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

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There are 9 ways to get from Florida to Chicago by plane, bus (Flixbus, Greyhound), 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. Fly Jacksonville to Chicago Midway International Airport

    best
    1. Fly from Jacksonville (JAX) to Chicago Midway International Airport (MDW)planeJAX - MDW
    5h 1m
    $114–608

  2. Fly Orlando to Chicago Midway International Airport

    cheapest
    1. Fly from Orlando (MCO) to Chicago Midway International Airport (MDW)planeMCO - MDW
    5h 5m
    $64–337

  3. Bus

    1. Take the bus from Jacksonville to Atlanta Bus StationbusFlixBus 2434 / ...
    2. Take the bus from Atlanta Bus Station to Chicago Bus StationbusGreyhound US0100
    24h 53m
    $142–413

  4. Train (Amtrak)

    1. Take the train from Jacksonville to Chicago Union StationtrainFloridian
    36h 40m
    $232–703

  5. Drive 981.9 mi

    1. Drive from Jacksonville to Chicagocar981.9 mi
    18h 15m
    $180–259

  6. Fly Jacksonville to Chicago O'Hare International Airport

    1. Fly from Jacksonville (JAX) to Chicago O'Hare International Airport (ORD)planeJAX - ORD
    5h 28m
    $89–438

  7. Fly Tampa to Chicago Midway International Airport

    1. Fly from Tampa (TPA) to Chicago Midway International Airport (MDW)planeTPA - MDW
    5h 7m
    $84–417

  8. Fly Tampa to Chicago O'Hare International Airport

    1. Fly from Tampa (TPA) to Chicago O'Hare International Airport (ORD)planeTPA - ORD
    5h 28m
    $99–317

  9. Fly Ft. Myers to Chicago Midway International Airport

    1. Fly from Ft. Myers (RSW) to Chicago Midway International Airport (MDW)planeRSW - MDW
    6h 14m
    $126–610

Florida to Chicago by bus

Calendar26Weekly Buses
Duration24h 53mAverage Duration
Ticket$142Cheapest Price
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Questions & Answers

What companies run services between Florida, USA and Chicago, IL, USA?

Southwest Airlines, Delta, and Frontier Airlines fly from Jacksonville (JAX) to Chicago Midway International Airport (MDW) 4 times a day. Alternatively, you can take a bus from Newnan St + Ashley St to Chicago Bus Station via JRTC Bay J, Jacksonville, and Atlanta Bus Station in around 24h 53m.

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Need to know: Greyhound

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