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

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There are 9 ways to get from DeLand to Chicago by plane, train, bus, 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 Daytona Beach International Airport to Chicago Midway International Airport

    best
    1. Fly from Daytona Beach International Airport (DAB) to Chicago Midway International Airport (MDW)plane plane DAB - MDW
    7h 55m
    $101–499

  2. Train, bus

    1. Take the train from Deland to Jacksonvilletrain train
    2. Take the bus from Jacksonville to Atlanta Bus Stationbus bus
    3. Take the bus from Atlanta Bus Station to Chicago Bus Stationbus bus
    28h 11m
    $245–423

  3. Train (Amtrak)

    1. Take the train from Deland to Chicago Union Stationtrain train Floridian
    39h 7m
    $902–1,502

  4. Drive  1,087.4 mi

    1. Drive from DeLand to Chicagocar car 1,087.4 mi
    19h 39m
    $180–260

  5. 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
    5h 47m
    $112–473

  6. Train to Orlando, fly to Chicago Midway International Airport

    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 29m
    $129–414

  7. 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
    $104–484

  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 22m
    $175–424

  9. 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 52m
    $464–1,198

DeLand to Chicago by bus, train, and taxi

Calendar14Weekly Services
Duration28h 11mAverage Duration
Ticket$245Cheapest Price
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Comparing Your Travel Options

Map of how to get from DeLand to Chicago.ExpandLaunch map view
  • Distance: 981.6 mi
  • Duration: 7h 55m

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

Delta, American Airlines, and Southwest Airlines fly from Daytona Beach International Airport (DAB) to Chicago Midway International Airport (MDW) 4 times a day. Alternatively, Amtrak operates a train from Deland to Chicago Union Station once daily. Tickets cost $900–1,500 and the journey takes 37h 56m.

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Want to know more about travelling around United States

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

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