Chicago to Destin Flights (CHI-VPS) from $90

Wander Wisely with exceptional service, 24/7 support

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Selected fares from Chicago to Destin

The cheapest prices found with in the last 7 days for return flights were $210 and $90 for one-way flights to Destin for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sat, Aug 31 - Tue, Sep 3
ORD
O'Hare Intl.
VPS
Northwest Florida Regional
$210 Roundtrip, just found
$210
Roundtrip
just found
Select American Airlines flight, departing Sat, Aug 31 from O'Hare Intl. to Northwest Florida Regional, returning Tue, Sep 3, priced at $210 just found
American Airlines
Tue, Jun 11 - Tue, Jun 25
ORD
O'Hare Intl.
VPS
Northwest Florida Regional
$239 Roundtrip, found 1 day ago
$239
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Jun 11 from O'Hare Intl. to Northwest Florida Regional, returning Tue, Jun 25, priced at $239 found 1 day ago
American Airlines
Mon, Apr 29 - Fri, May 3
ORD
O'Hare Intl.
VPS
Northwest Florida Regional
$241 Roundtrip, found 22 hours ago
$241
Roundtrip
found 22 hours ago
Select American Airlines flight, departing Mon, Apr 29 from O'Hare Intl. to Northwest Florida Regional, returning Fri, May 3, priced at $241 found 22 hours ago

Save more with Destin Flight + Hotel packages

Palms Resort #1516 Full 2 Bedroom

Palms Resort #1516 Full 2 Bedroom

2 out of 5
per person
May 26 - May 30
Roundtrip non-stop flight included
Chicago (ORD) to Fort Walton Beach (VPS)
Don't see what you're looking for?
See all available trips from Chicago to Destin
View all trips
Prices and availability subject to change. Additional terms may apply.