There are 5 ways to get from Madison to Oskaloosa by bus, train, 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.
Bus, train
best- Take the bus from 250 N. Lake St - Madison UW Campus to W Jackson Blvd, after S Clinton Stbus
- Take the train from Chicago Union Station to Galesburg Amtrak Stationtrain
- Take the bus from Galesburg to Oskaloosabus
12h 11m$89–206Drive 247.8 mi
cheapest- Drive from Madison to Oskaloosacar 247.8 mi
5h$46–66Fly, bus
- Fly from Dane County Regional Airport-Truax Field (MSN) to Des Moines (DSM)plane MSN - DSM
- Take the bus from Des Moines to Oskaloosabus
8h 26m$123–569Bus, train via Milwaukee
- Take the bus from Madison, WI-Lake St. to Milwaukee, WI - Amtrakbus
- Take the train from Milwaukee to Chicago Union Stationtrain
- Take the train from Chicago Union Station to Galesburg Amtrak Stationtrain
- Take the bus from Galesburg to Oskaloosabus
12h 15m$104–245Bus
- Take the bus from Madison to Saint Paul Union Depotbus
- Take the bus from Saint Paul Union Depot to Des Moinesbus
- Take the bus from Des Moines to Oskaloosabus
12h 35m$111–173
Madison to Oskaloosa by bus and train
Comparing Your Travel Options
The cheapest way to get from Madison to Oskaloosa is to drive which costs $45 - $70 and takes 5h.
The fastest way to get from Madison to Oskaloosa is to drive which takes 5h and costs $45 - $70.
No, there is no direct bus from Madison to Oskaloosa. However, there are services departing from Madison and arriving at Oskaloosa via Saint Paul Union Depot and Des Moines. The journey, including transfers, takes approximately 12h 35m.
The distance between Madison and Oskaloosa is 467 miles. The road distance is 249.3 miles.
The best way to get from Madison to Oskaloosa without a car is to bus and train which takes 12h 11m and costs $85 - $210.
It takes approximately 12h 11m to get from Madison to Oskaloosa, including transfers.
Madison to Oskaloosa bus services, operated by Flixbus USA, depart from Madison station.
Madison to Oskaloosa bus services, operated by Flixbus USA, arrive at Saint Paul Union Depot station.
Yes, the driving distance between Madison to Oskaloosa is 249 miles. It takes approximately 5h to drive from Madison to Oskaloosa.
Book your Madison to Oskaloosa bus tickets online with Omio and FlixBus.
What companies run services between Madison, WI, USA and Oskaloosa, IA, USA?
You can take a bus from Madison to Oskaloosa via Saint Paul Union Depot and Des Moines in around 12h 35m.
- Website
- united.com
Flights from Dane County Regional Airport-Truax Field to Des Moines via Chicago O'Hare
- Ave. Duration
- 4h 32m
- When
- Every day
- Estimated price
- $55–340
Flights from Dane County Regional Airport-Truax Field to Des Moines via Denver
- Ave. Duration
- 6h 22m
- When
- Every day
- Estimated price
- $110–550
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Chicago Union Station to Galesburg Amtrak Station
- Ave. Duration
- 2h 36m
- Frequency
- 4 times a day
- Estimated price
- $40–110
- Website
- Amtrak
Train from Milwaukee to Chicago Union Station
- Ave. Duration
- 1h 29m
- Frequency
- Every 4 hours
- Estimated price
- $21–55
- Website
- Amtrak
Train from Chicago Union Station to Galesburg Amtrak Station
- Ave. Duration
- 2h 36m
- Frequency
- 4 times a day
- Estimated price
- $40–110
- Website
- Amtrak
- Phone
- +1 (866) 912 - 6224
- [email protected]
- Website
- Rockland Coaches
Bus from 250 N. Lake St - Madison UW Campus to W Jackson Blvd, after S Clinton St
- Ave. Duration
- 4h
- Frequency
- Hourly
- Estimated price
- $26–60
- Schedules at
- Rockland Coaches
- Adult
- $26–60
Want to know more about travelling around United States
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Booking & Getting There
There are five+ hotels available in Oskaloosa.






