There are 5 ways to get from Chicago to Madison by plane, bus (Greyhound), train (Amtrak), car, or taxi
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 Charlottesville
best- Fly from Chicago O'Hare International Airport (ORD) to Charlottesville (CHO)plane ORD - CHO
4h 21m$128–410Drive 686.6 mi
cheapest- Drive from Chicago to Madisoncar 686.6 mi
12h 21m$126–181Bus
- Take the bus from Chicago Bus Station to Washington Union Stationbus
- Take the bus from Washington Union Station to Charlottesville Union Stationbus
- Take the bus from Charlottesville City Bus Hub to Madison - Food Lionbus
23h 20mTrain (Amtrak)
- Take the train from Chicago Union Station to Culpeper Amtrak Stationtrain Cardinal
23h 35m$460–750Fly to Shenandoah Valley Regional Airport, taxi
- Fly from Chicago O'Hare International Airport (ORD) to Shenandoah Valley Regional Airport (SHD)plane ORD - SHD
- Take the taxi from Shenandoah Valley Regional Airport (SHD) to Madisontaxi
5h 5m$152–435
Chicago O'Hare International Airport (ORD) to Charlottesville (CHO) flights
Comparing Your Travel Options
The cheapest way to get from Chicago to Madison is to drive which costs $120 - $190 and takes 12h 21m.
The fastest way to get from Chicago to Madison is to fly which takes 4h 21m and costs $120 - $410.
No, there is no direct bus from Chicago station to Madison. However, there are services departing from Chicago Bus Station and arriving at Madison - Food Lion via Washington Union Station, W Main St at The Flats and Charlottesville City Bus Hub. The journey, including transfers, takes approximately 23h 20m.
No, there is no direct train from Chicago station to Madison station. However, there are services departing from Chicago Union Station and arriving at Culpeper Amtrak Station via . The journey, including transfers, takes approximately 23h 35m.
The distance between Chicago and Madison is 608 miles. The road distance is 690.6 miles.
The best way to get from Chicago to Madison without a car is to bus which takes 23h 20m and costs .
It takes approximately 4h 21m to get from Chicago to Madison, including transfers.
Chicago to Madison bus services, operated by Greyhound USA, depart from Chicago Bus Station.
Chicago to Madison train services, operated by Amtrak, depart from Chicago Union Station.
The best way to get from Chicago to Madison is to fly which takes 4h 21m and costs $120 - $410. Alternatively, you can bus, which costs and takes 23h 20m, you could also train, which costs $460 - $750 and takes 23h 35m.
What companies run services between Chicago, IL, USA and Madison, VA, USA?
American Airlines, United Airlines, and Delta fly from Chicago O'Hare International Airport (ORD) to Charlottesville (CHO) every 2 hours. Alternatively, you can take a bus from Chicago Bus Station to Madison - Food Lion via Washington Union Station, Charlottesville Union Station, W Main St at The Flats, and Charlottesville City Bus Hub in around 23h 20m.
- Website
- aa.com
Flights from Chicago O'Hare International Airport to Charlottesville
- Ave. Duration
- 2h 10m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $55–320
Flights from Chicago O'Hare International Airport to Charlottesville via Charlotte
- Ave. Duration
- 4h 45m
- When
- Every day
- Estimated price
- $70–360
Flights from Chicago O'Hare International Airport to Shenandoah Valley Regional Airport
- Ave. Duration
- 2h 6m
- When
- Every day
- Estimated price
- $50–310
- Website
- united.com
Flights from Chicago O'Hare International Airport to Charlottesville
- Ave. Duration
- 2h 10m
- When
- Every day
- Estimated price
- $55–320
Flights from Chicago O'Hare International Airport to Charlottesville via Washington Dulles
- Ave. Duration
- 4h 43m
- When
- Every day
- Estimated price
- $60–340
- Website
- delta.com
Flights from Chicago O'Hare International Airport to Charlottesville via Atlanta
- Ave. Duration
- 5h
- When
- Every day
- Estimated price
- $80–400
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Chicago Union Station to Culpeper Amtrak Station
- Ave. Duration
- 22h 5m
- Frequency
- 3 times a week
- Estimated price
- $460–750
- Website
- Amtrak
Rome2Rio's guide to Greyhound USA
Contact DetailsContact Details
- Phone
- +1 214-849-8100
- ifsr@greyhound.com
- Website
- Greyhound
Bus from Chicago Bus Station to Washington Union Station
- Ave. Duration
- 16h 35m
- Frequency
- Twice daily
- Estimated price
- $110–190
- Website
- Greyhound
Bus from Washington Union Station to Charlottesville Union Station
- Ave. Duration
- 3h 30m
- Frequency
- Once daily
- Estimated price
- $20–35
- Website
- Greyhound
- Phone
- +1 877-777-2708
- support@vatransit.org
- Website
- Virginia Regional Transit
Bus from Charlottesville City Bus Hub to Madison - Food Lion
- Ave. Duration
- 55 min
- Frequency
- Once daily
- Website
- Virginia Regional Transit
- Ave. Duration
- 1h 14m
- Estimated price
- $100–120
1st Call Taxi
- Phone
- +1 540-849-5348
- Website
- 1stcalltaxi.wordpress.com
ABC Cab Co.
- Phone
- +1 540-564-1214
- Website
- abccabcova.com
Checkered Cab Co
- Phone
- +1 540-908-2838
- Website
- facebook.com
Want to know more about travelling around United States
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Chicago to Madison bus services, operated by Greyhound USA, arrive at Washington Union Station.
Madison is 1h ahead of Chicago. It is currently 00:51 in Chicago and 01:51 in Madison.
Chicago to Madison train services, operated by Amtrak, arrive at Culpeper Amtrak Station.
Yes, the driving distance between Chicago to Madison is 691 miles. It takes approximately 12h 21m to drive from Chicago to Madison.
There are 39+ hotels available in Madison.