
$115 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 $115 One Way, $209 Round Trip from Chicago to Watersound
Prices starting at $209 for return flights and $115 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

Bay Club of Sandestin
Nov 6 - Nov 11
Chicago (CHI) to Fort Walton Beach (VPS)
Fort Walton Beach (VPS) to Chicago (CHI)
Reviewed on Dec 3, 2021

The Henderson Beach Resort & Spa
Nov 6 - Nov 11
Chicago (CHI) to Fort Walton Beach (VPS)
Fort Walton Beach (VPS) to Chicago (CHI)
Reviewed on Sep 1, 2025

WaterColor Inn & Resort
Nov 7 - Nov 10
Chicago (CHI) to Fort Walton Beach (VPS)
Fort Walton Beach (VPS) to Chicago (CHI)
Reviewed on Jan 23, 2023
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 | 811 mi |
Direct Flight Airlines | United Airlines |
Earliest Flight Arrival | 6:10PM UTC |
Latest Flight Arrival | 6:10PM UTC |
Chicago to Watersound
Orbitz combines guaranteed low prices with cutting-edge mobile tools for travel from Chicago to Watersound to give you a travel experience that is second to none.
Bargain Travel at Your Fingertips
Orbitz provides the cheapest fares from Chicago to Watersound. When reserving your flight you can mix and match a range of low cost airlines for you departing and returning domestic or international flights. This way you can travel on a budget while selecting the flights that suit your schedule.
Modern Tools for Fast-Paced Travel
Orbitz makes use of the latest technology to ensure that you are always kept up-to-date on the status of your Chicago to Watersound flights. Through easy-to-use mobile Android and iPhone apps you can book low cost flights from Chicago to Watersound and choose a range of cheap hotels to stay in.
Enjoy Stress-Free Travel with Flight Alerts
Once you have booked your flights from Chicago to Watersound on Orbitz you will always be kept informed of any changes to your flight. When you opt into Orbitz’s free email and SMS alerts on your Chicago to Watersound flights you can ask Orbitz to send the flight details to up to 6 other contacts, so keeping your family and business team informed is a cinch.
Frequent Flyer Program
For loyal Orbitz customers who fly from Chicago to Watersound the chance to join our frequent flyer program is an added bonus. Simply log-on to your online account and input your frequent flyer number for future flights.
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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.