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

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There are 8 ways to get from Walt Disney World to Chicago by plane, bus (Flixbus, Greyhound), train (Amtrak), car, taxi, or train

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
    6h 23m
    $206–499

  2. Fly Orlando to Chicago O'Hare International Airport

    cheapest
    1. Fly from Orlando (MCO) to Chicago O'Hare International Airport (ORD)plane plane MCO - ORD
    6h 46m
    $76–609

  3. Bus

    1. Take the bus from Orlando Bus Station to Atlanta Bus Stationbus bus FlixBus N2401 / ...
    2. Take the bus from Atlanta Bus Station to Chicago Bus Stationbus bus FlixBus 2512 / ...
    25h 11m
    $177–352

  4. Train (Amtrak)

    1. Take the train from Kissimmee Amtrak Station to Chicago Union Stationtrain train Floridian
    41h 52m
    $552–1,202

  5. Drive 1,104.3 mi

    1. Drive from Walt Disney World to Chicagocar car 1,104.3 mi
    19h 43m
    $202–292

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

    1. Take the taxi from Walt Disney World 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 33m
    $272–856

  7. 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
    8h 45m
    $193–629

  8. 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
    9h 35m
    $129–514

Orlando (MCO) to Chicago Midway International Airport (MDW) flights

Calendar50Weekly Planes
Duration3h 2mAverage Duration
Ticket$83Cheapest Price
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Questions & Answers

Map of how to get from Walt Disney World to Chicago.ExpandLaunch map view
  • Distance: 1,029.5 mi
  • Duration: 6h 23m

What companies run services between Walt Disney World, FL, USA and Chicago, IL, USA?

Southwest Airlines flies from Orlando (MCO) to Chicago Midway International Airport (MDW) every 4 hours. Alternatively, you can take a vehicle from Walt Disney World to Chicago Bus Station via Topiary Ln & World Dr, N Garland Ave & W Amelia St, N John Young Pkwy & Business Center Blvd, Orlando Bus Station, and Atlanta Bus Station in around 25h 11m.

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