Juliana - ORD Chicago O'Hare Intl
SXMORD
Simpson Bay Princess Juliana
Tue 11/3
2:52 pm-12:01 am
1 stop11h 09m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$295
Simpson BayChicago
SXM Simpson Bay Princess Juliana - ORD Chicago O'Hare Intl
SXMORD
Simpson Bay Princess Juliana
Thu 11/5
4:05 pm-7:41 am
2 stops17h 36m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$296
Simpson BayChicago
SXM Simpson Bay Princess Juliana - ORD Chicago O'Hare Intl
SXMORD
Simpson Bay Princess Juliana
Fri 12/4
4:05 pm-10:29 am
2 stops20h 24m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$300
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SXM-ORD
SXM-MDW
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SX0-CHI
SXM-ORD
SXM-MDW
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