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Trailways Bus Tickets
from Kissimmee, FL to Chicago, IL

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Overview

About buses from Kissimmee, FL to Chicago, IL

Buses from Kissimmee, FL to Chicago, IL travel the 1006mi (1619.00km) journey, taking approximately 1d, 9h, 18m. Usually, there are 2 buses operating per day. While the average ticket price for this journey is around $215.96, you can find the cheapest bus tickets for as low as $196.46.

  • Distance
    1006mi (1619.00km)
  • Average trip duration
  • Average bus ticket price
    $215.96
  • Trips per day
    2
  • Top Carriers
    FlixBus

Bus Station Information for Chicago, IL

Chicago (95th & Dan Ryan)

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Chicago, IL 60628

Curbside Stop
Address
95th & Dan Ryan 
Chicago, IL 60628
Phone Number
(800) 858-8555
More Detailsabout Chicago (95th & Dan Ryan) Curbside Stop

Chicago (Cumberland Avenue)

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Chicago, IL 60631

Curbside Stop
Address
5800 N Cumberland Ave 
Chicago, IL 60631
Phone Number
(800) 858-8555
More Detailsabout Chicago (Cumberland Avenue) Curbside Stop

Chicago (Bus Station)

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Chicago, IL 60607

24 Hours
Bus Station
Address
630 West Harrison Street 
Chicago, IL 60607
Phone Number
(800) 858-8555
More Detailsabout Chicago (Bus Station) Bus Station

Chicago (Amtrak Union Station)

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Chicago, IL 60606

Curbside Stop
Address
225 S. Canal St. 
Chicago, IL 60606
Phone Number
(800) 858-8555
More Detailsabout Chicago (Amtrak Union Station) Curbside Stop

City InformationforKissimmee, FL

Gearing up for a memorable journey? Hop on a bus to Kissimmee, FL, where a mix of magic and warmth awaits. This sunny town is more than a gateway to Orlando's famed theme parks; it is a destination overflowing with charm and adventure. Whether you’re drawn to the region for thrills or relaxation, Kissimmee’s got you covered.

Dive into excitement at the area’s renowned amusement parks, just a stone's throw away. But before you dash off to rollercoasters and fairytale castles, take a moment to explore Kissimmee's own attractions. You might find yourself gliding through the Florida Everglades on an exhilarating airboat tour, surrounded by lush landscapes and rich wildlife. If you’re craving a slower pace, a leisurely walk in the historic downtown offers a chance to soak up local culture with its charming shops and eateries boasting delicious Southern staples.

Kissimmee's lively energy makes every visit feel like a celebration, gently urging you to plan your next escape. So go ahead, grab those bus tickets, and let Kissimmee envelop you in its welcoming embrace.

City InformationforChicago, IL

There’s so much to see in the Windy City, you’ll be booking your next bus to Chicago before your trip is over. No matter the season, there’s plenty to do, from lounging on lakeside beaches in the summer to ice skating in Millennium Park.

Chicago’s famous for its dogs and its deep dish, if you’re looking for eats. Museums dot the map, including The Art Institute of Chicago, Field Museum, and Griffin Museum of Science and Industry. Catch a game if your sport’s in season – Bulls or Bears, Cubs or White Sox.

If you ask a local – which we always do – an Architecture Tour is on the don’t miss list. And if you’re on a budget, just go for a stroll on the Riverwalk, Navy Pier, or by “the bean” - Millennium Park’s famed Cloud Gate sculpture.

Whatever mood strikes you, Chi-town's got something to keep you busy.

Scenic photo of Chicago, ILScenic photo of Chicago, ILScenic photo of Chicago, IL
Scenic photo of Chicago, IL
Scenic photo of Chicago, IL
Scenic photo of Chicago, IL

Frequently Asked Questions about the Bus Ride

Experience a smooth bus ride from Kissimmee to Chicago. Buses depart from Kissimmee to Chicago 2 times per day. Prices start at $196.46. Check our website for our bus tickets to Chicago.