There are 7 ways to get from Winterset to Chicago by taxi, plane, bus, car, or train
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Taxi to Des Moines, fly to Chicago O'Hare International Airport
best- Take the taxi from Winterset to Des-Moines-Airport-DSM
- Fly from Des Moines (DSM) to Chicago O'Hare International Airport (ORD)DSM - ORD
3h 4m$131–467Drive to Fort Dodge Municipal Airport, fly to Chicago O'Hare International Airport
cheapest- Drive from Winterset to Fort Dodge Municipal Airport (FOD)
- Fly from Fort Dodge Municipal Airport (FOD) to Chicago O'Hare International Airport (ORD)FOD - ORD
4h 21m$54–270Taxi, bus
- Take the taxi from Winterset to Des Moines
- Take the bus from Des Moines to ChicagoOmaha
6h 50m$145–245Drive 366.8 mi
- Drive from Winterset to Chicago366.8 mi
6h 10m$67–97Taxi to Des Moines, fly to Chicago Midway International Airport
- Take the taxi from Winterset to Des-Moines-Airport-DSM
- Fly from Des Moines (DSM) to Chicago Midway International Airport (MDW)DSM - MDW
2h 47m$151–637Taxi, bus via Des Moines (Greyhound)
- Take the taxi from Winterset to Des Moines
- Take the bus from Des Moines to Chicago Bus StationGreyhound US0123 / ...
7h 36m$135–246Taxi, bus, train
- Take the taxi from Winterset to Des Moines
- Take the bus from Des Moines to Burlington
- Take the bus from Burlington to Galesburg
- Take the train from Galesburg Amtrak Station to Chicago Union Station
9h 37m$169–308
Des Moines (DSM) to Chicago O'Hare International Airport (ORD) flights
Questions & Answers
The cheapest way to get from Winterset to Chicago is to drive which costs $65 - $100 and takes 6h 10m.
The fastest way to get from Winterset to Chicago is to taxi and fly which takes 2h 47m and costs $150 - $650.
The distance between Winterset and Chicago is 347 miles. The road distance is 368.9 miles.
The best way to get from Winterset to Chicago without a car is to taxi and bus which takes 6h 50m and costs $140 - $250.
It takes approximately 3h 4m to get from Winterset to Chicago, including transfers.
Yes, the driving distance between Winterset to Chicago is 369 miles. It takes approximately 6h 10m to drive from Winterset to Chicago.
There are 1169+ hotels available in Chicago.
What companies run services between Winterset, IA, USA and Chicago, IL, USA?
There is no direct connection from Winterset to Chicago. However, you can take the taxi to Des-Moines-Airport-DSM airport, fly to Chicago O'Hare International Airport (ORD), walk to O'Hare, then take the subway to Jackson-Blue. Alternatively, you can take the taxi to Des Moines then take the bus to Chicago.
Transport is disrupted due to the Russia-Ukraine war. Read more
- Website
- united.com
Flights from Des Moines to Chicago O'Hare International Airport
- Ave. Duration
- 1h 33m
- When
- Every day
- Estimated price
- $60–380
Flights from Fort Dodge Municipal Airport to Chicago O'Hare International Airport
- Ave. Duration
- 1h 34m
- When
- Every day
- Estimated price
- $35–240
- Website
- aa.com
Flights from Des Moines to Chicago O'Hare International Airport
- Ave. Duration
- 1h 48m
- When
- Every day
- Estimated price
- $60–380
- Website
- delta.com
Flights from Des Moines to Chicago O'Hare International Airport via Minneapolis
- Ave. Duration
- 3h 58m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $80–440
- Website
- southwest.com
Flights from Des Moines to Chicago Midway International Airport
- Ave. Duration
- 1h 20m
- When
- Monday, Thursday, and Friday
- Estimated price
- $80–550
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Galesburg Amtrak Station to Chicago Union Station
- Ave. Duration
- 2h 55m
- Frequency
- 3 times a day
- Estimated price
- $21–80
- Website
- https://www.amtrak.com/home.html
- Phone
- +1 (319) 753-2864
- info@burlingtontrailways.com
- Website
- burlingtontrailways.com
Bus from Des Moines to Chicago
- Ave. Duration
- 6h 10m
- Frequency
- Once daily
- Estimated price
- $65–143
- Website
- https://burlingtontrailways.com
- Saver Fares
- $65–100
- Flexible Fares
- $90–140
- Saver Fare
- $104
- Flex Fare
- $143
Bus from Des Moines to Burlington
- Ave. Duration
- 3h
- Frequency
- Once daily
- Estimated price
- $40–80
- Website
- https://burlingtontrailways.com
- Saver Fares
- $40–60
- Flexible Fares
- $50–80
Bus from Burlington to Galesburg
- Ave. Duration
- 1h
- Frequency
- Once daily
- Estimated price
- $25–50
- Website
- https://burlingtontrailways.com
- Saver Fares
- $25–40
- Flexible Fares
- $30–50
Rome2Rio's guide to Greyhound USA
Contact Details
- Phone
- +1 214-849-8100
- ifsr@greyhound.com
- Website
- greyhound.com
Bus from Des Moines to Chicago Bus Station
- Ave. Duration
- 6h 50m
- Frequency
- 3 times a day
- Estimated price
- $45–140
- Website
- https://www.greyhound.com/
- Ave. Duration
- 44 min
- Estimated price
- $65–110
Want to know more about travelling around United States
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