Rome2Rio

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

Find Transport to Chicago

See all options

There are 11 ways to get from DeLand to Chicago by train, plane, 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. 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 14m
    $94–424

  2. Drive, bus

    1. Drive from DeLand to Ocalacar car
    2. Take the bus from Ocala to Gainesville - Commuter Lot Parking Garage @ Gale Lemerandbus 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
    27h 47m
    $159–324

  3. Train (Amtrak)

    1. Take the train from Deland to Chicago Union Stationtrain train Floridian
    39h 7m
    $502–1,102

  4. Drive 1,091.9 mi

    1. Drive from DeLand to Chicagocar car 1,091.9 mi
    19h 31m
    $200–288

  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
    6h 2m
    $156–681

  6. 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 46m
    $149–484

  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
    $156–683

  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 21m
    $145–589

  9. 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 14m
    $182–776

  10. 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 20m
    $126–513

  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 42m
    $194–828

DeLand to Chicago by bus and train (Amtrak)

Calendar7Weekly Services
Duration39h 7mAverage Duration
Ticket$502Cheapest Price
See schedules

Questions & Answers

Map of how to get from DeLand to Chicago.ExpandLaunch map view
  • Distance: 1,066.1 mi
  • Duration: 7h 14m

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 $500–1,100 and the journey takes 37h 56m.

Airlines
Train operators
Bus operators

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.

Related travel guides

Need to know: Greyhound

Read the travel guideNeed to know: Greyhound