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How to get fromChicago to The Villagesby plane, shuttle, bus (Greyhound, Flixbus, Amtrak), train, taxi, car, or bus

Find Transport to The Villages

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There are 9 ways to get from Chicago to The Villages by plane, shuttle, bus (Greyhound, Flixbus, Amtrak), train, taxi, 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. Fly Chicago Midway International Airport to Orlando, shuttle

    best
    1. Fly from Chicago Midway International Airport (MDW) to Orlando (MCO)plane plane MDW - MCO
    2. Take a shuttle bus from MCO Airport - Terminal B to Spanish Springsshuttle bus
    6h 57m
    $222–520

  2. Fly Chicago O'Hare International Airport to Orlando, shuttle

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Orlando (MCO)plane plane ORD - MCO
    2. Take a shuttle bus from MCO Airport - Terminal B to Spanish Springsshuttle bus
    7h 24m
    $152–480

  3. Bus

    1. Take the bus from Chicago Bus Station to Atlanta Bus Stationbus bus
    2. Take the bus from Atlanta Bus Station to Jacksonvillebus bus
    3. Take the bus from Jacksonville to The Villages-Lady Lake Amtrak Bus Stopbus bus
    28h 56m

  4. Train, taxi

    1. Take the train from Chicago Union Station to Delandtrain train Floridian
    2. Take the taxi from Deland to The Villagestaxi taxi
    38h 20m
    $1,023–1,546

  5. Drive  1,051.7 mi

    1. Drive from Chicago to The Villagescar car 1,051.7 mi
    18h 57m
    $186–269

  6. Fly Chicago Midway International Airport to Tampa, shuttle

    1. Fly from Chicago Midway International Airport (MDW) to Tampa (TPA)plane plane MDW - TPA
    2. Take a shuttle bus from Tampa International Airport - Red Terminal to Lake Sumter Depotshuttle bus
    7h 25m
    $152–475

  7. Fly Chicago O'Hare International Airport to Tampa, shuttle

    1. Fly from Chicago O'Hare International Airport (ORD) to Tampa (TPA)plane plane ORD - TPA
    2. Take a shuttle bus from Tampa International Airport - Red Terminal to Lake Sumter Depotshuttle bus
    7h 47m
    $162–435

  8. Fly Chicago Midway International Airport to Jacksonville, bus

    1. Fly from Chicago Midway International Airport (MDW) to Jacksonville (JAX)plane plane MDW - JAX
    2. Take the bus from Jacksonville to The Villages-Lady Lake Amtrak Bus Stopbus bus
    10h 44m

  9. Fly Chicago O'Hare International Airport to Jacksonville, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Jacksonville (JAX)plane plane ORD - JAX
    2. Take the bus from Jacksonville to The Villages-Lady Lake Amtrak Bus Stopbus bus
    11h 5m

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

Calendar66Weekly Planes
Duration3h 5mAverage Duration
Ticket$134Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to The Villages.ExpandLaunch map view
  • Distance: 1,075.9 mi
  • Duration: 6h 57m

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

You can take a bus from Chicago Bus Station to The Villages-Lady Lake Amtrak Bus Stop via Atlanta Bus Station, Jacksonville, JRTC Bay H, Amtrak Station, and Jacksonville in around 28h 56m.

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