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How to get fromChicago to Winter Springsby subway, plane, train, bus (Greyhound, Flixbus), train (Amtrak), or car

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There are 7 ways to get from Chicago to Winter Springs by subway, plane, train, bus (Greyhound, Flixbus), train (Amtrak), 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. Subway to Chicago Midway International Airport, fly to Orlando, train

    best
    1. Take the subway from Adams/Wabash to Midwaysubway subway
    2. Fly from Chicago Midway International Airport (MDW) to Orlando (MCO)plane plane MDW - MCO
    3. Take the train from Sand Lake Road to Longwoodtrain train
    6h 8m
    $206–503

  2. Fly Chicago O'Hare International Airport to Orlando, train

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Orlando (MCO)plane plane ORD - MCO
    2. Take the train from Sand Lake Road to Longwoodtrain train
    6h 27m
    $86–423

  3. Bus

    1. Take the bus from Chicago Bus Station to Atlanta Bus Stationbus bus Greyhound US0100
    2. Take the bus from Atlanta Bus Station to Orlando Bus Stationbus bus FlixBus N2401 / ...
    25h 13m
    $212–337

  4. Train (Amtrak)

    1. Take the train from Chicago Union Station to Winter Park Amtrak Stationtrain train Floridian
    38h 14m
    $447–1,023

  5. Drive  1,102.8 mi

    1. Drive from Chicago to Winter Springscar car 1,102.8 mi
    20h 15m
    $202–291

  6. Train to South Bend, fly to Orlando Sanford

    1. Take the train from Van Buren St. to South Bend Airporttrain train
    2. Fly from South Bend (SBN) to Orlando Sanford (SFB)plane plane SBN - SFB
    5h 37m
    $127–499

  7. Train to General Mitchell International Airport, fly to Orlando

    1. Take the train from Chicago Union Station to Milwaukeetrain train
    2. Fly from General Mitchell International Airport (MKE) to Orlando (MCO)plane plane MKE - MCO
    7h 47m
    $446–1,181

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

Calendar57Weekly Planes
Duration2h 54mAverage Duration
Ticket$120Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Winter Springs.ExpandLaunch map view
  • Distance: 1,030 mi
  • Duration: 6h 8m

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

You can take a bus from Chicago Bus Station to Winter Springs via Atlanta Bus Station and Orlando Bus Station in around 25h 13m. Alternatively, Amtrak operates a train from Chicago Union Station to Winter Park Amtrak Station once daily. Tickets cost $420–1,000 and the journey takes 37h 59m.

Airlines
Train operators
Bus operators

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