Madison, WI → Chicago | Bus, Train Tickets | Search, Compare & Buy

Next bus departures

Next departures for Madison to Chicago on April 23
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Bus	2:20pm	Madison WI - Dutch Mill Park-N-Ride (SMD)	2h 55m	5:15pm	ORD Chicago O'Hare Airport Terminal 5	Cheapest
Bus	2:20pm	Madison WI - Dutch Mill Park-N-Ride (SMD)	2h 40m	5:00pm	Chicago O'Hare International Airport T2	Fastest
Bus	2:20pm	Dutch Mill Park & Ride	3h 55m	6:15pm	Chicago (Union Station), IL	No tags
Bus	1:25pm	North Lake St	4h 10m	5:35pm	Downtown Greyhound Station	No tags
Bus	3:20pm	Madison WI - Dutch Mill Park-N-Ride (SMD)	2h 55m	6:15pm	ORD Chicago O'Hare Airport Terminal 5	No tags

Next departures for Madison to Chicago on April 24
Operated by	Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
	Bus	1:25pm	North Lake St	4h 10m	5:35pm	Downtown Greyhound Station	Cheapest
	Bus	7:20am	Madison WI - Dutch Mill Park-N-Ride (SMD)	2h 40m	10:00am	Chicago O'Hare International Airport T2	Fastest
	Bus	1:45am	Dutch Mill Park & Ride	3h 35m	5:20am	Chicago (Union Station), IL	No tags
	Bus	6:45am	North Lake St	3h 10m	9:55am	Downtown Greyhound Station	No tags
FlixBus + Greyhound Lines, Inc.	Bus	5:55pm	North Lake St	5h 40m	11:35pm	Chicago 95Th & Dan Ryan	No tags

Next departures for Madison to Chicago on April 25
Operated by	Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
	Bus	6:45am	North Lake St	3h 10m	9:55am	Downtown Greyhound Station	Cheapest
	Bus	7:20am	Madison WI - Dutch Mill Park-N-Ride (SMD)	2h 40m	10:00am	Chicago O'Hare International Airport T2	Fastest
	Bus	1:45am	Dutch Mill Park & Ride	3h 35m	5:20am	Chicago (Union Station), IL	No tags
	Bus	1:25pm	North Lake St	4h 10m	5:35pm	Downtown Greyhound Station	No tags
FlixBus + Greyhound Lines, Inc.	Bus	5:55pm	North Lake St	5h 40m	11:35pm	Chicago 95Th & Dan Ryan	No tags

Next departures for Madison to Chicago on April 26
Operated by	Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
	Bus	6:45am	North Lake St	3h 10m	9:55am	Downtown Greyhound Station	Cheapest
	Bus	7:20am	Madison WI - Dutch Mill Park-N-Ride (SMD)	2h 40m	10:00am	Chicago O'Hare International Airport T2	Fastest
	Bus	1:45am	Dutch Mill Park & Ride	3h 35m	5:20am	Chicago (Union Station), IL	No tags
	Bus	1:25pm	North Lake St	4h 10m	5:35pm	Downtown Greyhound Station	No tags
FlixBus + Greyhound Lines, Inc.	Bus	5:55pm	North Lake St	5h 40m	11:35pm	Chicago 95Th & Dan Ryan	No tags

Next departures for Madison to Chicago on April 27
Operated by	Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
	Bus	6:45am	North Lake St	3h 10m	9:55am	Downtown Greyhound Station	Cheapest
	Bus	7:20am	Madison WI - Dutch Mill Park-N-Ride (SMD)	2h 40m	10:00am	Chicago O'Hare International Airport T2	Fastest
	Bus	1:45am	Dutch Mill Park & Ride	3h 35m	5:20am	Chicago (Union Station), IL	No tags
	Bus	1:25pm	North Lake St	4h 10m	5:35pm	Downtown Greyhound Station	No tags
FlixBus + Greyhound Lines, Inc.	Bus	5:55pm	North Lake St	5h 40m	11:35pm	Chicago 95Th & Dan Ryan	No tags

Next departures for Madison to Chicago on April 28
Operated by	Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
	Bus	5:55pm	North Lake St	3h 40m	9:35pm	Downtown Greyhound Station	Cheapest
	Bus	7:20am	Madison WI - Dutch Mill Park-N-Ride (SMD)	2h 40m	10:00am	Chicago O'Hare International Airport T2	Fastest
	Bus	1:45am	Dutch Mill Park & Ride	3h 35m	5:20am	Chicago (Union Station), IL	No tags
	Bus	6:45am	North Lake St	3h 10m	9:55am	Downtown Greyhound Station	No tags
FlixBus + Greyhound Lines, Inc.	Bus	5:55pm	North Lake St	5h 40m	11:35pm	Chicago 95Th & Dan Ryan	No tags

Next departures for Madison to Chicago on April 29
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Bus	1:25pm	North Lake St	4h 10m	5:35pm	Downtown Greyhound Station	Cheapest
Bus	7:20am	Madison WI - Dutch Mill Park-N-Ride (SMD)	2h 40m	10:00am	Chicago O'Hare International Airport T2	Fastest
Bus	1:45am	Dutch Mill Park & Ride	3h 35m	5:20am	Chicago (Union Station), IL	No tags
Bus	1:45pm	Dutch Mill Park & Ride	3h 50m	5:35pm	Downtown Greyhound Station	No tags
Bus	1:45am	Madison WI - Dutch Mill Park-N-Ride (SMD)	3h	4:45am	ORD Chicago O'Hare Airport Terminal 5	No tags

Next departures for Madison to Chicago on April 30
Operated by	Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
	Bus	6:45am	North Lake St	3h 10m	9:55am	Downtown Greyhound Station	Cheapest
	Bus	7:20am	Madison WI - Dutch Mill Park-N-Ride (SMD)	2h 40m	10:00am	Chicago O'Hare International Airport T2	Fastest
	Bus	1:45am	Dutch Mill Park & Ride	3h 35m	5:20am	Chicago (Union Station), IL	No tags
	Bus	1:25pm	North Lake St	4h 10m	5:35pm	Downtown Greyhound Station	No tags
FlixBus + Greyhound Lines, Inc.	Bus	5:55pm	North Lake St	5h 40m	11:35pm	Chicago 95Th & Dan Ryan	No tags

Last refresh of the prices: Today at 7:40 AM CDT.

Find cheapest prices for buses

Price is for a one-way ticket for one passenger and based on past searches.

Best price found

04/21

MAD 363

04/22

MAD 343

Today

MAD 343

04/24

MAD 305

04/25

MAD 233

04/26

MAD 295

04/27

MAD 295

04/28

MAD 214

The cheapest trip from Madison, WI to Chicago was searched and found on Apr 28, 2026 with a price of MAD 214

To save money and be sure you have the best seat, it's a good idea to buy your bus tickets from Madison, WI to Chicago, as early as possible.

You can expect to pay from MAD 214 to MAD 1,702 for a bus ticket from Madison, WI to Chicago based on the last 2 days. You can expect to find the cheapest price for the trip at MAD 214 which is on 2026-04-28.

Usually Jefferson Lines will charge you higher prices for tickets closer to the departure date. To find the best prices, you should be flexible on your date of travel.