There are 7 ways to get from Chicago to Upson by plane, train, bus, car, or bus (Flixbus)
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Fly to Gogebic–Iron County Airport
best- Fly from Chicago O'Hare International Airport (ORD) to Gogebic–Iron County Airport (IWD)plane ORD - IWD
3h 32m$212–460Fly to Central Wisconsin Airport, drive
cheapest- Fly from Chicago O'Hare International Airport (ORD) to Central Wisconsin Airport (CWA)plane ORD - CWA
- Drive from Central Wisconsin Airport (CWA) to Upsoncar
6h 6m$64–305Train, bus
- Take the train from Chicago Union Station to Milwaukeetrain
- Take the bus from Milwaukee to Escanababus
- Take the bus from Escanaba to Ironwoodbus
12h 45m$128–239Train, bus via Saint Paul
- Take the train from Chicago Union Station to St. Paul-Minneapolistrain
- Take the bus from St. Paul to Duluthbus
- Take the bus from Duluth to Hurleybus
14h 26m$212–435Drive 402.6 mi
- Drive from Chicago to Upsoncar 402.6 mi
7h 39m$74–107Fly to Houghton County Memorial Airport, drive
- Fly from Chicago O'Hare International Airport (ORD) to Houghton County Memorial Airport (CMX)plane ORD - CMX
- Drive from Houghton County Memorial Airport (CMX) to Upsoncar
6h 2m$70–320Bus
- Take the bus from Chicago Bus Station to Green Bay Transit Centerbus
- Take the bus from Green Bay to Escanababus
- Take the bus from Escanaba to Ironwoodbus
13h 51m$124–201
Chicago O'Hare International Airport (ORD) to Gogebic–Iron County Airport (IWD) flights
Comparing Your Travel Options
The cheapest way to get from Chicago to Upson is to drive which costs $70 - $110 and takes 7h 39m.
The fastest way to get from Chicago to Upson is to fly which takes 3h 32m and costs $210 - $460.
No, there is no direct bus from Chicago station to Upson. However, there are services departing from Chicago Bus Station and arriving at Ironwood via Green Bay and Escanaba. The journey, including transfers, takes approximately 13h 51m.
The distance between Chicago and Upson is 373 miles. The road distance is 404.9 miles.
The best way to get from Chicago to Upson without a car is to train and bus which takes 12h 45m and costs $120 - $240.
It takes approximately 3h 32m to get from Chicago to Upson, including transfers.
Chicago to Upson bus services, operated by Flixbus USA, depart from Chicago Bus Station.
The best way to get from Chicago to Upson is to fly which takes 3h 32m and costs $210 - $460. Alternatively, you can bus, which costs $120 - $210 and takes 13h 51m.
Chicago to Upson bus services, operated by Flixbus USA, arrive at Green Bay Transit Center station.
Yes, the driving distance between Chicago to Upson is 405 miles. It takes approximately 7h 39m to drive from Chicago to Upson.
What companies run services between Chicago, IL, USA and Upson, WI, USA?
Key Lime flies from Chicago O'Hare International Airport (ORD) to Gogebic–Iron County Airport (IWD) 6 times a week. Alternatively, you can take a bus from Chicago Bus Station to Upson via Green Bay, Escanaba, and Ironwood in around 13h 51m.
- Website
- aa.com
Flights from Chicago O'Hare International Airport to Central Wisconsin Airport
- Ave. Duration
- 1h 20m
- When
- Every day
- Estimated price
- $35–260
- Website
- united.com
Flights from Chicago O'Hare International Airport to Houghton County Memorial Airport
- Ave. Duration
- 1h 38m
- When
- Every day
- Estimated price
- $45–280
- Website
- keylimeair.com
Flights from Chicago O'Hare International Airport to Gogebic–Iron County Airport
- Ave. Duration
- 1h 15m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $150–380
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Chicago Union Station to Milwaukee
- Ave. Duration
- 1h 29m
- Frequency
- Every 4 hours
- Estimated price
- $23–60
- Website
- Amtrak
Train from Chicago Union Station to St. Paul-Minneapolis
- Ave. Duration
- 7h 31m
- Frequency
- 3 times a day
- Estimated price
- $110–290
- Website
- Amtrak
- Phone
- +1 989-725-5105
- Website
- Indian Trails
Bus from Milwaukee to Escanaba
- Ave. Duration
- 5h 15m
- Frequency
- Once daily
- Estimated price
- $35–70
- Website
- Indian Trails
Bus from Escanaba to Ironwood
- Ave. Duration
- 3h 40m
- Frequency
- Once daily
- Estimated price
- $30–55
- Website
- Indian Trails
Bus from Duluth to Hurley
- Ave. Duration
- 2h 15m
- Frequency
- Once daily
- Estimated price
- $19–40
- Website
- Indian Trails
Bus from Green Bay to Escanaba
- Ave. Duration
- 2h 35m
- Frequency
- Once daily
- Estimated price
- $20–40
- Website
- Indian Trails
Bus from Escanaba to Ironwood
- Ave. Duration
- 3h 40m
- Frequency
- Once daily
- Estimated price
- $30–55
- Website
- Indian Trails
- Phone
- +1-858-800-8898
- Website
- jeffersonlines.com
Bus from St. Paul to Duluth
- Ave. Duration
- 2h 20m
- Frequency
- Twice daily
- Estimated price
- $40–60
- Book at
- Jefferson Lines
- Adult
- $40–60
- Phone
- +1 (855) 626-8585
- Website
- Flixbus USA
Bus from Chicago Bus Station to Green Bay Transit Center
- Ave. Duration
- 5h 15m
- Frequency
- 5 times a week
- Estimated price
- $30–55
- Schedules at
- Flixbus USA
Want to know more about travelling around United States
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Booking & Getting There
There are 52+ hotels available in Upson.









