View Current Travel Advisories

Trailways Bus Tickets
from Chicago, IL to Oskaloosa, IA

(*) indicates a required field

Travel made simple with Trailways

Unbeatable Prices

One of the best inventories of bus tickets in one place - with exclusive fares you won't find elsewhere.

Proven Reliability

On-time travel services - trust our reputation for reliable bus transportation.

Comfort and Convenience

Numerous upgraded buses with large leather recliners, free wi-fi, and power outlets for each seat.
Overview

About buses from Chicago, IL to Oskaloosa, IA

Buses from Chicago, IL to Oskaloosa, IA travel the 254mi (408.77km) journey, taking approximately 20h, 50m. Usually, there is 1 bus operating per day. While the average ticket price for this journey is around $116.86, you can find the cheapest bus tickets for as low as $116.86.

  • Distance
    254mi (408.77km)
  • Average trip duration
  • Average bus ticket price
    $116.86
  • Trips per day
    1
  • Top Carriers
    FlixBus

Bus Station Information for Oskaloosa, IA

Oskaloosa

Flag Stop, use arrow keys or tab to explore more about this bus station

Oskaloosa, IA 52577

Advance Notice Required
Flag Stop
Address
501 High Avenue West 
Oskaloosa, IA 52577
Phone Number
(800) 858-8555
More Detailsabout Oskaloosa Flag Stop

City InformationforChicago, IL

There’s so much to see in the Windy City, you’ll be booking your next bus to Chicago before your trip is over. No matter the season, there’s plenty to do, from lounging on lakeside beaches in the summer to ice skating in Millennium Park.

Chicago’s famous for its dogs and its deep dish, if you’re looking for eats. Museums dot the map, including The Art Institute of Chicago, Field Museum, and Griffin Museum of Science and Industry. Catch a game if your sport’s in season – Bulls or Bears, Cubs or White Sox.

If you ask a local – which we always do – an Architecture Tour is on the don’t miss list. And if you’re on a budget, just go for a stroll on the Riverwalk, Navy Pier, or by “the bean” - Millennium Park’s famed Cloud Gate sculpture.

Whatever mood strikes you, Chi-town's got something to keep you busy.

Scenic photo of Chicago, ILScenic photo of Chicago, ILScenic photo of Chicago, IL
Scenic photo of Chicago, IL
Scenic photo of Chicago, IL
Scenic photo of Chicago, IL

City InformationforOskaloosa, IA

Hop on a bus to Oskaloosa, IA, and uncover the heartwarming charm this delightful town offers. Known for its welcoming spirit and quaint streets, Oskaloosa serves up a perfect escape for those seeking a unique blend of history and local flavor. Begin your journey with a visit to the historic downtown square, lined with shops and cafes that embody the town's vibrant community feel.

Make a stop at the George Daily Community Auditorium, where you might catch an engaging live performance, a local favorite. Art enthusiasts should check out the serene Oskaloosa Art Center, offering an oasis of creativity. If you prefer the outdoors, the peaceful beauty of Edmundson Park awaits, promising a scenic picnic or leisurely stroll. For something active, bring your bike and tackle the Mahaska County Recreation Trail.

Oskaloosa’s culinary scene will tempt your taste buds with down-home diners serving up hearty meals. As you plan your visit, remember, the adventure begins with a bus to Oskaloosa, where friendliness and discovery await around every corner.

Frequently Asked Questions about the Bus Ride

Reach Oskaloosa easily by bus from Chicago. If you want a fast and cheap way to get to Oskaloosa, or need an alternative to rail or airfare, Trailways helps you get there. Find the best bus tickets for you from Chicago to Oskaloosa.

Other Popular Routes for Chicago, IA and Oskaloosa, IA

Discover our Most Popular Routes Nationwide