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How to get fromChicago to Oskaloosaby train, bus, car, plane, or bus (Flixbus, Greyhound)

Find Transport to Oskaloosa

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There are 6 ways to get from Chicago to Oskaloosa by train, bus, car, plane, or bus (Flixbus, Greyhound)

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, bus

    best
    1. Take the train from Chicago Union Station to Galesburg Amtrak Stationtrain train Southwest Chief / ...
    2. Take the bus from Galesburg to Oskaloosabus bus Greyhound US0157S
    7h 11m
    $116–177

  2. Drive  294.8 mi

    cheapest
    1. Drive from Chicago to Oskaloosacar car 294.8 mi
    5h 27m
    $53–76

  3. Fly Chicago O'Hare International Airport to Burlington Municipal Airport, drive

    1. Fly from Chicago O'Hare International Airport (ORD) to Burlington Municipal Airport (BRL)plane plane ORD - BRL
    2. Drive from Burlington Municipal Airport (BRL) to Oskaloosacar car
    5h 11m
    $96–312

  4. Bus

    1. Take the bus from Downtown Chicago to Illinois Terminalbus bus Chicago Area to Champaign SOUTH
    2. Take the bus from Champaign Intermodal Trans Ctr to Oskaloosabus bus Greyhound US0157S
    10h 10m
    $72–112

  5. Fly Chicago O'Hare International Airport to Des Moines, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Des Moines (DSM)plane plane ORD - DSM
    2. Take the bus from Des Moines to Oskaloosabus bus
    6h 37m
    $110–493

  6. Fly Chicago Midway International Airport to Des Moines, bus

    1. Fly from Chicago Midway International Airport (MDW) to Des Moines (DSM)plane plane MDW - DSM
    2. Take the bus from Des Moines to Oskaloosabus bus
    6h 23m
    $136–663

Chicago to Oskaloosa by train and bus

Calendar7Weekly Services
Duration7h 11mAverage Duration
Ticket$116Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Oskaloosa.ExpandLaunch map view
  • Distance: 307.6 mi
  • Duration: 7h 11m

What companies run services between Chicago, IL, USA and Oskaloosa, IA, USA?

You can take a bus from Downtown Chicago to Oskaloosa via Illinois Terminal and Champaign Intermodal Trans Ctr in around 10h 10m.

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