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How to get fromChicago to Oskaloosaby train, bus, car, plane, or shuttle

Find Transport to Oskaloosa

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There are 6 ways to get from Chicago to Oskaloosa by train, bus, car, plane, 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, 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
    $76–151

  2. Drive 294.8 mi

    cheapest
    1. Drive from Chicago to Oskaloosacar car 294.8 mi
    5h 27m
    $54–78

  3. Fly 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 7m
    $76–163

  4. Bus

    1. Take the bus from Chicago to Des Moinesbus bus Btw 1205 / ...
    2. Take the bus from Des Moines to Oskaloosabus bus Btw 1402
    9h 10m

  5. Bus via Peoria

    1. Take the bus from Oakbrook Mall to Peoriabus bus Peoria line
    2. Take the bus from Peoria to Oskaloosabus bus Btw 1401
    13h 12m

  6. Fly to Des Moines, shuttle, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Des Moines (DSM)plane plane ORD - DSM
    2. Take a shuttle bus from Des Moines International Airport, IA to Ames, IA - Iowa State Universityshuttle bus
    3. Take the bus from Ames to Des Moinesbus bus
    4. Take the bus from Des Moines to Oskaloosabus bus
    8h 12m

Chicago to Oskaloosa by train and bus

Calendar14Weekly Services
Duration7h 11mAverage Duration
Ticket$76Cheapest Price
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Questions & Answers

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 Chicago to Oskaloosa via Des Moines in around 9h 10m.

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