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How to get fromHaines City to Chicagoby bus, train, plane, bus (Greyhound, Flixbus), train (Amtrak), or car

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There are 10 ways to get from Haines City to Chicago by bus, train, plane, 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. Line 416 bus, line 26 bus, train to Orlando, fly to Chicago Midway International Airport

    best
    1. Take the bus from Baker Ave. & 18th St. N. to Walmart Supercenter at Poincianabus bus
    2. Take the bus from Walmart Dr & Towne Center Dr to Pleasant St & Neptune Rdbus bus
    3. Take the train from Kissimmee to Sand Lake Roadtrain train
    4. Fly from Orlando (MCO) to Chicago Midway International Airport (MDW)plane plane MCO - MDW
    7h 35m
    $210–504

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

    cheapest
    1. Take the bus from Baker Ave. & 18th St. N. to Walmart Supercenter at Poincianabus bus
    2. Take the bus from Walmart Dr & Towne Center Dr to Pleasant St & Neptune Rdbus bus
    3. Take the train from Kissimmee to Sand Lake Roadtrain train
    4. Fly from Orlando (MCO) to Chicago O'Hare International Airport (ORD)plane plane MCO - ORD
    7h 58m
    $80–614

  3. Bus

    1. Take the bus from Winter Haven Transportation Center to Orlando Bus Stationbus bus
    2. Take the bus from Orlando Bus Station to Atlanta Bus Stationbus bus
    3. Take the bus from Atlanta Bus Station to Chicago Bus Stationbus bus
    26h 2m
    $204–406

  4. Train (Amtrak)

    1. Take the train from Kissimmee Amtrak Station to Chicago Union Stationtrain train Floridian
    41h 3m
    $635–1,301

  5. Drive 1,118.7 mi

    1. Drive from Haines City to Chicagocar car 1,118.7 mi
    20h 2m
    $205–295

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

    1. Take the bus from Winter Haven Transportation Center to Tampa Bus Stationbus bus
    2. Fly from Tampa (TPA) to Chicago Midway International Airport (MDW)plane plane TPA - MDW
    8h 15m
    $124–494

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

    1. Take the bus from Winter Haven Transportation Center to Tampa Bus Stationbus bus
    2. Fly from Tampa (TPA) to Chicago O'Hare International Airport (ORD)plane plane TPA - ORD
    8h 47m
    $188–594

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

    1. Drive from Haines City to Orlando-Sanford-Airport-SFBcar car
    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 48m
    $164–730

  9. Fly Orlando to General Mitchell International Airport, train

    1. Fly from Orlando (MCO) to General Mitchell International Airport (MKE)plane plane MCO - MKE
    2. Take the train from Milwaukee to Chicago Union Stationtrain train
    9h 57m
    $196–640

  10. Bus, bus to Sarasota–Bradenton International Airport, fly to Chicago Midway International Airport

    1. Take the bus from Winter Haven Transportation Center to Tampa Bus Stationbus bus
    2. Take the bus from Tampa Bus Station to Sarasota Cattlemen Transfer Centerbus bus
    3. Fly from Sarasota–Bradenton International Airport (SRQ) to Chicago Midway International Airport (MDW)plane plane SRQ - MDW
    10h 45m
    $156–660

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 Haines City to Chicago.ExpandLaunch map view
  • Distance: 1,056.9 mi
  • Duration: 7h 35m

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

You can take a bus from E. Hinson Ave. & N. 5th St. to Chicago Bus Station via Winter Haven Transportation Center, Orlando Bus Station, and Atlanta Bus Station in around 26h 2m. Alternatively, Amtrak operates a train from Kissimmee Amtrak Station to Chicago Union Station once daily. Tickets cost $550–1,200 and the journey takes 39h 35m.

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