
$182 Cheap flight deals from Chicago (CHI) to Philipsburg (SXM)
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This Weekend's Flight Deals from Chicago to Philipsburg
This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Airfares from $182 One Way, $423 Round Trip from Chicago to Philipsburg
Prices starting at $423 for return flights and $182 for one-way flights to Philipsburg were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Philipsburg economy flight packages

Princess Heights Luxury Boutique Condo Hotel
Dec 21 - Dec 24
Chicago (CHI) to Philipsburg (SXM)
Reviewed on Oct 24, 2026


Philipsburg business class flight packages

Princess Heights Luxury Boutique Condo Hotel
Dec 30 - Jan 3
Chicago (ORD) to Philipsburg (SXM)
Philipsburg (SXM) to Chicago (ORD)
Reviewed on Oct 24, 2026

The Atrium Beach Resort and Spa, an Ascend Collection Resort
Dec 30 - Jan 3
Chicago (ORD) to Philipsburg (SXM)
Reviewed on Nov 5, 2026

More About Flying To Philipsburg from Chicago
Route Information for Flights from Chicago to Philipsburg
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | SXM |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Philipsburg
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- Hostels in Sint Maarten
- Houseboats in Sint Maarten
- Resorts in Sint Maarten
- Villas in Sint Maarten
- Maho Reef Hotels
- Lower Prince's Quarter Hotels
- Cupecoy Hotels
- Pelican Key Hotels
- Hotels near Guana Bay Beach
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- Oyster Pond Hotels
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- Car rental Simpson Bay
- Ace New Zealand Rental Cars in Sint Maarten
- Ace Rental Cars in Sint Maarten
- Car rental Sint Maarten
- Mex Rent A Car Rental Cars in Sint Maarten
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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.
Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.
Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.



