$230+ Cheap flights from St. Maarten to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/30. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — CHI
Sep 3 — Sep 101
Round-trip
1 adult, Economy
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Find cheap flights from St. Maarten to Chicago 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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from St. Maarten to Chicago
Cheapest
Best
Last-minute
One-way
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 August 4, 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 August 4, 2026.
This Flysmarter deal was found by Cheapflights users on 8/1. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:00 pm
SXM
- ORD
2 stops14h 44m
Air Canada
Fri 9/258:40 pm
ORD
- SXM
1 stop19h 20m
Air Canada
Deal found 8/1![Air Canada logo]()
$391
This Air Canada deal was found by Cheapflights users on 8/2. 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.
Wed 11/254:45 pm
SXM
- ORD
1 stop18h 38m
Air Canada
Tue 12/18:50 pm
ORD
- SXM
1 stop16h 55m
Air Canada
Deal found 8/2![Air Canada logo]()
$433
This Priceline deal was found by Cheapflights users on 7/31. 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 11/252:20 pm
SXM
- ORD
1 stop11h 08m
Multiple Airlines
Tue 12/18:50 pm
ORD
- SXM
1 stop16h 55m
Multiple Airlines
Deal found 7/31![Multiple Airlines logo]()
$496
This Southwest deal was found by Cheapflights users on 7/31. 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 9/43:05 pm
SXM
- MDW
1 stop8h 40m
Southwest
Sun 9/68:50 pm
MDW
- SXM
2 stops16h 15m
Southwest
Deal found 7/31![Southwest logo]()
$503
This Air Canada deal was found by Cheapflights users on 7/31. 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.
Thu 11/263:45 pm
SXM
- ORD
2 stops23h 26m
Air Canada
Wed 12/22:00 pm
ORD
- SXM
2 stops22h 45m
Air Canada
Deal found 7/31![Air Canada logo]()
$549
This Air Canada deal was found by Cheapflights users on 7/31. 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.
Thu 11/263:45 pm
SXM
- ORD
2 stops23h 26m
Air Canada
Tue 12/14:30 pm
ORD
- SXM
1 stop21h 15m
Air Canada
Deal found 7/31![Air Canada logo]()
$554
This Southwest deal was found by Cheapflights users on 8/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/191:55 pm
SXM
- MDW
1 stop8h 05m
Southwest
Fri 9/255:00 am
MDW
- SXM
1 stop8h 05m
Southwest
Deal found 8/1![Southwest logo]()
$566
This Delta deal was found by Cheapflights users on 8/1. 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.
Sat 9/193:18 pm
SXM
- MDW
2 stops18h 49m
Delta
Fri 9/257:01 pm
MDW
- SXM
2 stops17h 52m
Delta
Deal found 8/1![Delta logo]()
$658
This Delta deal was found by Cheapflights users on 8/2. 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.
Fri 9/43:18 pm
SXM
- MDW
1 stop8h 18m
Delta
Sun 9/66:05 am
MDW
- SXM
1 stop6h 48m
Delta
Deal found 8/2![Delta logo]()
$741
This Mytrip deal was found by Cheapflights users on 8/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:00 pm
SXM
- MDW
3 stops16h 07m
Multiple Airlines
Fri 9/253:20 pm
MDW
- SXM
2 stops17h 05m
Multiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$980
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 August 4, 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 August 4, 2026.
This Air Canada deal was found by Cheapflights users on 8/1. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:00 pm
SXM
- ORD
1 stop16h 00m
Air Canada
Fri 9/255:35 pm
ORD
- SXM
1 stop22h 25m
Air Canada
Deal found 8/1![Air Canada logo]()
$398
This Priceline deal was found by Cheapflights users on 7/31. 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 11/252:20 pm
SXM
- ORD
1 stop11h 08m
Multiple Airlines
Tue 12/13:45 pm
ORD
- SXM
2 stops22h 00m
Multiple Airlines
Deal found 7/31![Multiple Airlines logo]()
$499
This Southwest deal was found by Cheapflights users on 8/2. 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.
Fri 9/43:05 pm
SXM
- MDW
1 stop8h 40m
Southwest
Sun 9/65:50 pm
MDW
- SXM
2 stops19h 15m
Southwest
Deal found 8/2![Southwest logo]()
$503
This Delta deal was found by Cheapflights users on 8/1. 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.
Sat 9/193:18 pm
SXM
- MDW
2 stops18h 49m
Delta
Fri 9/257:01 pm
MDW
- SXM
2 stops17h 52m
Delta
Deal found 8/1![Delta logo]()
$658
This American Airlines deal was found by Cheapflights users on 8/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/42:22 pm
SXM
- ORD
1 stop11h 13m
American Airlines
Sun 9/68:53 pm
ORD
- SXM
1 stop15h 49m
American Airlines
Deal found 8/2![American Airlines logo]()
$665
This Air Canada deal was found by Cheapflights users on 8/2. 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.
