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 Santa Rosa Island
The cheapest prices found with in the last 7 days for return flights were $122 and $65 for one-way flights to Santa Rosa Island for the period specified. Prices and availability are subject to change. Additional terms apply.
Tue, Jul 9 - Wed, Jul 24
ORD
O'Hare Intl.
PNS
Pensacola Intl.
$122 Roundtrip, found 2 days ago
$122
Roundtrip
found 2 days ago
Tue, Jul 9 - Wed, Jul 10
MDW
Midway Intl.
PNS
Pensacola Intl.
$148 Roundtrip, found 3 days ago
$148
Roundtrip
found 3 days ago
Sat, Sep 7 - Wed, Sep 11
ORD
O'Hare Intl.
PNS
Pensacola Intl.
$189 Roundtrip, found 15 hours ago
$189
Roundtrip
found 15 hours ago
More to explore for Chicago to Santa Rosa Island
Other Flights to Santa Rosa Island
- Chicago to Santa Rosa Island
- Newark to Santa Rosa Island
- Phoenix to Santa Rosa Island
- Omaha to Santa Rosa Island
- Washington to Santa Rosa Island
- Detroit to Santa Rosa Island
- Boston to Santa Rosa Island
- Minneapolis - St. Paul to Santa Rosa Island
- Dallas to Santa Rosa Island
- New York to Santa Rosa Island
- Houston to Santa Rosa Island
- Kansas City to Santa Rosa Island
- Louisville to Santa Rosa Island
- Baltimore to Santa Rosa Island
- Philadelphia to Santa Rosa Island
- Orlando to Santa Rosa Island
- Atlanta to Santa Rosa Island
- Cleveland to Santa Rosa Island
- Austin to Santa Rosa Island
Most Popular
Flights
Flights from Houston to DelawareFlights from Boston to TulumFlights from Detroit to AmsterdamFlights from Pittsburgh to ClearwaterFlights from Houston to San Miguel de AllendeFlights from Los Angeles to TamarindoFlights from Salt Lake City to HonoluluFlights from St. Petersburg - Clearwater to Key WestFlights from Seattle to Las VegasFlights from Portland to Las VegasFlights from Pittsburgh to St. PetersburgFlights from Fort Wayne to DestinFlights from Miami to TulumFlights from Atlanta to Las VegasFlights from Des Moines to BanffFlights from Seattle to AnaheimFlights from New York to Boca RatonFlights from Chicago to New YorkFlights from Houston to GatlinburgFlights from New York to Paradise IslandFlights from Raleigh to Punta GordaFlights from Boston to Clearwater BeachFlights from Seattle to OrickFlights from Sacramento to MauiFlights from Dallas to Bora BoraFlights from New York to San Miguel de AllendeFlights from Houston to Las VegasFlights from Portland to AnaheimFlights from Dallas to AnaheimFlights from Atlanta to Taormina