Rome2Rio

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

Find Transport to Chicago

See all options

There are 10 ways to get from DeLand to Chicago by plane, train, 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 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
    6h 9m
    $136–581

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

    cheapest
    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
    $89–424

  3. 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
    $148–320

  4. Train (Amtrak)

    1. Take the train from Deland to Chicago Union Stationtrain train Floridian
    39h 7m
    $192–552

  5. Drive 1,092 mi

    1. Drive from DeLand to Chicagocar car 1,092 mi
    19h 30m
    $200–288

  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 44m
    $94–364

  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
    $148–763

  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
    $112–514

  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
    $113–503

  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
    $161–369

DeLand to Chicago by bus and train (Amtrak)

Calendar7Weekly Services
Duration39h 7mAverage Duration
Ticket$192Cheapest Price
See schedules

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 $190–550 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

Where to next?

Trips from DeLand

Trips to Chicago

Popular routes