Wed 11/254:45 pm
SXM
- ORD
1 stop18h 38m
Air Canada
Tue 12/18:50 pm
ORD
- SXM
1 stop16h 55m
Air Canada
Deal found 8/2![Air Canada logo]()
$433
This Southwest deal was found by Cheapflights users on 8/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/191:55 pm
SXM
- MDW
1 stop8h 05m
Southwest
Fri 9/255:00 am
MDW
- SXM
1 stop8h 05m
Southwest
Deal found 8/1![Southwest logo]()
$566
This Delta deal was found by Cheapflights users on 7/31. 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 9/43:18 pm
SXM
- MDW
1 stop8h 18m
Delta
Sun 9/66:05 am
MDW
- SXM
1 stop6h 48m
Delta
Deal found 7/31![Delta logo]()
$841
This Mytrip deal was found by Cheapflights users on 8/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:00 pm
SXM
- MDW
3 stops16h 07m
Multiple Airlines
Fri 9/253:20 pm
MDW
- SXM
2 stops17h 05m
Multiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$980
Last-minute flights from St. Maarten to ChicagoDiscover last-minute flight deals from St. Maarten to Chicago. Data last updated August 4, 2026 and is based on user searches.
Discover last-minute flight deals from St. Maarten to Chicago. Data last updated August 4, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 7/31. 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 9/43:05 pm
SXM
- MDW
1 stop8h 40m
Southwest
Sun 9/68:50 pm
MDW
- SXM
2 stops16h 15m
Southwest
Deal found 7/31![Southwest logo]()
$503
This Kiwi.com deal was found by Cheapflights users on 8/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/41:35 pm
SXM
- ORD
1 stop10h 52m
Multiple Airlines
Sat 9/512:44 am
ORD
- SXM
1 stop11h 06m
Multiple Airlines
Deal found 8/2![Multiple Airlines logo]()
$641
This American Airlines deal was found by Cheapflights users on 8/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/42:22 pm
SXM
- ORD
1 stop11h 13m
American Airlines
Sun 9/68:53 pm
ORD
- SXM
1 stop15h 49m
American Airlines
Deal found 8/2![American Airlines logo]()
$665
This Delta deal was found by Cheapflights users on 8/2. 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.
Fri 9/43:18 pm
SXM
- MDW
1 stop8h 18m
Delta
Sun 9/66:05 am
MDW
- SXM
1 stop6h 48m
Delta
Deal found 8/2![Delta logo]()
$741
This Flysmarter deal was found by Cheapflights users on 8/1. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:00 pm
SXM
- ORD
2 stops14h 44m
Air Canada
Fri 9/258:40 pm
ORD
- SXM
1 stop19h 20m
Air Canada
Deal found 8/1![Air Canada logo]()
$391
This Southwest deal was found by Cheapflights users on 8/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/191:55 pm
SXM
- MDW
1 stop8h 05m
Southwest
Fri 9/255:00 am
MDW
- SXM
1 stop8h 05m
Southwest
Deal found 8/1![Southwest logo]()
$566
This Delta deal was found by Cheapflights users on 8/1. 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.
Sat 9/193:18 pm
SXM
- MDW
2 stops18h 49m
Delta
Fri 9/257:01 pm
MDW
- SXM
2 stops17h 52m
Delta
Deal found 8/1![Delta logo]()
$658
This Mytrip deal was found by Cheapflights users on 8/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:00 pm
SXM
- MDW
3 stops16h 07m
Multiple Airlines
Fri 9/253:20 pm
MDW
- SXM
2 stops17h 05m
Multiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$980
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 August 4, 2026.
Search for one-way flight options from St. Maarten to Chicago. Find affordable one-way fares based on user searches. Data last updated August 4, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 7/31. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/301:35 pm
SXM
- ORD
1 stop11h 09m
JetBlue
Deal found 7/31![JetBlue logo]()
$230
This JetBlue deal was found by Cheapflights users on 7/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/271:42 pm
SXM
- ORD
1 stop11h 02m
JetBlue
Deal found 7/30![JetBlue logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/289:35 am
SXM
- ORD
3 stops30h 49m
Multiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$240
This Travelocity deal was found by Cheapflights users on 8/1. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/312:40 pm
SXM
- ORD
2 stops31h 41m
Air Canada
Deal found 8/1![Air Canada logo]()
$246
This Travelocity deal was found by Cheapflights users on 8/2. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/16:00 pm
SXM
- ORD
1 stop23h 58m
Air Canada
Deal found 8/2![Air Canada logo]()
$252
This Air Canada deal was found by Cheapflights users on 8/2. 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.
