Rome2Rio

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

Find Transport to Chicago

See all options

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

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Bus, train

    best
    1. Take the bus from Oskaloosa to Galesburgbus bus Greyhound US0157S
    2. Take the train from Galesburg Amtrak Station to Chicago Union Stationtrain train Carl Sandburg / ...
    7h 5m
    $111–179

  2. Drive  295.5 mi

    cheapest
    1. Drive from Oskaloosa to Chicagocar car 295.5 mi
    5h 28m
    $54–78

  3. Bus to Des Moines, fly to Chicago O'Hare International Airport

    1. Take the bus from Oskaloosa to Des Moinesbus bus
    2. Fly from Des Moines (DSM) to Chicago O'Hare International Airport (ORD)plane plane DSM - ORD
    5h 47m
    $105–482

  4. Bus

    1. Take the bus from Oskaloosa to Champaign Intermodal Trans Ctrbus bus Greyhound US0157S
    2. Take the bus from Champaign Intermodal Trans Ctr to Chicago Bus Stationbus bus FlixBus N2521 / ...
    9h 20m
    $96–135

  5. Bus to Des Moines, fly to Chicago Midway International Airport

    1. Take the bus from Oskaloosa to Des Moinesbus bus
    2. Fly from Des Moines (DSM) to Chicago Midway International Airport (MDW)plane plane DSM - MDW
    5h 26m
    $120–562

  6. Bus, bus to Waterloo Municipal Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Oskaloosa to Des Moinesbus bus
    2. Take the bus from Des Moines to Waterloobus bus
    3. Fly from Waterloo Municipal Airport (ALO) to Chicago O'Hare International Airport (ORD)plane plane ALO - ORD
    8h 41m
    $83–318

Oskaloosa to Chicago by bus and train

Calendar7Weekly Services
Duration7h 5mAverage Duration
Ticket$111Cheapest Price
See schedules

Comparing Your Travel Options

Map of how to get from Oskaloosa to Chicago.ExpandLaunch map view
  • Distance: 307.2 mi
  • Duration: 7h 5m

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

You can take a bus from Oskaloosa to Chicago Bus Station via Champaign Intermodal Trans Ctr in around 9h 20m.

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

Booking & Getting There