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

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There are 10 ways to get from DeLand to Chicago by train, 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. Train to Orlando, fly to Chicago Midway International Airport

    best
    1. Take the train from DeLand to Sand Lake Roadtrain train
    2. Fly from Orlando (MCO) to Chicago Midway International Airport (MDW)plane plane MCO - MDW
    7h 24m
    $84–424

  2. Bus

    1. Take the bus from Orlando Bus Station to Atlanta Bus Stationbus bus FlixBus N2401 / ...
    2. Take the bus from Atlanta Bus Station to Chicago Bus Stationbus bus FlixBus 2512 / ...
    26h 2m
    $143–370

  3. Train (Amtrak)

    1. Take the train from Deland to Chicago Union Stationtrain train Floridian
    39h 7m
    $282–702

  4. Drive 1,092 mi

    1. Drive from DeLand to Chicagocar car 1,092 mi
    19h 29m
    $200–288

  5. Train to Orlando, fly to Chicago O'Hare International Airport

    1. Take the train from DeLand to Sand Lake Roadtrain train
    2. Fly from Orlando (MCO) to Chicago O'Hare International Airport (ORD)plane plane MCO - ORD
    7h 44m
    $89–334

  6. Fly Orlando Sanford to South Bend, train

    1. Fly from Orlando Sanford (SFB) to South Bend (SBN)plane plane SFB - SBN
    2. Take the train from South Bend Airport to Van Buren St.train train
    6h 17m
    $136–631

  7. Train to Jacksonville, fly to Chicago Midway International Airport

    1. Take the train from Deland to Jacksonvilletrain train
    2. Fly from Jacksonville (JAX) to Chicago Midway International Airport (MDW)plane plane JAX - MDW
    9h 52m
    $138–758

  8. Train to Tampa, fly to Chicago Midway International Airport

    1. Take the train from Deland to Tampatrain train
    2. Fly from Tampa (TPA) to Chicago Midway International Airport (MDW)plane plane TPA - MDW
    10h 27m
    $107–514

  9. Train to Jacksonville, fly to Chicago O'Hare International Airport

    1. Take the train from Deland to Jacksonvilletrain train
    2. Fly from Jacksonville (JAX) to Chicago O'Hare International Airport (ORD)plane plane JAX - ORD
    10h 19m
    $108–538

  10. Train to Orlando, fly to General Mitchell International Airport, train

    1. Take the train from DeLand to Sand Lake Roadtrain train
    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
    9h 49m
    $161–679

DeLand to Chicago by bus and train (Amtrak)

Calendar7Weekly Services
Duration39h 7mAverage Duration
Ticket$282Cheapest Price
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Questions & Answers

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

You can take a bus from Deland Intermodal Transit Fac to Chicago Bus Station via Debary Sunrail Station, DeBary, Winter Park, Orlando Bus Station, and Atlanta Bus Station in around 26h 2m. Alternatively, Amtrak operates a train from Deland to Chicago Union Station once daily. Tickets cost $280–700 and the journey takes 37h 56m.

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