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How to get fromThe Villages to Chicagoby shuttle, plane, bus (Amtrak, Flixbus, Greyhound), taxi, train, car, or bus

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There are 10 ways to get from The Villages to Chicago by shuttle, plane, bus (Amtrak, Flixbus, Greyhound), taxi, train, car, or bus

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Shuttle to Orlando, fly to Chicago Midway International Airport

    best
    1. Take a shuttle bus from Lake Sumter Depot to MCO Airport - Terminal Ashuttle bus
    2. Fly from Orlando (MCO) to Chicago Midway International Airport (MDW)plane plane MCO - MDW
    6h 11m
    $230–517

  2. Shuttle to Orlando, fly to Chicago O'Hare International Airport

    cheapest
    1. Take a shuttle bus from Lake Sumter Depot to MCO Airport - Terminal Ashuttle bus
    2. Fly from Orlando (MCO) to Chicago O'Hare International Airport (ORD)plane plane MCO - ORD
    6h 29m
    $135–457

  3. Bus

    1. Take the bus from The Villages-Lady Lake Amtrak Bus Stop to Jacksonvillebus bus
    2. Take the bus from Jacksonville to Atlanta Bus Stationbus bus
    3. Take the bus from Atlanta Bus Station to Chicago Bus Stationbus bus
    28h 54m

  4. Taxi, train

    1. Take the taxi from The Villages to Delandtaxi taxi
    2. Take the train from Deland to Chicago Union Stationtrain train Floridian
    39h 3m
    $1,007–1,626

  5. Drive  1,053.1 mi

    1. Drive from The Villages to Chicagocar car 1,053.1 mi
    18h 57m
    $193–278

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

    1. Take a shuttle bus from Lake Sumter Depot to Tampa International Airport - Red Terminalshuttle bus
    2. Fly from Tampa (TPA) to Chicago Midway International Airport (MDW)plane plane TPA - MDW
    6h 58m
    $154–473

  7. Shuttle to Tampa, fly to Chicago O'Hare International Airport

    1. Take a shuttle bus from Lake Sumter Depot to Tampa International Airport - Red Terminalshuttle bus
    2. Fly from Tampa (TPA) to Chicago O'Hare International Airport (ORD)plane plane TPA - ORD
    7h 26m
    $144–373

  8. Bus to Jacksonville, fly to Chicago Midway International Airport

    1. Take the bus from The Villages-Lady Lake Amtrak Bus Stop to Jacksonvillebus bus
    2. Fly from Jacksonville (JAX) to Chicago Midway International Airport (MDW)plane plane JAX - MDW
    9h 51m

  9. Shuttle to Orlando, fly to General Mitchell International Airport, train

    1. Take a shuttle bus from Lake Sumter Depot to MCO Airport - Terminal Ashuttle bus
    2. Fly from Orlando (MCO) to General Mitchell International Airport (MKE)plane plane MCO - MKE
    3. Take the train from Milwaukee to Chicago Union Stationtrain train
    8h 31m
    $495–1,241

  10. Bus to Jacksonville, fly to Chicago O'Hare International Airport

    1. Take the bus from The Villages-Lady Lake Amtrak Bus Stop to Jacksonvillebus bus
    2. Fly from Jacksonville (JAX) to Chicago O'Hare International Airport (ORD)plane plane JAX - ORD
    10h 26m

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

Calendar80Weekly Planes
Duration2h 52mAverage Duration
Ticket$87Cheapest Price
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Comparing Your Travel Options

Map of how to get from The Villages to Chicago.ExpandLaunch map view
  • Distance: 1,069.3 mi
  • Duration: 6h 11m

What companies run services between The Villages, FL, USA and Chicago, IL, USA?

You can take a bus from The Villages-Lady Lake Amtrak Bus Stop to Chicago Bus Station via Jacksonville, Amtrak Station, JRTC Bay H, Jacksonville, and Atlanta Bus Station in around 28h 54m.

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