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

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! (1,560 reviews)

Dec 13 - Dec 18

5 night stay

Chicago (CHI) to Philipsburg (SXM)

Southwest Airlines • Non-stop • Coach

Philipsburg (SXM) to Chicago (CHI)

American Airlines • Non-stop • Coach
Price was $2,055, price is now $1,143 per person
$1,143
per person
found 17 hours ago

Simpson Bay Resort, Marina & Spa
4.0-star property

Simpson Bay Resort, Marina & Spa

9/10 Wonderful! (2,074 reviews)

Nov 20 - Nov 27

7 night stay

Chicago (CHI) to Philipsburg (SXM)

Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,652, price is now $1,525 per person
$1,525
per person
found 1 day ago
The energy that comes from the staff is extremely rude. You don’t feel very welcomed the parking and the buildings are very confusing. There’s no labeling. The map is really confusing to read. Also there’s no labeling for elevators so I had to carry my luggage up the stairs to the sixth floor and again there’s no one to help to guide you to the elevator either there’s no valet the guy that store is a scam artist.

Reviewed on Oct 21, 2026

Princess Heights Luxury Boutique Condo Hotel
3.5-star property

Princess Heights Luxury Boutique Condo Hotel

9.2/10 Wonderful! (1,001 reviews)

Nov 20 - Nov 27

7 night stay

Chicago (CHI) to Philipsburg (SXM)

Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,338, price is now $1,423 per person
$1,423
per person
found 1 day ago

Don't see what you're looking for?
See all available trips from Chicago to Grand Case
View all trips

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

Smart business means on-the-spot travel planning at budget prices. Orbitz On-the-Go can help by using cutting-edge mobile tools and guaranteed low prices. Orbitz On-the-Go is your go-to for bargain flights from Chicago to Grand Case, and discount Chicago to Grand Case flights.

Business Development

Boosting sales with multiple presentations within a day or week? Then easily book cheap domestic flights from Chicago to Grand Case. Are you expanding into emerging markets? Find low-fare deals on international Chicago to Grand Case flights. Orbitz On-the-Go mobile apps keep it simple.

Continuing Education

Successful business people know that keeping your edge in business means staying in training. Find a low-cost air ticket for your next workshop with Orbitz flights from Chicago to Grand Case. Move to the head of the seminar with Orbitz On-the-Go’s guaranteed low prices on Chicago to Grand Case flights.

Budget Planning

Orbitz allows you to focus on the income, while we reduce your expenses with guaranteed low prices. Your bottom line is bound to improve with our bargain flights from Chicago to Grand Case and discount Chicago to Grand Case flights. Watch your business thrive.

Time Management

Time is money, and Orbitz On-the-Go saves both. Our cutting-edge mobile tools make business travel planning quick and easy, even for same-day reservations. It’s not unusual for our clients to save big on same-day tickets for Chicago to {destination.name} flights. Free alerts keep you on time with flight, gate and baggage updates, plus other time-saving features.

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.

More Destinations

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.