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How to Travel from

Milwaukee to Winterset

by Plane, Train, Route or Car

Milwaukee
→
+0 →
Winterset
Transport search to Winterset
Simply select points
A and B, and we will create
a convenient route for you 👍
United States of America Milwaukee Winterset
Milwaukee
→
+0 →
Winterset
Building a composite car route
Simply select points
A and B, and we will create
a convenient route for you 👍
To build a composite route, click the "Add point" button.
You can also move and delete intermediate points.
Cheapest
Best Offer!
Car
20 h 56 min
1982 km.
from $109
Composite Route Car Only
Schedule

Milwaukee, United States of America → Winterset, United States of America

All
05 Apr 2026
April 2026
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All days
06 Apr, Mon
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Eight ways to Travel from Milwaukee to Winterset

Composite routes from Milwaukee to Winterset

Cheapest
20 h 56 min
Car
1982 km.
from $109
Other
10 h 32 min
Train, Bus, Taxi
537 km.
from $308.93
4 h 55 min
Bus, Plane
536 km.
from $253.12
6 h 20 min
Bus, Plane
536 km.
from $349.86
10 h 53 min
Bus, Taxi
537 km.
from $304.14
11 h 33 min
536 km.
from $236.28
12 h 5 min
536 km.
from $262.28

Transport providers

Airlines

American Airlines

Website:
aa.com/
Plane from General Mitchell International Airport to Des
Ave. Duration:
3h 55m
Frequency:
Every day
Estimated price:
$153.27–$638.63
Plane from Chicago O'Hare International Airport to Des
Ave. Duration:
1h 27m
Frequency:
Every day
Estimated price:
$108.57–$383.18

Delta

Website:
delta.com/
Plane from General Mitchell International Airport to Des
Ave. Duration:
4h 9m
Frequency:
Every day
Estimated price:
$140.50–$395.95

United Airlines

Website:
united.com/
Plane from General Mitchell International Airport to Des
Ave. Duration:
3h 56m
Frequency:
Every day
Estimated price:
$191.59–$638.63
Plane from Chicago O'Hare International Airport to Des
Ave. Duration:
1h 33m
Frequency:
Every day
Estimated price:
$140.50–$306.54
Plane from Chicago O'Hare International Airport to Fort
Ave. Duration:
1h 31m
Frequency:
Every day
Estimated price:
$166.04–$574.77

Southwest Airlines

Website:
southwest.com/
Plane from General Mitchell International Airport to Des
Ave. Duration:
3h 22m
Frequency:
Monday, Thursday, and Friday
Estimated price:
$153.27–$485.36

Train operators

Amtrak

Phone:
+1 800-872-7245
Website:
amtrak.com/home.html
Train from Milwaukee to Chicago
Ave. Duration:
1h 29m
Frequency:
Every 4 hours
Estimated price:
$12.77–$89.41
Train from Chicago Union Station to Galesburg
Ave. Duration:
2h 36m
Frequency:
4 times a day
Estimated price:
$22.99–$108.57

Bus operators

Greyhound USA

Phone:
+1 214-849-8100
Email:
Website:
greyhound.com/
Bus from Milwaukee Intermodal Station to Chicago
Ave. Duration:
2h 15m
Frequency:
Twice daily
Estimated price:
$7.02–$89.41

Flixbus USA

Phone:
+1 (855) 626-8585
Website:
flixbus.com
Bus from Milwaukee Intermodal Station to Chicago
Ave. Duration:
2h
Frequency:
3 times a day
Estimated price:
$11.50–$52.37

Burlington Trailways

Phone:
+1 (319) 735-2864
Email:
Website:
burlingtontrailways.com
Bus from Chicago to Des
Ave. Duration:
7h 10m
Frequency:
Once daily
Estimated price:
$76.64–$166.33
Bus from Galesburg to Burlington
Ave. Duration:
1h 10m
Frequency:
Once daily
Estimated price:
$29.38–$54.92
Bus from Burlington to Des
Ave. Duration:
3h 5m
Frequency:
Once daily
Estimated price:
$47.26–$95.79

Wisconsin Coach Lines Airport Express

Phone:
(866) 912 6224
Email:
Website:
coachusa.com/wisconsin-coach?gad_source=1&gclid=CjwKCAiAt4C-BhBcEiwA8Kp0Cc3RRg_kOdc3CzsoiFSe4BX-r10-kIOeuDNMfsAKsG5uubvoAmxcrRoC5LwQAvD_BwE
Bus from Milwaukee Intermodal Station to O'Hare
Ave. Duration:
1h 50m
Frequency:
Hourly
Estimated price:
$39.60–$43.43

Questions and Answers

What is the cheapest way to get from Milwaukee to Winterset?

The cheapest way to get from Milwaukee to Winterset is to drive which costs $70.65 - $108.70 and takes 6h 51m.

What is the fastest way to get from Milwaukee to Winterset?

The fastest way to get from Milwaukee to Winterset is to bus and fly which takes 4h 55m and costs $195.65 - $391.30 .

How far is it from Milwaukee to Winterset?

The distance between Milwaukee and Winterset is 562 km. The road distance is 658 km.

How do I travel from Milwaukee to Winterset without a car?

The best way to get from Milwaukee to Winterset without a car is to train and bus and taxi which takes 10h 32m and costs $152.17 - $315.22 .

How long does it take to get from Milwaukee to Winterset?

It takes approximately 5h 20m to get from Milwaukee to Winterset, including transfers.

Can I drive from Milwaukee to Winterset?

Yes, the driving distance between Milwaukee to Winterset is 658 km. It takes approximately 6h 51m to drive from Milwaukee to Winterset.

Where can I stay near Winterset?

There are four+ hotels available in Winterset. Prices start at $98.25 per night.
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