Cheap flight deals from Chicago (CHI) to Grand Case (SXM)

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Grand Case economy flight packages

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Simpson Bay Resort, Marina & Spa
4.0-star property

Simpson Bay Resort, Marina & Spa

9/10 Wonderful! (1,987 reviews)

Oct 8 - Oct 12

4 night stay

Chicago (CHI) to Philipsburg (SXM)

Air Canada • Non-stop • Coach

Philipsburg (SXM) to Chicago (CHI)

Southwest Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,436, price is now $790 per person
$790
per person
found 1 day ago
Great stay. Beach was nearby, food was good. Nearby clubs.

Reviewed on Sep 4, 2026

The Villas at Simpson Bay Resort
4.0-star property

The Villas at Simpson Bay Resort

9.2/10 Wonderful! (1,525 reviews)

Oct 8 - Oct 12

4 night stay

Chicago (CHI) to Philipsburg (SXM)

Air Canada • Non-stop • Coach

Philipsburg (SXM) to Chicago (CHI)

Southwest Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,646, price is now $856 per person
$856
per person
found 1 day ago

Princess Heights Luxury Boutique Condo Hotel
3.5-star property

Princess Heights Luxury Boutique Condo Hotel

9.2/10 Wonderful! (1,001 reviews)

Oct 8 - Oct 12

4 night stay

Chicago (CHI) to Philipsburg (SXM)

Air Canada • Non-stop • Coach

Philipsburg (SXM) to Chicago (CHI)

Southwest Airlines • Non-stop • Coach
Price was $1,191, price is now $866 per person
$866
per person
found 1 day ago
The property was beautiful, clean and the staff was impeccable! They put a bottle of wine in my room on my birthday. The front desk was amazing and also the housekeepers.

Reviewed on Aug 13, 2026

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More About Flying To Grand Case from Chicago

Route Information for Flights from Chicago to Grand Case

Origin Airport IATA Code
CHI
Destination Airport IATA Code
SXM
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Grand Case

If you are looking for guaranteed low prices on flights from Chicago to Grand Case, then look no further than Orbitz. Orbitz offers everything you need to plan the perfect trip—from cheap deals and bargain holiday packages to cutting-edge mobile tools.

Your Perfect Grand CaseVacation Package

Orbitz gives you access to exclusive deals and discounts on flights from Chicago to Grand Case. Mix and match hotels and Chicago to Grand Case flights to create your dream vacation. All your options are displayed at a glance with the Orbitz Matrix Display, which shows your package savings and built-in extras, such as free nights.

Stress free Searches Even on the Move

With free mobile apps for iPhone and Android, you never have to miss out on great prices on flights from Chicago to Grand Case. In a hurry? No worry—just check your flight status using m.orbtiz.com via your mobile browser or to book that exclusive hotel deal.

Don’t Forget the Car Rental

Need a car after your Chicago to Grand Case flights? Not only do you get great rental deals when you book in advance with Orbitz, we can send your flight details to the car rental company, so it knows when your flight from Chicago to Grand Case is delayed.

Low Price Guarantee

With the best deals and easy searching options, Orbitz make it easy and fun to find cheap Chicago to Grand Case flights, a great hotel, or a full vacation package. With Orbitz’s low price guarantee, you always get great discounts on air ticket prices.

Frequently asked questions

What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won't keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

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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.