Chicago to Santa Rosa Island Flights (CHI-VPS) from $45

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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 $97 and $45 for one-way flights to Santa Rosa Island for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Tue, Jun 4 - Wed, Jun 12
ORD
O'Hare Intl.
PNS
Pensacola Intl.
$97 Roundtrip, found 4 days ago
$97
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Tue, Jun 4 from O'Hare Intl. to Pensacola Intl., returning Wed, Jun 12, priced at $97 found 4 days ago
Frontier Airlines
Tue, May 21 - Wed, May 22
MDW
Midway Intl.
PNS
Pensacola Intl.
$108 Roundtrip, found 5 days ago
$108
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Tue, May 21 from Midway Intl. to Pensacola Intl., returning Wed, May 22, priced at $108 found 5 days ago
Delta
Tue, Sep 10 - Tue, Sep 24
ORD
O'Hare Intl.
VPS
Northwest Florida Regional
$196 Roundtrip, found 2 days ago
$196
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Sep 10 from O'Hare Intl. to Northwest Florida Regional, returning Tue, Sep 24, priced at $196 found 2 days ago

Save more with Santa Rosa Island Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
The Cabins at Gulf State Park

The Cabins at Gulf State Park

3 out of 5
per person
Jun 13 - Jun 20
Roundtrip non-stop flight included
Chicago (ORD) to Pensacola (PNS)
Eagle Cottages at Gulf State Park

Eagle Cottages at Gulf State Park

3 out of 5
Save 100% on your flight
per person
Jun 13 - Jun 20
Roundtrip non-stop flight included
Chicago (ORD) to Pensacola (PNS)
Village by the Gulf

Village by the Gulf

3 out of 5
per person
Jun 13 - Jun 20
Roundtrip non-stop flight included
Chicago (ORD) to Pensacola (PNS)
Pirate's Nest

Pirate's Nest

4 out of 5
per person
Jun 13 - Jun 20
Roundtrip non-stop flight included
Chicago (ORD) to Pensacola (PNS)
Beachside Resort Hotel

Beachside Resort Hotel

2 out of 5
per person
Jun 13 - Jun 20
Roundtrip non-stop flight included
Chicago (ORD) to Pensacola (PNS)
Hotel Indigo Orange Beach - Gulf Shores, an IHG Hotel

Hotel Indigo Orange Beach - Gulf Shores, an IHG Hotel

3.5 out of 5
per person
Jun 13 - Jun 20
Roundtrip non-stop flight included
Chicago (ORD) to Pensacola (PNS)
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