There are 5 ways to get from Chicago to Madison by plane, bus (Greyhound, Flixbus), train (Amtrak), or car
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Fly from Chicago Midway International Airport
best- Fly from Chicago Midway International Airport (MDW) to Jackson/Vicksburg (JAN)plane MDW - JAN
5h 38m$168–580Drive 727.1 mi
cheapest- Drive from Chicago to Madisoncar 727.1 mi
11h 46m$133–192Bus
- Take the bus from Chicago Bus Station to Memphis Bus Stationbus Greyhound US0125
- Take the bus from Memphis Bus Station to Jacksonbus Greyhound US1173
15h 26m$145–264Train (Amtrak)
- Take the train from Chicago Union Station to Jacksontrain City of New Orleans
15h 54m$296–557Fly from Chicago O'Hare International Airport
- Fly from Chicago O'Hare International Airport (ORD) to Jackson/Vicksburg (JAN)plane ORD - JAN
6h 30m$162–520
Chicago Midway International Airport (MDW) to Jackson/Vicksburg (JAN) flights
Questions & Answers
The cheapest way to get from Chicago to Madison is to drive which costs $130 - $200 and takes 11h 46m.
The fastest way to get from Chicago to Madison is to fly which takes 5h 38m and costs $160 - $600.
No, there is no direct bus from Chicago station to Madison. However, there are services departing from Chicago Bus Station and arriving at Briarwood @ Hampton Inn via Memphis Bus Station and Union Station. The journey, including transfers, takes approximately 15h 26m.
No, there is no direct train from Chicago station to Madison. However, there are services departing from Chicago Union Station and arriving at Jackson via . The journey, including transfers, takes approximately 15h 54m.
The distance between Chicago and Madison is 700 miles. The road distance is 731.3 miles.
The best way to get from Chicago to Madison without a car is to bus which takes 15h 26m and costs $140 - $270.
It takes approximately 5h 38m 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 5h 38m and costs $160 - $600. Alternatively, you can bus, which costs $140 - $270 and takes 15h 26m, you could also train, which costs $290 - $600 and takes 15h 54m.
What companies run services between Chicago, IL, USA and Madison, MS, USA?
Southwest Airlines and Delta fly from Chicago Midway International Airport (MDW) to Jackson/Vicksburg (JAN) 5 times a day. Alternatively, you can take a bus from Chicago Bus Station to Madison via Memphis Bus Station, Union Station, and Briarwood @ Hampton Inn in around 15h 26m.
- Website
- delta.com
Flights from Chicago Midway International Airport to Jackson/Vicksburg via Atlanta
- Ave. Duration
- 5h 43m
- When
- Every day
- Estimated price
- $110–550
Flights from Chicago O'Hare International Airport to Jackson/Vicksburg via Atlanta
- Ave. Duration
- 4h 52m
- When
- Every day
- Estimated price
- $90–430
- Website
- aa.com
Flights from Chicago O'Hare International Airport to Jackson/Vicksburg via Dallas/Ft.Worth
- Ave. Duration
- 5h 36m
- When
- Every day
- Estimated price
- $100–480
Flights from Chicago O'Hare International Airport to Jackson/Vicksburg via Charlotte
- Ave. Duration
- 5h 58m
- When
- Every day
- Estimated price
- $100–470
Flights from Chicago O'Hare International Airport to Jackson/Vicksburg via Reagan Washington
- Ave. Duration
- 8h 11m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $120–550
- Website
- southwest.com
Flights from Chicago Midway International Airport to Jackson/Vicksburg via Nashville
- Ave. Duration
- 4h 42m
- When
- Tuesday, Wednesday, and Saturday
- Estimated price
- $95–490
Flights from Chicago Midway International Airport to Jackson/Vicksburg via Houston Hobby Apt
- Ave. Duration
- 5h 28m
- When
- Tuesday to Friday
- Estimated price
- $140–650
Flights from Chicago Midway International Airport to Jackson/Vicksburg via Indianapolis, Nashville
- Ave. Duration
- 7h 50m
- When
- Monday, Thursday, and Friday
- Estimated price
- $95–490
- Website
- united.com
Flights from Chicago O'Hare International Airport to Jackson/Vicksburg via Houston
- Ave. Duration
- 6h 2m
- When
- Every day
- Estimated price
- $110–490
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Chicago Union Station to Jackson
- Ave. Duration
- 15h 35m
- Frequency
- Once daily
- Estimated price
- $240–500
- Website
- https://www.amtrak.com/home.html
Rome2Rio's guide to Greyhound USA
Contact DetailsContact Details
- Phone
- +1 214-849-8100
- [email protected]
- Website
- greyhound.com
Bus from Chicago Bus Station to Memphis Bus Station
- Ave. Duration
- 9h 20m
- Frequency
- Once daily
- Estimated price
- $85–170
- Website
- https://www.greyhound.com/
Bus from Memphis Bus Station to Jackson
- Ave. Duration
- 3h 55m
- Frequency
- Once daily
- Estimated price
- $30–65
- Website
- https://www.greyhound.com/
- Phone
- +1 (855) 626-8585
- Website
- https://www.flixbus.com
Bus from Chicago Bus Station to Memphis Bus Station
- Ave. Duration
- 11h
- Frequency
- Once daily
- Estimated price
- $85–140
- Schedules at
- flixbus.com
Want to know more about travelling around United States
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More Questions & Answers
Chicago to Madison bus services, operated by Greyhound USA, arrive at Memphis Bus Station.
Chicago to Madison train services, operated by Amtrak, arrive at Jackson station.
Yes, the driving distance between Chicago to Madison is 731 miles. It takes approximately 11h 46m to drive from Chicago to Madison.
Book your Chicago to Madison train tickets online with Omio.
There are 118+ hotels available in Madison.