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

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Grand Case economy flight packages

Price found within the past 48 hours. Click for updated prices.
Simpson Bay Resort, Marina & Spa
4.0-star property

Simpson Bay Resort, Marina & Spa

9/10 Wonderful! (1,899 reviews)

Sep 4 - Sep 7

3 night stay

Chicago (CHI) to Philipsburg (SXM)

Southwest Airlines • Non-stop roundtrip • Coach
Price was $1,335, price is now $784 per person
$784
per person
found 3 hours ago

The Morgan Resort Spa Village
4.0-star property

The Morgan Resort Spa Village

9/10 Wonderful! (2,296 reviews)

Sep 17 - Sep 21

4 night stay

Chicago (CHI) to Philipsburg (SXM)

Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,685, price is now $1,069 per person
$1,069
per person
found 1 day ago
Cold AC.

Reviewed on Jul 28, 2026

Coral Beach Club Villas & Marina
4.0-star property

Coral Beach Club Villas & Marina

9.2/10 Wonderful! (118 reviews)

Aug 28 - Sep 4

7 night stay

Chicago (CHI) to Philipsburg (SXM)

Delta • Non-stop • Coach

Philipsburg (SXM) to Chicago (CHI)

Southwest Airlines • Non-stop • Coach
Save 100% on your flight
Price was $3,049, price is now $2,119 per person
$2,119
per person
found 2 hours ago
The condo and property was clean and well decorated and maintained. We had an awesome stay and will return.

Reviewed on Jul 19, 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

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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.