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Departure City: Chicago

Destination: Naples/Gulf Coast

Dates: All Dates

Change your departure city | Start a new search | All prices are based on double occupancy.

Flight + Hotel

Your dates from $201

Flight + Car

Your dates from $195

Naples/Gulf Coast, FL (via Fort Myers): Florida's Riviera More sophisticated than Florida's trendy east coast, Naples, and the diverse stretch of beaches surrounding it, please sunbathers, small tykes, and shoppers alike. Includes Flight, Hotel, Taxes & Fees	from $201 per person
Fort Myers, FL: A Timeless Classic It's what epic movies are made of, the stuff of Southern mansions and stately palms--and a river runs through it. Includes Flight, Hotel, Taxes & Fees	from $201 per person
Sanibel and Captiva Islands, FL (via Fort Myers): Sixty Shades of Sea Shells Capture someone's heart on these serene islands off Florida's Gulf coast. Includes Flight, Hotel, Taxes & Fees	from $219 per person