Chicago to Santa Rosa Island Flights (CHI-VPS) from $35

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Selected fares from Chicago to Santa Rosa Island

The cheapest prices found with in the last 7 days for return flights were $93 and $35 for one-way flights to Santa Rosa Island for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Wed, Sep 11 - Tue, Sep 17
ORD
O'Hare Intl.
PNS
Pensacola Intl.
$93 Roundtrip, found 6 hours ago
$93
Roundtrip
found 6 hours ago
Select Spirit Airlines flight, departing Wed, Sep 11 from O'Hare Intl. to Pensacola Intl., returning Tue, Sep 17, priced at $93 found 6 hours ago
Frontier Airlines
Tue, Jun 11 - Wed, Jun 12
MDW
Midway Intl.
PNS
Pensacola Intl.
$145 Roundtrip, found 6 days ago
$145
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Tue, Jun 11 from Midway Intl. to Pensacola Intl., returning Wed, Jun 12, priced at $145 found 6 days ago
Delta
Tue, Sep 10 - Sat, Sep 14
ORD
O'Hare Intl.
PNS
Pensacola Intl.
$176 Roundtrip, found 6 hours ago
$176
Roundtrip
found 6 hours ago
Select Delta flight, departing Tue, Sep 10 from O'Hare Intl. to Pensacola Intl., returning Sat, Sep 14, priced at $176 found 6 hours ago

Save more with Santa Rosa Island Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Hotel Effie Sandestin, Autograph Collection

Hotel Effie Sandestin, Autograph Collection

4 out of 5
per person
Jun 24 - Jun 28
found 20 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Fort Walton Beach (VPS)
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