$107 Cheap flight deals from Chicago (CHI) to Santa Rosa Beach (VPS)

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This Weekend's Flight Deals from Chicago to Santa Rosa Beach

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.

Sat, Jan 3 - Sat, Jan 10
MDW
Midway Intl.
ECP
Northwest Florida Beaches Intl.
$281 Roundtrip, found 4 hours ago
$281
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Sat, Jan 3 from Midway Intl. to Northwest Florida Beaches Intl., returning Sat, Jan 10, priced at $281 found 4 hours ago
Sat, Jan 3 - Sat, Jan 10
ORD
O'Hare Intl.
ECP
Northwest Florida Beaches Intl.
$282 Roundtrip, found 4 hours ago
$282
Roundtrip
found 4 hours ago
Select Delta flight, departing Sat, Jan 3 from O'Hare Intl. to Northwest Florida Beaches Intl., returning Sat, Jan 10, priced at $282 found 4 hours ago
Sat, Jan 3 - Tue, Jan 6
RFD
Greater Rockford
ECP
Northwest Florida Beaches Intl.
$312 Roundtrip, found 4 days ago
$312
Roundtrip
found 4 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 4 days ago
Sat, Jan 3 - Sat, Jan 10
ORD
O'Hare Intl.
VPS
Northwest Florida Regional
$347 Roundtrip, found 5 days ago
$347
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Sat, Jan 3 from O'Hare Intl. to Northwest Florida Regional, returning Sat, Jan 10, priced at $347 found 5 days ago

Airfares from $107 One Way, $209 Round Trip from Chicago to Santa Rosa Beach

Prices starting at $209 for return flights and $107 for one-way flights to Santa Rosa Beach were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Mar 8 - Mon, Mar 16
ORD
Chicago
ECP
Panama City
$209 Roundtrip, found 3 hours ago
$209
Roundtrip
found 3 hours ago
Select United flight, departing Sun, Mar 8 from Chicago to Panama City, returning Mon, Mar 16, priced at $209 found 3 hours ago
Mon, May 4 - Fri, May 8
MDW
Chicago
ECP
Panama City
$219 Roundtrip, just found
$219
Roundtrip
just found
Select Southwest Airlines flight, departing Mon, May 4 from Chicago to Panama City, returning Fri, May 8, priced at $219 just found
Wed, Apr 1 - Wed, Apr 8
MDW
Chicago
ECP
Panama City
$219 Roundtrip, found 6 days ago
$219
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Wed, Apr 1 from Chicago to Panama City, returning Wed, Apr 8, priced at $219 found 6 days ago
Wed, Apr 1 - Wed, Apr 8
ORD
Chicago
ECP
Panama City
$219 Roundtrip, found 6 days ago
$219
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Apr 1 from Chicago to Panama City, returning Wed, Apr 8, priced at $219 found 6 days ago
Fri, May 1 - Thu, May 7
ORD
Chicago
ECP
Panama City
$229 Roundtrip, just found
$229
Roundtrip
just found
Select Delta flight, departing Fri, May 1 from Chicago to Panama City, returning Thu, May 7, priced at $229 just found

Santa Rosa Beach 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)

Jan 29 - Feb 1

3 night stay

Chicago (CHI) to Fort Walton Beach (VPS)

American Airlines • Non-stop roundtrip • Coach
Price was $563, price is now $471 per person
$471
per person
found 1 day 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)

Jan 29 - Feb 1

3 night stay

Chicago (CHI) to Fort Walton Beach (VPS)

American Airlines • Non-stop roundtrip • Coach
Price was $855, price is now $635 per person
$635
per person
found 1 day 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)

Jan 29 - Feb 1

3 night stay

Chicago (CHI) to Fort Walton Beach (VPS)

American Airlines • Non-stop roundtrip • Coach
Price was $671, price is now $565 per person
$565
per person
found 1 day 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 Santa Rosa Beach from Chicago

Route Information for Flights from Chicago to Santa Rosa Beach

Origin Airport IATA Code
CHI
Destination Airport IATA Code
VPS
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Santa Rosa Beach

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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.