Bluebird
Fort Myers, Florida

Private charter · MDW → RSW

Chicago to Fort Myers

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

Photo: Ebyabe · CC BY-SA 3.0

Price your flight from Chicago to Fort Myers

Trip type
1

Times are local to each departure airport.

The trip

Chicago to Fort Myers, 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 Fort Myers, 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
MDWChicagoRSWFort Myers
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 Fort Myers

Airports in Fort Myers

  • RSW

    Major airport

    Southwest Florida International Airport

    Fort Myers · KRSW

    From downtown
    9 mi
    Longest runway
    12,000 ft

  • FMY

    Commercial airport

    Page Field

    Fort Myers · KFMY

    From downtown
    3 mi
    Longest runway
    6,406 ft

  • PGD

    Commercial airport

    Punta Gorda Airport

    Punta Gorda · KPGD

    From downtown
    22 mi
    Longest runway
    7,193 ft

When you land

Things to do in Fort Myers

Fort Myers sits on the Caloosahatchee River at the heart of Southwest Florida, a fast-growing region where healthcare, construction, real estate and tourism lead the economy. Thomas Edison and Henry Ford chose the city for their winter homes, and the riverfront River District keeps a historic downtown feel with brick streets and restaurants. It is the spring training home of both the Boston Red Sox and the Minnesota Twins, and the gateway to Sanibel and Captiva, Fort Myers Beach, Cape Coral and Pine Island.

  1. 01

    Edison and Ford Winter Estates

    The neighboring winter homes of Thomas Edison and Henry Ford sit on the Caloosahatchee River, with sprawling gardens, Edison's botanical research laboratory and a museum of their inventions.

  2. 02

    Sanibel and Captiva Islands

    Across the causeway, these barrier islands are famous for shelling, with the bent-over 'Sanibel stoop' a local pastime, plus bike paths, quiet beaches and laid-back island restaurants.

  3. 03

    J.N. "Ding" Darling National Wildlife Refuge

    On Sanibel, this refuge protects mangrove estuary habitat, with a wildlife drive, paddling trails and excellent birding for roseate spoonbills, pelicans and wading birds.

  4. 04

    Fort Myers Beach

    On Estero Island, this casual beach town offers wide sand, gentle surf, dolphin cruises and boat trips into the mangroves and islands of Estero Bay.

  5. 05

    Spring Training Ballparks

    Catch the Boston Red Sox at JetBlue Park, with its replica Green Monster, or the Minnesota Twins at Hammond Stadium during Grapefruit League season in February and March.

  6. 06

    River District

    Downtown Fort Myers' historic waterfront district features brick streets, restored buildings, restaurants and galleries along the Caloosahatchee, with regular art walks and street festivals.

Explore Fort Myers charter

Questions

Chicago to Fort Myers flights

How long is a private flight from Chicago to Fort Myers?

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 Fort Myers 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), Page Field (FMY), or Punta Gorda Airport (PGD). Pick whichever is closest to where you're starting and where you're headed.

How much does a private charter from Chicago to Fort Myers 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 Fort Myers?

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

Return flight

Fort Myers to Chicago

More flights from Chicago

More flights to Fort Myers

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

Chicago to Fort Myers, 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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