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How to get fromKissimmee to Chicagoby plane, bus (Flixbus, Greyhound), train (Amtrak), car, train or taxi

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There are 9 ways to get from Kissimmee to Chicago 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.

  1. Fly Orlando to Chicago Midway International Airport

    best
    1. Fly from Orlando (MCO) to Chicago Midway International Airport (MDW)plane plane MCO - MDW
    5h 17m
    $86–420

  2. Bus

    1. Take the bus from Orlando to Atlanta Bus Stationbus bus FlixBus 2415
    2. Take the bus from Atlanta Bus Station to Chicago Bus Stationbus bus FlixBus 2512 / ...
    26h 11m
    $127–242

  3. Train (Amtrak)

    1. Take the train from Kissimmee Amtrak Station to Chicago Union Stationtrain train Floridian
    39h 39m
    $240–550

  4. Drive 1,120.8 mi

    1. Drive from Kissimmee to Chicagocar car 1,120.8 mi
    19h 42m
    $205–296

  5. Fly Orlando to Chicago O'Hare International Airport

    1. Fly from Orlando (MCO) to Chicago O'Hare International Airport (ORD)plane plane MCO - ORD
    5h 38m
    $91–360

  6. Train to Tampa, fly to Chicago Midway International Airport

    1. Take the train from Kissimmee Amtrak Station to Tampatrain train
    2. Fly from Tampa (TPA) to Chicago Midway International Airport (MDW)plane plane TPA - MDW
    7h 28m
    $109–494

  7. Taxi to Orlando Sanford, fly to South Bend, train

    1. Take the taxi from Kissimmee to Orlando-Sanford-Airport-SFBtaxi taxi
    2. Fly from Orlando Sanford (SFB) to South Bend (SBN)plane plane SFB - SBN
    3. Take the train from South Bend Airport to Van Buren St.train train
    6h 30m
    $227–688

  8. Train to Tampa, fly to Chicago O'Hare International Airport

    1. Take the train from Kissimmee Amtrak Station to Tampatrain train
    2. Fly from Tampa (TPA) to Chicago O'Hare International Airport (ORD)plane plane TPA - ORD
    7h 51m
    $119–344

  9. Fly Orlando to General Mitchell International Airport, train

    1. Fly from Orlando (MCO) to General Mitchell International Airport (MKE)plane plane MCO - MKE
    2. Take the train from Milwaukee to Chicago Union Stationtrain train
    7h 43m
    $158–365

Kissimmee to Chicago by bus

Calendar7Weekly Buses
Duration26h 11mAverage Duration
Ticket$127Cheapest Price
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Questions & Answers

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

Frontier Airlines, Southwest Airlines, and Delta fly from Orlando (MCO) to Chicago Midway International Airport (MDW) every 2 hours. Alternatively, you can take a bus from N Main St & E Cypress St to Chicago Bus Station via Florida Mall Ave & Crystal Clear Ln, Orlando, and Atlanta Bus Station in around 26h 11m.

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