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

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There are 10 ways to get from Chicago to Leesburg by plane, shuttle, bus (Greyhound, Flixbus), 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 Tampa, shuttle

    best
    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 Brownwood Hotel & Spashuttle bus
    7h 9m
    $210–510

  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 A to Spanish Springsshuttle bus
    8h 29m
    $108–661

  3. Bus

    1. Take the bus from Chicago Bus Station to Nashville Bus Stationbus bus
    2. Take the bus from Nashville Bus Station to Tallahasseebus bus
    3. Take the bus from Tallahassee to Wildwoodbus bus
    25h 43m
    $235–394

  4. Train, taxi

    1. Take the train from Chicago Union Station to Delandtrain train Floridian
    2. Take the taxi from Deland to Leesburgtaxi taxi
    38h 8m
    $637–1,220

  5. Drive 1,062.9 mi

    1. Drive from Chicago to Leesburgcar car 1,062.9 mi
    19h 11m
    $194–281

  6. 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 Brownwood Hotel & Spashuttle bus
    7h 38m
    $240–660

  7. Fly Chicago Midway International Airport to Orlando, shuttle

    1. Fly from Chicago Midway International Airport (MDW) to Orlando (MCO)plane plane MDW - MCO
    2. Take a shuttle bus from MCO Airport - Terminal A to Spanish Springsshuttle bus
    8h 3m
    $238–551

  8. Train to South Bend, fly to Orlando Sanford, taxi

    1. Take the train from Van Buren St. to South Bend Airporttrain train
    2. Fly from South Bend (SBN) to Orlando Sanford (SFB)plane plane SBN - SFB
    3. Take the taxi from Orlando-Sanford-Airport-SFB to Leesburgtaxi taxi
    6h 30m
    $213–634

  9. 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 Wildwood Amtrak Stationbus bus
    11h 25m
    $190–721

  10. Fly Chicago Midway International Airport to Sarasota–Bradenton International Airport, bus, taxi

    1. Fly from Chicago Midway International Airport (MDW) to Sarasota–Bradenton International Airport (SRQ)plane plane MDW - SRQ
    2. Take the bus from Bradenton/Sarasota - Mobil Gas Station to Ocala, FLbus bus
    3. Take the taxi from Ocala, FL to Leesburgtaxi taxi
    9h 43m
    $280–984

Chicago Midway International Airport (MDW) to Tampa (TPA) flights

Calendar39Weekly Planes
Duration2h 59mAverage Duration
Ticket$124Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Leesburg.ExpandLaunch map view
  • Distance: 1,129.1 mi
  • Duration: 7h 9m

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

You can take a bus from Chicago Bus Station to Leesburg via Nashville Bus Station, C.K. Steele Plaza Gate 16, N Monroe Street and John Knox Road, Tallahassee, and Wildwood in around 25h 43m.

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