What is the best way to travel?

Flight is the fastest; train is the most scenic.

It is a major city; exercise standard urban safety precautions.

Kissimmee

Chicago

Train Flight

Kissimmee to Chicago

Updated: 28 May 2026

The journey from Kissimmee to Chicago covers approximately 1,900 kilometers. The most practical way to travel is by flying from Orlando International Airport (MCO) to Chicago O'Hare (ORD) or Midway (MDW). Alternatively, you can take an Amtrak train from the Orlando station for a long, scenic journey. This route connects the sunshine of Florida to the vibrant, urban landscape of Chicago.

Total Distance: Driving distance 1,900 km, Air distance 1,600 km.

Fastest Way

Flight is the fastest method to reach Chicago.

Cheapest Way

Flight is usually the most cost-effective and fastest method.

Compare Kissimmee to Chicago Routes

	Train Connecting	Flight Direct
Duration	30 hours	3 hours
Avg Price	$150 - $350	$150 - $450
Operator	Amtrak	United Airlines
Route	Orlando to Chicago Union Station.	MCO to ORD/MDW.
Tip	The train journey requires a transfer in Washington D.C.	Book flights in advance for the best prices.

Travel Tips

Public Transit
Use the CTA 'L' train system to navigate the city efficiently.
Airport Transit
Use the CTA Blue or Orange lines to get from the airport to downtown.
Flight Travel
Arrive at MCO 2 hours before departure.
Weather
Chicago weather can be extreme; check the forecast.
Planning
Book tickets and reservations in advance for popular attractions.