There are 8 ways to get from Chicago to Upson by plane, train, bus, car, bus (Greyhound, Flixbus), or bus (Greyhound)
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 35m$192–280Fly 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 8m$58–295Train, bus
- Take the train from Chicago Union Station to Milwaukeetrain
- Take the bus from Milwaukee to Escanababus
- Take the bus from Escanaba, MI to Ironwoodbus
12h 45m$128–229Train, bus via Saint Paul
- Take the train from Chicago Union Station to St. Paul-Minneapolistrain
- Take the bus from St. Paul to Duluthbus Moa
- Take the bus from Duluth Transportation Center East to Hurley, WIbus
14h 19m$209–388Drive 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 5m$66–320Bus
- Take the bus from Chicago Bus Station to Milwaukee Intermodal Stationbus
- Take the bus from Milwaukee to Escanababus
- Take the bus from Escanaba, MI to Ironwoodbus
12h 56m$117–207Bus via Manitowoc
- Take the bus from Chicago Bus Station to Manitowocbus
- Take the bus from Manitowoc, WI to Escanababus
- Take the bus from Escanaba, MI to Ironwoodbus
13h 51m$123–213
Chicago O'Hare International Airport (ORD) to Gogebic–Iron County Airport (IWD) flights
Questions & Answers
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 35m and costs $190 - $280.
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 - $230.
It takes approximately 3h 35m to get from Chicago to Upson, including transfers.
The best way to get from Chicago to Upson is to fly which takes 3h 35m and costs $190 - $280. Alternatively, you can bus, which costs $110 - $210 and takes 12h 56m.
Yes, the driving distance between Chicago to Upson is 405 miles. It takes approximately 7h 39m to drive from Chicago to Upson.
There are 53+ hotels available in 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 Milwaukee Intermodal Station, Milwaukee, Escanaba, MI, and Ironwood in around 12h 56m.
- Website
- aa.com
Flights from Chicago O'Hare International Airport to Central Wisconsin Airport
- Ave. Duration
- 1h 19m
- When
- Every day
- Estimated price
- $30–250
- Website
- united.com
Flights from Chicago O'Hare International Airport to Central Wisconsin Airport
- Ave. Duration
- 1h 17m
- When
- Every day
- Estimated price
- $30–250
Flights from Chicago O'Hare International Airport to Houghton County Memorial Airport
- Ave. Duration
- 1h 35m
- When
- Every day
- Estimated price
- $40–280
- 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
- $130–200
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Chicago Union Station to Milwaukee
- Ave. Duration
- 1h 29m
- Frequency
- Every 4 hours
- Estimated price
- $22–50
- Website
- https://www.amtrak.com/home.html
Train from Chicago Union Station to St. Paul-Minneapolis
- Ave. Duration
- 7h 24m
- Frequency
- 3 times a day
- Estimated price
- $110–240
- Website
- https://www.amtrak.com/home.html
- Phone
- +1 989-725-5105
- Website
- indiantrails.com
Bus from Milwaukee to Escanaba
- Ave. Duration
- 5h 15m
- Frequency
- Once daily
- Estimated price
- $35–70
- Website
- https://indiantrails.com
Bus from Escanaba, MI to Ironwood
- Ave. Duration
- 3h 40m
- Frequency
- Once daily
- Estimated price
- $30–55
- Website
- https://indiantrails.com
Bus from Duluth Transportation Center East to Hurley, WI
- Ave. Duration
- 2h 15m
- Frequency
- Once daily
- Estimated price
- $18–40
- Website
- https://indiantrails.com
Bus from Manitowoc, WI to Escanaba
- Ave. Duration
- 3h 35m
- Frequency
- Once daily
- Estimated price
- $25–50
- Website
- https://indiantrails.com
- Phone
- +1-858-800-8898
- Website
- jeffersonlines.com
Bus from St. Paul to Duluth
- Ave. Duration
- 2h 20m
- Frequency
- 3 times a day
- Estimated price
- $40–60
- Book at
- https://www.jeffersonlines.com
- Adult
- $40–60
Rome2Rio's guide to Greyhound USA
Contact Details
- Phone
- +1 214-849-8100
- ifsr@greyhound.com
- Website
- greyhound.com
Bus from Chicago Bus Station to Milwaukee Intermodal Station
- Ave. Duration
- 1h 40m
- Frequency
- 4 times a day
- Estimated price
- $14–28
- Website
- https://www.greyhound.com/
Bus from Chicago Bus Station to Manitowoc
- Ave. Duration
- 4h 15m
- Frequency
- Once daily
- Estimated price
- $27–55
- Website
- https://www.greyhound.com/
- Phone
- +1 (855) 626-8585
- Website
- https://www.flixbus.com
Bus from Chicago Bus Station to Milwaukee Intermodal Station
- Ave. Duration
- 1h 55m
- Frequency
- 3 times a day
- Estimated price
- $11–20
- Schedules at
- flixbus.com
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