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

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There are 9 ways to get from Orlando to Chicago 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 41m
    $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 5m
    $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 1,106.6 mi

    1. Drive from Orlando to Chicagocar car 1,106.6 mi
    19h 37m
    $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
    6h 52m
    $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 24m
    $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 Van Buren St.train train
    6h 4m
    $204–788

Orlando to Chicago 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.ExpandLaunch map view
  • Distance: 1,018.5 mi
  • Duration: 4h 41m

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

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