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How to get fromChicago to Haines Cityby subway, plane, train, bus, bus (Greyhound, Flixbus), train (Amtrak), or car

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There are 9 ways to get from Chicago to Haines City by subway, plane, train, bus, bus (Greyhound, Flixbus), train (Amtrak), 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. Subway to Chicago Midway International Airport, fly to Orlando, train, line 26 bus, line 416 bus

    best
    1. Take the subway from Adams/Wabash to Midwaysubway subway
    2. Fly from Chicago Midway International Airport (MDW) to Orlando (MCO)plane plane MDW - MCO
    3. Take the train from Sand Lake Road to Kissimmeetrain train
    4. Take the bus from Pleasant St & Neptune Rd to Walmart Dr & Towne Center Drbus bus
    5. Take the bus from Walmart Supercenter at Poinciana to Haines City Health Departmentbus bus
    8h 13m
    $210–505

  2. Fly Chicago O'Hare International Airport to Orlando, train, line 26 bus, line 416 bus

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Orlando (MCO)plane plane ORD - MCO
    2. Take the train from Sand Lake Road to Kissimmeetrain train
    3. Take the bus from Pleasant St & Neptune Rd to Walmart Dr & Towne Center Drbus bus
    4. Take the bus from Walmart Supercenter at Poinciana to Haines City Health Departmentbus bus
    8h 39m
    $80–615

  3. Bus

    1. Take the bus from Chicago Bus Station to Atlanta Bus Stationbus bus
    2. Take the bus from Atlanta Bus Station to Orlando Bus Stationbus bus
    3. Take the bus from Orlando Bus Station to Winter Haven Transportation Centerbus bus
    26h 35m
    $210–398

  4. Train (Amtrak)

    1. Take the train from Chicago Union Station to Kissimmee Amtrak Stationtrain train Floridian
    40h 14m
    $644–1,229

  5. Drive 1,117.4 mi

    1. Drive from Chicago to Haines Citycar car 1,117.4 mi
    20h 2m
    $204–295

  6. Fly Chicago Midway International Airport to Tampa, bus

    1. Fly from Chicago Midway International Airport (MDW) to Tampa (TPA)plane plane MDW - TPA
    2. Take the bus from Tampa Bus Station to Winter Haven Transportation Centerbus bus
    9h 8m
    $190–644

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

    1. Fly from Chicago O'Hare International Airport (ORD) to Tampa (TPA)plane plane ORD - TPA
    2. Take the bus from Tampa Bus Station to Winter Haven Transportation Centerbus bus
    9h 37m
    $190–594

  8. Train to General Mitchell International Airport, fly to Orlando

    1. Take the train from Chicago Union Station to Milwaukeetrain train
    2. Fly from General Mitchell International Airport (MKE) to Orlando (MCO)plane plane MKE - MCO
    9h 51m
    $208–685

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

    1. Fly from Chicago Midway International Airport (MDW) to Sarasota–Bradenton International Airport (SRQ)plane plane MDW - SRQ
    2. Take the bus from Sarasota Cattlemen Transfer Center to Tampa Bus Stationbus bus
    3. Take the bus from Tampa Bus Station to Winter Haven Transportation Centerbus bus
    11h 28m
    $208–861

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

Calendar45Weekly Planes
Duration2h 55mAverage Duration
Ticket$118Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Haines City.ExpandLaunch map view
  • Distance: 1,046.8 mi
  • Duration: 8h 13m

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

You can take a bus from Chicago Bus Station to Haines City Plaza via Atlanta Bus Station, Orlando Bus Station, and Winter Haven Terminal in around 26h 35m. Alternatively, Amtrak operates a train from Chicago Union Station to Kissimmee Amtrak Station once daily. Tickets cost $550–1,200 and the journey takes 38h 58m.

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