$105 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.

Sun, Jan 4 - Wed, Jan 21
MDW
Midway Intl.
ECP
Northwest Florida Beaches Intl.
$284 Roundtrip, found 2 days ago
$284
Roundtrip
found 2 days ago
Select Delta flight, departing Sun, Jan 4 from Midway Intl. to Northwest Florida Beaches Intl., returning Wed, Jan 21, priced at $284 found 2 days ago
Sun, Jan 4 - Fri, Jan 16
ORD
O'Hare Intl.
ECP
Northwest Florida Beaches Intl.
$304 Roundtrip, found 2 days ago
$304
Roundtrip
found 2 days ago
Select Delta flight, departing Sun, Jan 4 from O'Hare Intl. to Northwest Florida Beaches Intl., returning Fri, Jan 16, priced at $304 found 2 days ago
Sat, Jan 3 - Tue, Jan 6
RFD
Greater Rockford
ECP
Northwest Florida Beaches Intl.
$312 Roundtrip, found 6 days ago
$312
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sat, Jan 3 from Greater Rockford to Northwest Florida Beaches Intl., returning Tue, Jan 6, priced at $312 found 6 days ago

Airfares from $105 One Way, $202 Round Trip from Chicago to Watersound

Prices starting at $202 for return flights and $105 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.

Mon, May 11 - Sat, May 16
MDW
Chicago
ECP
Panama City
$202 Roundtrip, found 2 days ago
$202
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Mon, May 11 from Chicago to Panama City, returning Sat, May 16, priced at $202 found 2 days ago
Sun, Mar 8 - Mon, Mar 16
ORD
Chicago
ECP
Panama City
$209 Roundtrip, found 2 days ago
$209
Roundtrip
found 2 days ago
Select United flight, departing Sun, Mar 8 from Chicago to Panama City, returning Mon, Mar 16, priced at $209 found 2 days ago
Mon, May 11 - Sat, May 16
MDW
Chicago
ECP
Panama City
$212 Roundtrip, found 2 days ago
$212
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, May 11 from Chicago to Panama City, returning Sat, May 16, priced at $212 found 2 days ago
Mon, May 11 - Sat, May 16
MDW
Chicago
ECP
Panama City
$218 Roundtrip, found 2 days ago
$218
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Mon, May 11 from Chicago to Panama City, returning Sat, May 16, priced at $218 found 2 days ago
Sun, May 10 - Fri, May 15
MDW
Chicago
ECP
Panama City
$219 Roundtrip, found 1 day ago
$219
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sun, May 10 from Chicago to Panama City, returning Fri, May 15, priced at $219 found 1 day ago

Watersound economy flight packages

Price found within the past 48 hours. Click for updated prices.
Sandestin Golf and Beach Resort
4.0-star property

Sandestin Golf and Beach Resort

7.8/10 Good! (3,841 reviews)

Feb 15 - Feb 20

5 night stay

Chicago (CHI) to Fort Walton Beach (VPS)

Southwest Airlines • Non-stop roundtrip • Coach
Price was $996, price is now $694 per person
$694
per person
found 17 hours ago
Motorcycle not welcome, front desk lady rude ,no housekeeping until 3 days 🙄 i request clean sheets never get it

Reviewed on Apr 28, 2025

The Henderson Beach Resort & Spa
5.0-star property

The Henderson Beach Resort & Spa

9.2/10 Wonderful! (1,000 reviews)

Feb 15 - Feb 20

5 night stay

Chicago (CHI) to Fort Walton Beach (VPS)

Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,255, price is now $847 per person
$847
per person
found 17 hours ago
⸻ We expected the hotel to be more family-friendly. The kids club was always closed and it was impossible to reach anyone there. There weren’t many kids’ menu options and not a lot of activities for children. On the positive side, the hotel is very beautiful, clean, and the staff is friendly. However, the price feels very high compared to the overall value received.

Reviewed on Sep 1, 2025

Bay Club of Sandestin
3.5-star property

Bay Club of Sandestin

9/10 Wonderful! (154 reviews)

Feb 15 - Feb 20

5 night stay

Chicago (CHI) to Fort Walton Beach (VPS)

Southwest Airlines • Non-stop roundtrip • Coach
Price was $887, price is now $711 per person
$711
per person
found 17 hours ago
The rooms are gorgeous and well kept and the view is to die for!

Reviewed on Dec 3, 2021

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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

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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.