$124 Cheap flight deals from Chicago (CHI) to Philipsburg (SXM)
Earn rewards on top of your airline miles with Orbitz Rewards
Many airlines offer flexible change policies
Sign up to receive text alerts about your trip
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 $124 One Way, $331 Round Trip from Chicago to Philipsburg
Prices starting at $331 for return flights and $124 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
Oct 28 - Nov 1
Chicago (CHI) to Philipsburg (SXM)
Philipsburg (SXM) to Chicago (CHI)
Reviewed on Sep 21, 2026
The Villas at Simpson Bay Resort
Oct 28 - Nov 1
Chicago (CHI) to Philipsburg (SXM)
Philipsburg (SXM) to Chicago (CHI)
La Playa Orient Bay
Oct 28 - Nov 1
Chicago (CHI) to Philipsburg (SXM)
Philipsburg (SXM) to Chicago (CHI)
Reviewed on Sep 18, 2026
Philipsburg first class flight packages
The Forest
Nov 1 - Nov 7
Chicago (CHI) to Philipsburg (SXM)
Reviewed on May 11, 2026
Sonesta Maho Beach All Inclusive Resort Casino & Spa
Nov 1 - Nov 7
Chicago (CHI) to Philipsburg (SXM)
Reviewed on Sep 21, 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
Grab great fares on Chicago to Philipsburg flights with Orbitz, your #1 source for discount international and domestic air tickets. Our cutting-edge mobile tools and great online search functionality make booking your next budget trip a breeze.
Mobile Apps for Exclusive Deals on Flights From Chicago to Philipsburg
You don’t have to sit down at a computer to find the latest flight bargains. Orbitz offers a mobile app for Android, iPhone, and tablet devices, which will keep you alert to fantastic fares, hotel discounts, and more great savings. The app gives you real-time low fares for flights from Chicago to Philipsburg and lets you book your hotel room with a few simple clicks.
Find Your Chicago to Philipsburg Flights, Car, and Hotel in One Place
Orbitz gives you the latest deals on air fares, hotels, cruises, and car rentals at up to 50% off. Booking your flights from Chicago to Philipsburg is easy whether you are using a computer, with the Orbitz mobile app, or through m.orbitz.com on your mobile device’s Web browser.
Stay Informed on Your Trip
Orbitz sends you alerts about the latest updates to your Chicago to Philipsburg flights, such as delays. Receive the updates via your email or mobile phone. Use the Orbitz app to stay updated on your flight status and baggage claim details.
Earn Miles for Flights From Chicago to Philipsburg
On qualified flights, add your frequent flyer number to your booking to get miles or points for your trip.
Flights from Chicago
- Chicago to Houston
- Chicago to Orlando
- Chicago to New York
- Chicago to Phoenix
- Chicago to Dallas
- Chicago to Los Angeles
- Chicago to New Orleans
- Chicago to Washington
- Chicago to London
- Chicago to Paris
- Chicago to Rome
- Chicago to Toronto
- Chicago to San Francisco
- Chicago to Cleveland
- Chicago to Detroit
- Chicago to Sacramento
- Chicago to Montreal
- Chicago to Kansas City
- Chicago to Atlantic City
- Chicago to Hartford
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.