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

Find Transport to Chicago

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There are 11 ways to get from DeLand to Chicago by plane, train, car, bus, train (Amtrak), or shuttle

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 Orlando Sanford to South Bend, train

    best
    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 44m
    $147–683

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

    cheapest
    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
    $79–414

  3. Drive, bus

    1. Drive from DeLand to Ocala, FLcar car
    2. Take the bus from Ocala, FL to University of Florida - 1956 Gale Lemerand Drbus bus
    3. Take the bus from Gainesville to Atlanta Bus Stationbus bus
    4. Take the bus from Atlanta Bus Station to Chicago Bus Stationbus bus
    28h 12m
    $169–288

  4. Train (Amtrak)

    1. Take the train from Deland to Chicago Union Stationtrain train Floridian
    39h 7m
    $452–1,202

  5. Drive  1,087.4 mi

    1. Drive from DeLand to Chicagocar car 1,087.4 mi
    19h 39m
    $199–287

  6. Fly Daytona Beach International Airport to Chicago Midway International Airport

    1. Fly from Daytona Beach International Airport (DAB) to Chicago Midway International Airport (MDW)plane plane DAB - MDW
    8h 4m
    $91–439

  7. 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 24m
    $199–504

  8. Fly Orlando Sanford to Indianapolis, shuttle, train

    1. Fly from Orlando Sanford (SFB) to Indianapolis (IND)plane plane SFB - IND
    2. Take a shuttle bus from Indianapolis Airport to Holiday Inn City Centreshuttle bus
    3. Take the train from Lafayette Amtrak Station to Chicago Union Stationtrain train
    9h 11m
    $167–736

  9. 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 53m
    $111–483

  10. 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
    $145–504

  11. 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 43m
    $442–1,183

DeLand to Chicago by bus and train (Amtrak)

Calendar7Weekly Services
Duration39h 7mAverage Duration
Ticket$452Cheapest Price
See schedules

Comparing Your Travel Options

Map of how to get from DeLand to Chicago.ExpandLaunch map view
  • Distance: 1,048.2 mi
  • Duration: 5h 44m

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

Amtrak operates a train from Deland to Chicago Union Station once daily. Tickets cost $450–1,200 and the journey takes 37h 56m. Alternatively, Delta, American Airlines, and Southwest Airlines fly from Daytona Beach International Airport (DAB) to Chicago Midway International Airport (MDW) 3 times a day.

Airlines
Train operators
Bus operators

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