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How to get fromOrlando to Chicago Union Stationby plane, bus (Greyhound, Flixbus), train (Amtrak), car, bus, or train

Find Transport to Chicago Union Station

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There are 8 ways to get from Orlando to Chicago Union Station by plane, bus (Greyhound, Flixbus), train (Amtrak), car, bus, 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
    4h 51m
    $204–497

  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 17m
    $74–607

  3. Bus

    1. Take the bus from Orlando RedCoach Station to Atlanta - Civic Center MARTA Stationbus bus Orlando–Atlanta
    2. Take the bus from Atlanta Bus Station to Chicago Bus Stationbus bus FlixBus 2512 / ...
    22h 55m
    $224–427

  4. Train (Amtrak)

    1. Take the train from Orlando to Chicago Union Stationtrain train Floridian
    38h 55m
    $550–1,200

  5. Drive 1,107.1 mi

    1. Drive from Orlando to Chicago Union Stationcar car 1,107.1 mi
    19h 38m
    $202–292

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

    1. Take the bus from Orlando Bus Station to Tampa Bus Stationbus bus
    2. Fly from Tampa (TPA) to Chicago Midway International Airport (MDW)plane plane TPA - MDW
    7h 1m
    $112–483

  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
    7h 3m
    $191–626

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

    1. Take the bus from Orlando Bus Station to Tampa Bus Stationbus bus
    2. Fly from Tampa (TPA) to Chicago O'Hare International Airport (ORD)plane plane TPA - ORD
    7h 36m
    $177–583

Orlando to Chicago Union Station by bus, subway, and foot

Calendar7Weekly Services
Duration22h 55mAverage Duration
Ticket$224Cheapest Price
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Questions & Answers

Map of how to get from Orlando to Chicago Union Station.ExpandLaunch map view
  • Distance: 1,019.3 mi
  • Duration: 4h 51m

What companies run services between Orlando, FL, USA and Chicago Union Station, IL, USA?

Southwest Airlines flies from Orlando (MCO) to Chicago Midway International Airport (MDW) every 4 hours. Alternatively, you can take a bus from Orlando RedCoach Station to Chicago Union Station via Atlanta - Civic Center MARTA Station, Civic Center Station, Garnett Station, Atlanta Bus Station, and Chicago Bus Station in around 22h 55m.

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