$139 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 $139 One Way, $353 Round Trip from Chicago to Philipsburg
Prices starting at $353 for return flights and $139 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
Simpson Bay Resort, Marina & Spa
Sep 21 - Sep 28
Chicago (CHI) to Philipsburg (SXM)
Philipsburg (SXM) to Chicago (CHI)
Reviewed on Aug 18, 2026
Holland House Beach Hotel
Sep 21 - Sep 28
Chicago (CHI) to Philipsburg (SXM)
Philipsburg (SXM) to Chicago (CHI)
More About Flying To Philipsburg from Chicago
Route Information for Flights from Chicago to Philipsburg
Origin Airport IATA Code | CHI |
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Destination Airport IATA Code | SXM |
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Latest Flight Arrival |
Chicago to Philipsburg
Great Deals on Flights From Chicago to Philipsburg
Spend more of your time and money at Philipsburg instead of sitting at your computer, searching for discount Chicago to Philipsburg flights. This is why Orbitz makes it easy for you to check out destinations, plan your trip, and book your air fare, hotel, car rental, and more in just one place. Our low price guarantee means that you get great deals on flights from Chicago to Philipsburg.
Flights That Fit Your Budget
Traveling on a budget? Not to worry if you are using Orbitz. We monitor thousands of fares to make sure we show you the best air ticket prices available for your travel dates. Besides amazing prices on Chicago to Philipsburg flights, we offer you great deals on hotels, vacation packages, and last-minute getaways for the perfect trip.
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Flights from Chicago
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More Destinations
- B&B in Cole Bay
- Guest Houses in Cole Bay
- Hostels in Cole Bay
- Cole Bay Hotels
- Houseboats in Cole Bay
- Villas in Cole Bay
- Cay Bay Hill Hotels
- Hotels near Casino Royale
- Hotels near Maho Beach
- Hotels near American University of the Caribbean
- Hotels near Hollywood Casino
- Hotels near Mullet Bay Beach
- Hotels near Kim Sha Beach
- Villas in Lowlands
- Condo Rentals in Simpson Bay
- Guest Houses in Simpson Bay
- Simpson Bay Hotels
- Resorts in Simpson Bay
- Sucker Garden Hotels
- Hotels near Cupecoy Beach
- Hotels near Flamingo Beach
- Adventure Hotels in Sint Maarten
- Arcade Hotels in Sint Maarten
- Beach Resorts & in Sint Maarten
- Casino Resorts & in Sint Maarten
- Business Hotels in Sint Maarten
- Hotels with a Lazy River in Sint Maarten
- Hotels with Bar in Sint Maarten
- Hotels with Childcare in Sint Maarten
- Hotels with Free Airport Shuttle in Sint Maarten
- Hotels with Hot Tubs in Sint Maarten
- Romantic Getaways & Hotels in Sint Maarten
- Waterpark Hotels & Resorts in Sint Maarten
- Sint Maarten Hotels
- Apartments in Sint Maarten
- B&B in Sint Maarten
- Condo Rentals in Sint Maarten
- Cottages in Sint Maarten
- Extended Stay Hotels in Sint Maarten
- 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
- Hotels near Princess Juliana Intl.
- Hotels near Paradise Plaza
- Oyster Pond Hotels
- Flights from Cole Bay
- Flights from Cay Bay Hill
- Flights from Atlanta to Simpson Bay
- Flights from Houston to Simpson Bay
- Flights from Panama City to Simpson Bay
- Flights from Syracuse to Simpson Bay
- Flights from Simpson Bay
- Flights to Sint Maarten
- Flights from Sint Maarten
- Flights to Maho Reef
- Flights to Lower Prince's Quarter
- Flights from Lower Prince's Quarter
- Flights to Cupecoy
- Flights from Beacon Hill
- Flights from Princess Juliana Intl.
- Flights from New York (JFK) to Philipsburg (SXM)
- Flights to Cul de Sac
- 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
- Nextcar Rental Cars in Sint Maarten
- Rent A Wreck Rental Cars in Sint Maarten
- Top Rent a Car Rental Cars in Sint Maarten
- Rental cars Princess Juliana Intl. airport
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.