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

Find Transport to Chicago Loop

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There are 9 ways to get from Orlando to Chicago Loop by plane, bus (Flixbus, Greyhound), 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 44m
    $204–487

  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 1m
    $74–607

  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
    24h 15m
    $177–335

  4. Train (Amtrak)

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

  5. Drive 1,107.5 mi

    1. Drive from Orlando to Chicago Loopcar car 1,107.5 mi
    19h 38m
    $203–292

  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
    6h 55m
    $112–482

  7. 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 20m
    $167–582

  8. 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 5m
    $201–671

  9. 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 Millennium Stationtrain train
    6h 7m
    $204–788

Orlando to Chicago Loop by bus

Calendar40Weekly Buses
Duration24h 15mAverage Duration
Ticket$177Cheapest Price
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Questions & Answers

Map of how to get from Orlando to Chicago Loop.ExpandLaunch map view
  • Distance: 1,019.2 mi
  • Duration: 4h 44m

What companies run services between Orlando, FL, USA and Chicago Loop, 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 Bus Station to Chicago Bus Station via Atlanta Bus Station in around 24h 15m.

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