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Grand Case economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Villas at Simpson Bay Resort
4.0-star property

The Villas at Simpson Bay Resort

9.2/10 Wonderful! (1,192 reviews)

Aug 29 - Sep 1

3 night stay

Chicago (CHI) to Philipsburg (SXM)

Spirit Airlines • Non-stop roundtrip • Coach
per person
found 1 day ago
The property was very nice, clean and beautiful. The beach area was very nice with huts for shade. Plenty of chairs to relax in. The pool area was cleaned everyday and not crowded. The jewelry shop owner was the nicest man. Easy to talk to with no pressure to purchase anything. Several restaurants with good food and drinks I would definitely come back to this resorts.

Reviewed on Jun 8, 2025

Simpson Bay Resort, Marina & Spa
4.0-star property

Simpson Bay Resort, Marina & Spa

9/10 Wonderful! (1,192 reviews)

Aug 27 - Sep 1

5 night stay

Chicago (CHI) to Philipsburg (SXM)

Spirit Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 15 hours ago
We love Simpson Bay Resort! Wonderful place to stay and excellent location!

Reviewed on Jul 5, 2025

Esmeralda Resort
4.0-star property

Esmeralda Resort

8.6/10 Excellent! (463 reviews)

Aug 21 - Aug 28

7 night stay

Chicago (CHI) to Philipsburg (SXM)

American Airlines • Non-stop roundtrip • Coach
per person
found 16 hours ago
The Esmeralda Resort/Spa is an ideal place for those that like a quiet, detached, peaceful, and less crowded type setting. Its situated behind a beach bar at the north end of the bay. Cabins of 4 units share their own pool, thus making it quite cozy and private to lounge in your "own pool". The restaurant is fantastic for the quality of the food and its staff. The staff were extremely helpful, friendly, and as a single traveler, they engaged in conversation but not too much so seem invasive. Do not mistake the restaurant for being low cost--it was not. It can be on the pricy end to dine there, yet well worth it. The included continental brunch, was sort of blah, as there is nothing but carbs, and more carbs to eat. A small bowl of fruit is provided, along with 2 types of cereal, teas and coffee. If eggs or meats or anything else beyond bread (too much bread) is desired, then there is a menue available for those items at a cost. I highly recommend Esmeralda and would gladly stay again.

Reviewed on Apr 7, 2025

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Grand Case first class flight packages

Price found within the past 48 hours. Click for updated prices.
Holland House Beach Hotel
4.0-star property

Holland House Beach Hotel

9.2/10 Wonderful! (1,000 reviews)

Sep 4 - Sep 8

4 night stay

Chicago (ORD) to Philipsburg (SXM)

American Airlines • Non-stop roundtrip • FirstClass
per person
found 1 day ago
great and friendly service.

Reviewed on Jun 15, 2025

The Villas at Simpson Bay Resort
4.0-star property

The Villas at Simpson Bay Resort

9.2/10 Wonderful! (1,192 reviews)

Sep 4 - Sep 8

4 night stay

Chicago (ORD) to Philipsburg (SXM)

American Airlines • Non-stop roundtrip • FirstClass
per person
found 1 day ago
The property was very nice, clean and beautiful. The beach area was very nice with huts for shade. Plenty of chairs to relax in. The pool area was cleaned everyday and not crowded. The jewelry shop owner was the nicest man. Easy to talk to with no pressure to purchase anything. Several restaurants with good food and drinks I would definitely come back to this resorts.

Reviewed on Jun 8, 2025

Hilton Vacation Club Royal Palm St. Maarten
4.0-star property

Hilton Vacation Club Royal Palm St. Maarten

9/10 Wonderful! (1,048 reviews)

Sep 4 - Sep 8

4 night stay

Chicago (ORD) to Philipsburg (SXM)

American Airlines • Non-stop roundtrip • FirstClass
per person
found 1 day ago
Loved the private beach area with umbrellas and chairs , pool area, restaurant on site with delicious breakfast and dinner options. The swim up bar was very enjoyable. The staff was sooooo friendly and our rooms were SPOTLESS. Gift shop on site was as good as going out shopping around… and the market on the premises has anything you forgot. We took family pics out on the beach one night. Only negative was the bar down the street you can hear the music late at night. But as far as this property…. BOOK IT!

Reviewed on Jun 21, 2025

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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.

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.