What is the cheapest way to get from Chicago to Kissimmee?

The cheapest way to get from Chicago to Kissimmee is to bus which costs $120 - $230 and takes 25h 26m.

What is the fastest way to get from Chicago to Kissimmee?

The fastest way to get from Chicago to Kissimmee is to fly which takes 5h 37m and costs $95 - $490.

Is there a direct bus between Chicago and Kissimmee?

No, there is no direct bus from Chicago station to Kissimmee. However, there are services departing from Chicago Bus Station and arriving at N Main St & W Cypress St via Atlanta Bus Station and Florida Mall Ave & Crystal Clear Ln. The journey, including transfers, takes approximately 25h 26m.

Is there a direct train between Chicago and Kissimmee?

Yes, there is a direct train departing from Chicago Union Station station and arriving at Kissimmee Amtrak Station station. Services depart once daily, and operate every day. The journey takes approximately 39h.

How far is it from Chicago to Kissimmee?

The distance between Chicago and Kissimmee is 1025 miles. The road distance is 1121.9 miles.

How do I travel from Chicago to Kissimmee without a car?

The best way to get from Chicago to Kissimmee without a car is to bus which takes 25h 26m and costs $120 - $230.

How long does it take to get from Chicago to Kissimmee?

It takes approximately 5h 37m to get from Chicago to Kissimmee, including transfers.

Where do I catch the Chicago to Kissimmee bus from?

Chicago to Kissimmee bus services, operated by Flixbus USA, depart from Chicago Bus Station.

Where do I catch the Chicago to Kissimmee train from?

Chicago to Kissimmee train services, operated by Amtrak, depart from Chicago Union Station.

Train, bus or fly from Chicago to Kissimmee?

The best way to get from Chicago to Kissimmee is to fly which takes 5h 37m and costs $95 - $490. Alternatively, you can bus, which costs $120 - $230 and takes 25h 26m, you could also train, which costs $280 - $440 and takes 39h.

Where does the Chicago to Kissimmee bus arrive?

Chicago to Kissimmee bus services, operated by Flixbus USA, arrive at Atlanta Bus Station.

What is the time difference between Chicago and Kissimmee?

Kissimmee is 1h ahead of Chicago. It is currently 7:11 PM in Chicago and 8:11 PM in Kissimmee.

Where does the Chicago to Kissimmee train arrive?

Chicago to Kissimmee train services, operated by Amtrak, arrive at Kissimmee Amtrak Station.

Can I drive from Chicago to Kissimmee?

Yes, the driving distance between Chicago to Kissimmee is 1122 miles. It takes approximately 19h 48m to drive from Chicago to Kissimmee.

How do I get a train ticket from Chicago to Kissimmee?

Book your Chicago to Kissimmee train tickets online with Omio.

Where can I stay near Kissimmee?

There are 9875+ hotels available in Kissimmee.

Chicago to Kissimmee - 9 ways to travel via train, plane, bus, car, and taxi

There are 9 ways to get from Chicago to Kissimmee by plane, bus (Flixbus, Greyhound), train (Amtrak), car, train, or taxi

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

Fly Chicago Midway International Airport to Orlando
best
1. Fly from Chicago Midway International Airport (MDW) to Orlando (MCO)plane MDW - MCO
5h 37m
$96–481
Fly Chicago O'Hare International Airport to Orlando
cheapest
1. Fly from Chicago O'Hare International Airport (ORD) to Orlando (MCO)plane ORD - MCO
5h 58m
$92–361
Bus
1. Take the bus from Chicago Bus Station to Atlanta Bus Stationbus FlixBus 2512 / ...
2. Take the bus from Atlanta Bus Station to Orlandobus FlixBus 2415
25h 26m
$127–227
Train (Amtrak)
1. Take the train from Chicago Union Station to Kissimmee Amtrak Stationtrain Floridian
39h
$280–440
Drive 1,115.4 mi
1. Drive from Chicago to Kissimmeecar 1,115.4 mi
19h 48m
$204–294
Train to South Bend, fly to Orlando Sanford, taxi
1. Take the train from Van Buren St. to South Bend Airporttrain
2. Fly from South Bend (SBN) to Orlando Sanford (SFB)plane SBN - SFB
3. Take the taxi from Orlando-Sanford-Airport-SFB to Kissimmeetaxi
6h 23m
$233–794
Train to General Mitchell International Airport, fly to Orlando
1. Take the train from Chicago Union Station to Milwaukeetrain
2. Fly from General Mitchell International Airport (MKE) to Orlando (MCO)plane MKE - MCO
7h 13m
$158–362
Fly Chicago Midway International Airport to Tampa, train
1. Fly from Chicago Midway International Airport (MDW) to Tampa (TPA)plane MDW - TPA
2. Take the train from Tampa to Kissimmee Amtrak Stationtrain
7h 45m
$120–581
Fly Chicago O'Hare International Airport to Tampa, train
1. Fly from Chicago O'Hare International Airport (ORD) to Tampa (TPA)plane ORD - TPA
2. Take the train from Tampa to Kissimmee Amtrak Stationtrain
8h 4m
$120–341

Chicago to Kissimmee by bus

7Weekly Buses

25h 26mAverage Duration

$127Cheapest Price

See schedules

Questions & Answers

Map of how to get from Chicago to Kissimmee.

Launch map view

Distance: 1,019.4 mi
Duration: 5h 37m

What companies run services between Chicago, IL, USA and Kissimmee, FL, USA?

Frontier Airlines and Southwest Airlines fly from Chicago Midway International Airport (MDW) to Orlando (MCO) every 3 hours. Alternatively, you can take a bus from Chicago Bus Station to N Main St & W Cypress St via Atlanta Bus Station, Orlando, and Florida Mall Ave & Crystal Clear Ln in around 25h 26m.

Airlines

Train operators

Bus operators

Other operators

Want to know more about travelling around United States

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.