Sun 10/253:45 pm
SXM
- ORD
2 stops20h 22m
Air Canada
Deal found 8/2![Air Canada logo]()
$254
This Air Canada deal was found by Cheapflights users on 8/1. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/303:45 pm
SXM
- ORD
2 stops27h 35m
Air Canada
Deal found 8/1![Air Canada logo]()
$256
This Air Canada deal was found by Cheapflights users on 8/1. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/283:45 pm
SXM
- ORD
2 stops24h 07m
Air Canada
Deal found 8/1![Air Canada logo]()
$259
This Air Canada deal was found by Cheapflights users on 8/1. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/36:00 pm
SXM
- ORD
2 stops27h 12m
Air Canada
Deal found 8/1![Air Canada logo]()
$260
This Southwest deal was found by Cheapflights users on 8/2. 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.
Fri 8/213:05 pm
SXM
- MDW
1 stop8h 35m
Southwest
Deal found 8/2![Southwest logo]()
$333
This Southwest deal was found by Cheapflights users on 8/2. 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.
Sun 10/253:05 pm
SXM
- MDW
2 stops19h 05m
Southwest
Deal found 8/2![Southwest logo]()
$340
This Southwest deal was found by Cheapflights users on 8/2. 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.
Sat 11/73:20 pm
SXM
- MDW
1 stop8h 20m
Southwest
Deal found 8/2![Southwest logo]()
$354
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 August 4, 2026.
Round-trip from | $391 (Flysmarter) |
|---|---|
One-way from | $230 (Cheapflightsfares) |
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 2,558,603 searches. Data last updated August 4, 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 - ORD
SXMORD
Simpson Bay Princess Juliana
Sat 9/19
6:00 pm-9:00 am
1 stop16h 00m
Chicago O'Hare Intl
Fri 9/25
5:35 pm-5:00 pm
1 stop22h 25m
$398
Simpson BayChicago
SXM - ORD
SXMORD
Simpson Bay Princess Juliana
Wed 11/25
4:45 pm-9:23 am
1 stop18h 38m
Chicago O'Hare Intl
Tue 12/1
8:50 pm-3:45 pm
1 stop16h 55m
$433
Simpson BayChicago
SXM - ORD
SXMORD
Simpson Bay Princess Juliana
Wed 11/25
2:20 pm-11:28 pm
1 stop11h 08m
Chicago O'Hare Intl
Tue 12/1
3:45 pm-3:45 pm
2 stops22h 00m
$499
Simpson BayChicago
SXM - MDW
SXMMDW
Simpson Bay Princess Juliana
Fri 9/4
3:05 pm-10:45 pm
1 stop8h 40m
Chicago Midway
Sun 9/6
5:50 pm-2:05 pm
2 stops19h 15m
$503
Simpson BayChicago
SXM - MDW
SXMMDW
Simpson Bay Princess Juliana
Sat 9/19
1:55 pm-9:00 pm
1 stop8h 05m
Chicago Midway
Fri 9/25
5:00 am-2:05 pm
1 stop8h 05m
$566
Simpson BayChicago
SXM - MDW
SXMMDW
Simpson Bay Princess Juliana
Sat 9/19
3:18 pm-9:07 am
2 stops18h 49m
Chicago Midway
Fri 9/25
7:01 pm-1:53 pm
2 stops17h 52m
$658
Simpson BayChicago
SXM - ORD
SXMORD
Simpson Bay Princess Juliana
Fri 9/4
2:22 pm-12:35 am
1 stop11h 13m
Chicago O'Hare Intl
Sun 9/6
8:53 pm-1:42 pm
1 stop15h 49m
$665
Quickest round-trip
Simpson BayChicago
SXM - MDW
SXMMDW
Simpson Bay Princess Juliana
Fri 9/4
3:18 pm-10:36 pm
1 stop8h 18m
Chicago Midway
Sun 9/6
6:05 am-1:53 pm
1 stop6h 48m
$841
Simpson BayChicago
SXM - MDW
SXMMDW
Simpson Bay Princess Juliana
Sat 9/19
6:00 pm-9:07 am
3 stops16h 07m
Chicago Midway
Fri 9/25
3:20 pm-9:25 am
2 stops17h 05m
$980
Cheapest one-way
Simpson BayChicago
SXM - ORD
SXMORD
Simpson Bay Princess Juliana
Fri 8/28
1:42 pm-11:44 pm
1 stop11h 02m
$232
Showing 1-10 of 28 resultsSorted by cheapest first
Best time to book a flight from St. Maarten to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from St. Maarten with our price prediction graph.
SXM-ORD
SXM-MDW
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 St. Maarten to Chicago
SX0-CHI
SXM-ORD
SXM-MDW
No data available for this route at this time. Please check back soon.
Related info for your journey
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