Private charter · MDW → ISM
Chicago to Kissimmee
998 miles. One price for the whole airplane.
Price your flight from Chicago to Kissimmee
The trip
Chicago to Kissimmee, door to door faster.
Trade about 21 hours on the road for about a short flight in the air. Bluebird flies you direct from Chicago Midway International Airport in Chicago to Kissimmee Gateway Airport in Kissimmee, 998 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
- 998 mi
- Flight
- —
- Driving
- 21 hours
- Passengers
- Up to 1
Departing Chicago
Airports in Chicago
MDW
Major airportChicago Midway International Airport
Chicago · KMDW
- From downtown
- 9 mi
- Longest runway
- 6,522 ft
ORD
Major airportChicago O'Hare International Airport
Chicago · KORD
- From downtown
- 16 mi
- Longest runway
- 13,000 ft
PWK
Commercial airportChicago Executive Airport
Chicago/Prospect Heights/Wheeling · KPWK
- From downtown
- 21 mi
- Longest runway
- 5,001 ft
GYY
Commercial airportGary/Chicago International Airport
Gary · KGYY
- From downtown
- 21 mi
- Longest runway
- 8,859 ft
Arriving Kissimmee
Airports in Kissimmee
ISM
Commercial airportKissimmee Gateway Airport
Orlando · KISM
- From downtown
- 2 mi
- Longest runway
- 6,001 ft
MCO
Major airportOrlando International Airport
Orlando · KMCO
- From downtown
- 11 mi
- Longest runway
- 12,005 ft
ORL
Commercial airportOrlando Executive Airport
Orlando · KORL
- From downtown
- 17 mi
- Longest runway
- 6,004 ft
GIF
Regional airportWinter Haven Regional Airport - Gilbert Field
Winter Haven · KGIF
- From downtown
- 27 mi
- Longest runway
- 5,005 ft
When you land
Things to do in Kissimmee
Kissimmee sits just southeast of Walt Disney World, and for many families it is the real base for a Central Florida vacation. Thousands of vacation rental homes and resorts line the US 192 corridor and communities like Celebration and ChampionsGate, making it easy for multigenerational groups to stay together near the parks. Business in Osceola County centers on tourism, hospitality, healthcare and a growing technology and research district.
- 01
Gatorland
Opened in 1949, this classic Florida attraction showcases thousands of alligators and crocodiles, with wrestling shows, a breeding-marsh boardwalk and a zipline that soars over the gators.
- 02
Walt Disney World Resort
Disney's four theme parks are just minutes from Kissimmee, along with two water parks and the Disney Springs dining, shopping and entertainment district.
- 03
Old Town Kissimmee
A retro-style entertainment district on US 192 with rides, shops and restaurants, best known for its weekly classic car cruises and shows.
- 04
Lake Tohopekaliga
Lake Toho is famous for trophy largemouth bass, with guided fishing trips, airboat tours and Kissimmee Lakefront Park along its northern shore.
- 05
Celebration
Built by Disney in the 1990s, this planned town has a walkable lakefront downtown with restaurants and shops, and seasonal events like its evening holiday snowfall.
- 06
Everglades Headwaters Airboat Tours
Airboat rides on the lakes and marshes around Kissimmee offer close-up looks at alligators, bald eagles, wading birds and wild Central Florida scenery.
Questions
Chicago to Kissimmee flights
How long is a private flight from Chicago to Kissimmee?
About a short flight in a private jet, for 998 miles direct. Driving the same trip takes about 21 hours.
Which airports do flights from Chicago to Kissimmee use?
You can depart from Chicago Midway International Airport (MDW), Chicago O'Hare International Airport (ORD), or Chicago Executive Airport (PWK) and arrive at Kissimmee Gateway Airport (ISM), Orlando International Airport (MCO), or Orlando Executive Airport (ORL). Pick whichever is closest to where you're starting and where you're headed.
How much does a private charter from Chicago to Kissimmee 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 Kissimmee?
Yes. Choose round trip when you search, and pick your return date and time. Flights from Kissimmee back to Chicago are priced the same way.
Return flight
Kissimmee to Chicago
More flights from Chicago
More flights to Kissimmee
Explore Chicago private charter and Kissimmee private charter, airports and things to do. Arriving at Kissimmee Gateway Airport (ISM).
Chicago to Kissimmee, 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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