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How to get fromLeesburg to Chicagoby shuttle, plane, taxi, bus, train, or car

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There are 10 ways to get from Leesburg to Chicago by shuttle, plane, taxi, bus, train, or car

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 Brownwood Hotel & Spa to MCO Airport - Terminal Ashuttle bus
    2. Fly from Orlando (MCO) to Chicago Midway International Airport (MDW)plane plane MCO - MDW
    5h 51m
    $265–578

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

    cheapest
    1. Take a shuttle bus from Brownwood Hotel & Spa to MCO Airport - Terminal Ashuttle bus
    2. Fly from Orlando (MCO) to Chicago O'Hare International Airport (ORD)plane plane MCO - ORD
    6h 14m
    $135–688

  3. Taxi, bus

    1. Take the taxi from Leesburg to Ocala, FLtaxi taxi
    2. Take the bus from Ocala, FL to University of Florida - 1956 Gale Lemerand Drbus bus
    3. Take the bus from Gainesville to Atlanta Bus Stationbus bus
    4. Take the bus from Atlanta Bus Station to Chicago Bus Stationbus bus
    26h 55m
    $262–430

  4. Taxi, train

    1. Take the taxi from Leesburg to Delandtaxi taxi
    2. Take the train from Deland to Chicago Union Stationtrain train Floridian
    38h 51m
    $597–1,215

  5. Drive 1,064.3 mi

    1. Drive from Leesburg to Chicagocar car 1,064.3 mi
    19h 11m
    $195–281

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

    1. Take a shuttle bus from Brownwood Hotel & Spa to Tampa International Airport - Red Terminalshuttle bus
    2. Fly from Tampa (TPA) to Chicago Midway International Airport (MDW)plane plane TPA - MDW
    6h 38m
    $205–508

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

    1. Take a shuttle bus from Brownwood Hotel & Spa to Tampa International Airport - Red Terminalshuttle bus
    2. Fly from Tampa (TPA) to Chicago O'Hare International Airport (ORD)plane plane TPA - ORD
    7h 9m
    $235–658

  8. Taxi to Orlando Sanford, fly to South Bend, train

    1. Take the taxi from Leesburg to Orlando-Sanford-Airport-SFBtaxi taxi
    2. Fly from Orlando Sanford (SFB) to South Bend (SBN)plane plane SFB - SBN
    3. Take the train from South Bend Airport to Van Buren St.train train
    6h 27m
    $244–784

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

    1. Take a shuttle bus from Brownwood Hotel & Spa 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 14m
    $382–1,257

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

    1. Take the bus from Wildwood Amtrak Station to Jacksonvillebus bus
    2. Fly from Jacksonville (JAX) to Chicago Midway International Airport (MDW)plane plane JAX - MDW
    10h 47m
    $172–575

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

Calendar50Weekly Planes
Duration3h 2mAverage Duration
Ticket$83Cheapest Price
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Questions & Answers

Map of how to get from Leesburg to Chicago.ExpandLaunch map view
  • Distance: 1,072.3 mi
  • Duration: 5h 51m

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

There is no direct connection from Leesburg to Chicago. However, you can take the taxi to Brownwood Hotel & Spa, take the shuttle to MCO Airport - Terminal A, walk to Orlando (MCO) airport, fly to Chicago Midway International Airport (MDW), walk to Midway, then take the subway to Harold Washington Library. Alternatively, you can take the taxi to Ocala, FL, take the bus to University of Florida - 1956 Gale Lemerand Dr, walk to Reitz Union, take the line 46 bus to Rosa Parks RTS Downtown Station, walk to Gainesville, take the bus to Atlanta Bus Station, then take the bus to Chicago Bus Station.

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