
$83 Cheap flight deals from Chicago (CHI) to Watersound (DSI)
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This Weekend's Flight Deals from Chicago to Watersound
This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Airfares from $83 One Way, $184 Round Trip from Chicago to Watersound
Prices starting at $184 for return flights and $83 for one-way flights to Watersound were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Watersound economy flight packages

Spark by Hilton Destin
Mar 18 - Mar 25
Chicago (CHI) to Fort Walton Beach (VPS)
Reviewed on Oct 11, 2025


The Henderson Beach Resort & Spa
Mar 18 - Mar 25
Chicago (CHI) to Fort Walton Beach (VPS)
Reviewed on Sep 1, 2025
More About Flying To Watersound from Chicago
Route Information for Flights from Chicago to Watersound
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | DSI |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Watersound
Great Deals on Flights From Chicago to Watersound
Spend more of your time and money at Watersound instead of sitting at your computer, searching for discount Chicago to Watersound flights. This is why Orbitz makes it easy for you to check out destinations, plan your trip, and book your air fare, hotel, car rental, and more in just one place. Our low price guarantee means that you get great deals on flights from Chicago to Watersound.
Flights That Fit Your Budget
Traveling on a budget? Not to worry if you are using Orbitz. We monitor thousands of fares to make sure we show you the best air ticket prices available for your travel dates. Besides amazing prices on Chicago to Watersound flights, we offer you great deals on hotels, vacation packages, and last-minute getaways for the perfect trip.
Orbitz customers can receive credit for frequent flyer miles and points. Simply provide your frequent flyer details when you book qualifying Chicago to Watersound flights with Orbitz.
Search for Flights from Chicago to Watersound on the Go
Orbitz offers free mobile apps for iPad, iPhone, and Android-based devices, so even the busiest trip-planner can research and book flights from Chicago to Watersound. Find cheap Chicago to Watersound flights, research local festivities and attractions, and book reservations while sitting in the salon. Orbitz will also update you on flight delays with free alerts sent to your mobile phone or email address, so you’re never left in the dark.
Flights from Chicago
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Watersound Airports
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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.



