Rome2Rio

How to get fromChicago Midway Airport (MDW) to Kissimmeeby plane, bus (Flixbus, Greyhound), train (Amtrak), train, or car

Find Transport to Kissimmee

See all options

There are 6 ways to get from Chicago Midway Airport (MDW) to Kissimmee by plane, bus (Flixbus, Greyhound), train (Amtrak), train, or car

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

  1. Fly Chicago Midway International Airport to Orlando

    best
    1. Fly from Chicago Midway International Airport (MDW) to Orlando (MCO)plane plane MDW - MCO
    3h 59m
    $209–490

  2. Fly Chicago O'Hare International Airport to Orlando

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Orlando (MCO)plane plane ORD - MCO
    6h 31m
    $78–516

  3. Bus

    1. Take the bus from Chicago to Atlanta Bus Stationbus bus FlixBus 2512
    2. Take the bus from Atlanta Bus Station to Orlandobus bus FlixBus 2415
    27h 38m
    $178–338

  4. Train (Amtrak)

    1. Take the train from Chicago Union Station to Kissimmee Amtrak Stationtrain train Floridian
    40h 45m
    $506–1,208

  5. Fly Chicago Midway International Airport to Tampa, train

    1. Fly from Chicago Midway International Airport (MDW) to Tampa (TPA)plane plane MDW - TPA
    2. Take the train from Tampa to Kissimmee Amtrak Stationtrain train
    6h 10m
    $159–455

  6. Drive 1,116 mi

    1. Drive from Chicago Midway Airport (MDW) to Kissimmeecar car 1,116 mi
    19h 54m
    $204–295

Chicago Midway Airport (MDW) to Kissimmee by bus

Calendar6Weekly Buses
Duration27h 38mAverage Duration
Ticket$178Cheapest Price
See schedules

Questions & Answers

Map of how to get from Chicago Midway Airport (MDW) to Kissimmee.ExpandLaunch map view
  • Distance: 1,009.1 mi
  • Duration: 3h 59m

What companies run services between Chicago Midway Airport (MDW), USA and Kissimmee, FL, USA?

Southwest Airlines flies from Chicago Midway International Airport (MDW) to Orlando (MCO) every 4 hours. Alternatively, you can take a bus from Midway Orange Line Station to N Main St & W Cypress St via Ashland & 59th Street, 95th Red Line Station, Chicago, Atlanta Bus Station, Orlando, and Florida Mall in around 27h 38m.

Airlines
Train operators
Bus 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.

Related travel guides

Need to know: Greyhound

Read the travel guideNeed to know: Greyhound

More Questions & Answers