Bluebird
Naples, Florida

Private charter · MDW → RSW

Chicago to Naples

1,107 miles. One price for the whole airplane.

Photo: Franz Stellbrink · CC BY 3.0

Price your flight from Chicago to Naples

Trip type
1

Times are local to each departure airport.

The trip

Chicago to Naples, door to door faster.

Trade about 23½ hours on the road for about a short flight in the air. Bluebird flies you direct from Chicago Midway International Airport in Chicago to Southwest Florida International Airport in Naples, 1,107 miles in a private jet with two pilots up front. Need a different size of aircraft? We'll source one sized for the trip. The price is for the whole aircraft, with every fee and tax shown before you book.

Distance
1,107 mi
Flight
—
Driving
23½ hours
Passengers
Up to 1
MDWChicagoRSWNaples
MDW → RSW1,107 miles direct

Departing Chicago

Airports in Chicago

  • MDW

    Major airport

    Chicago Midway International Airport

    Chicago · KMDW

    From downtown
    9 mi
    Longest runway
    6,522 ft

  • ORD

    Major airport

    Chicago O'Hare International Airport

    Chicago · KORD

    From downtown
    16 mi
    Longest runway
    13,000 ft

  • PWK

    Commercial airport

    Chicago Executive Airport

    Chicago/Prospect Heights/Wheeling · KPWK

    From downtown
    21 mi
    Longest runway
    5,001 ft

  • GYY

    Commercial airport

    Gary/Chicago International Airport

    Gary · KGYY

    From downtown
    21 mi
    Longest runway
    8,859 ft

Arriving Naples

Airports in Naples

  • RSW

    Major airport

    Southwest Florida International Airport

    Fort Myers · KRSW

    From downtown
    28 mi
    Longest runway
    12,000 ft

  • APF

    Commercial airport

    Naples Municipal Airport

    Naples · KAPF

    From downtown
    2 mi
    Longest runway
    6,600 ft

  • MRK

    Regional airport

    Marco Island Executive Airport

    Marco Island · KMKY

    From downtown
    12 mi
    Longest runway
    5,000 ft

When you land

Things to do in Naples

Naples is a Gulf Coast town built around leisure done well: dozens of golf courses, calm turquoise water, long sunset beaches and a walkable downtown along Fifth Avenue South and Third Street South. The city draws a large seasonal population each winter, many from the Midwest and Northeast, along with a growing number of professionals who now live here year-round and run businesses or investment portfolios from home.

  1. 01

    Naples Beaches

    Naples' public beaches, from Lowdermilk Park to the historic pier at the foot of 12th Avenue South, offer soft white sand, calm Gulf water and famously colorful sunsets.

  2. 02

    Fifth Avenue South and Third Street South

    Downtown's two signature districts offer sidewalk cafes, galleries and boutiques, with a popular Saturday morning farmers market on Third Street South.

  3. 03

    Naples Botanical Garden

    Themed gardens representing the tropics of Florida, the Caribbean, Brazil and Asia spread across the grounds, with water lilies, orchids and a restored native preserve.

  4. 04

    Corkscrew Swamp Sanctuary

    Audubon's sanctuary northeast of town protects one of the largest remaining old-growth bald cypress forests in North America, explored along a 2.25-mile boardwalk.

  5. 05

    Delnor-Wiggins Pass State Park

    A barrier-island park with a wide, natural beach, good shelling, sea turtle nesting in summer and fishing at the pass where the Cocohatchee River meets the Gulf.

  6. 06

    Ten Thousand Islands

    South of Naples, boat and kayak tours explore this maze of mangrove islands, with chances to see dolphins, manatees and shorebirds, often departing from Marco Island or Everglades City.

Explore Naples charter

Questions

Chicago to Naples flights

How long is a private flight from Chicago to Naples?

About a short flight in a private jet, for 1,107 miles direct. Driving the same trip takes about 23½ hours.

Which airports do flights from Chicago to Naples use?

You can depart from Chicago Midway International Airport (MDW), Chicago O'Hare International Airport (ORD), or Chicago Executive Airport (PWK) and arrive at Southwest Florida International Airport (RSW), Naples Municipal Airport (APF), or Marco Island Executive Airport (MRK). Pick whichever is closest to where you're starting and where you're headed.

How much does a private charter from Chicago to Naples cost?

The price depends on the date, departure time, aircraft and where the airplane is positioned. Enter your trip above to see an instant price for the whole airplane, with every tax and fee included.

Can I book a round trip between Chicago and Naples?

Yes. Choose round trip when you search, and pick your return date and time. Flights from Naples back to Chicago are priced the same way.

Return flight

Naples to Chicago

More flights from Chicago

More flights to Naples

Explore Chicago private charter and Naples private charter, airports and things to do. Arriving at Southwest Florida International Airport (RSW).

Chicago to Naples, on your schedule

Choose your departure time and see a price for the whole aircraft. Bring up to 1 passengers for the same price.

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