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

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Grand Case economy flight packages

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Princess Heights Luxury Boutique Condo Hotel
3.5-star property

Princess Heights Luxury Boutique Condo Hotel

9.2/10 Wonderful! (1,003 reviews)

Jul 14 - Jul 17

3 night stay

Chicago (CHI) to Philipsburg (SXM)

Southwest Airlines • Non-stop roundtrip • Coach
Price was $861, price is now $626 per person
$626
per person
found 1 day ago
The room was spacious, clean and had adequate storage. The kitchenette was properly outfitted and they gave us a few complimentary drinks, The place was very quiet and private.

Reviewed on Nov 26, 2025

Simpson Bay Resort, Marina & Spa
4.0-star property

Simpson Bay Resort, Marina & Spa

9/10 Wonderful! (1,749 reviews)

Jul 14 - Jul 17

3 night stay

Chicago (CHI) to Philipsburg (SXM)

Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,319, price is now $652 per person
$652
per person
found 1 day ago
Nice beach, nice staff. Only gripe is charging to use the gym - come on, that’s cheap

Reviewed on Mar 7, 2026

Coral Beach Club Villas & Marina
4.0-star property

Coral Beach Club Villas & Marina

9.2/10 Wonderful! (114 reviews)

Jul 14 - Jul 21

7 night stay

Chicago (CHI) to Philipsburg (SXM)

Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,773, price is now $1,940 per person
$1,940
per person
found 1 day ago
The property was nice. The staff was great as well. The sister property (Oyster bay resort) needs to upgrade some of their facilities. The gym is very small and lackluster on both properties and the pool needs a major renovation. We had a dishwasher issue that forced us to cancel some plans one night but it was eventually fixed. Cleaning could have been better on the first day of our stay, found old bread under the bed from a previous stay. Nice stay overall but improvements could be made to make the stay more enjoyable.

Reviewed on Mar 22, 2023

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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.