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How to get fromWinter Park to Chicagoby plane, bus (Flixbus, Greyhound), train (Amtrak), car, or train

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There are 9 ways to get from Winter Park to Chicago by plane, bus (Flixbus, Greyhound), train (Amtrak), car, 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
    5h 21m
    $206–490

  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
    5h 45m
    $76–610

  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 Greyhound US0100
    26h 11m
    $177–352

  4. Train (Amtrak)

    1. Take the train from Winter Park Amtrak Station to Chicago Union Stationtrain train Floridian
    38h 38m
    $550–1,200

  5. Drive 1,110.8 mi

    1. Drive from Winter Park to Chicagocar car 1,110.8 mi
    19h 47m
    $203–293

  6. Fly Orlando Sanford to South Bend, train

    1. Fly from Orlando Sanford (SFB) to South Bend (SBN)plane plane SFB - SBN
    2. Take the train from South Bend Airport to Van Buren St.train train
    5h 59m
    $193–774

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

    1. Take the train from Winter Park Amtrak Station to Tampatrain train
    2. Fly from Tampa (TPA) to Chicago Midway International Airport (MDW)plane plane TPA - MDW
    8h 16m
    $135–525

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

    1. Take the train from Winter Park Amtrak Station to Tampatrain train
    2. Fly from Tampa (TPA) to Chicago O'Hare International Airport (ORD)plane plane TPA - ORD
    8h 48m
    $190–625

  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 45m
    $204–679

Winter Park to Chicago by bus

Calendar40Weekly Buses
Duration26h 11mAverage Duration
Ticket$177Cheapest Price
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Questions & Answers

Map of how to get from Winter Park to Chicago.ExpandLaunch map view
  • Distance: 1,030.1 mi
  • Duration: 5h 21m

What companies run services between Winter Park, 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 bus from W Morse Blvd & S New York Ave to Chicago Bus Station via N Garland Ave & W Amelia St, N John Young Pkwy & Business Center Blvd, Orlando Bus Station, and Atlanta Bus Station in around 26h 11m.

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