There are 10 ways to get from Madisonville to Chicago by taxi, plane, bus, train, bus (Greyhound, Amtrak), car, or bus (Greyhound, Flixbus)
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Taxi to Owensboro–Daviess County Regional Airport, fly to Chicago O'Hare International Airport
best- Take the taxi from Madisonville to Owensboro–Daviess County Regional Airport (OWB)taxi
- Fly from Owensboro–Daviess County Regional Airport (OWB) to Chicago O'Hare International Airport (ORD)plane OWB - ORD
3h 33m$139–283Drive 332.1 mi
cheapest- Drive from Madisonville to Chicagocar 332.1 mi
6h 49m$61–88Bus, train
- Take the bus from Madisonville to St Louis Bus Stationbus Greyhound US0185
- Take the train from St. Louis to Chicago Union Stationtrain Lincoln Service / ...
10h 49m$93–211Bus
- Take the bus from Madisonville to Evansville Bus Stationbus
- Take the bus from Evansville, IN to Indianapolis Union Stationbus
- Take the bus from Indianapolis Union Station to Chicago Union Stationbus
11h 19m$132–221Drive to Williamson County Regional Airport, fly to Chicago O'Hare International Airport
- Drive from Madisonville to Williamson County Regional Airport (MWA)car
- Fly from Williamson County Regional Airport (MWA) to Chicago O'Hare International Airport (ORD)plane MWA - ORD
4h 41m$75–201Drive to Barkley Regional Airport, fly to Chicago O'Hare International Airport
- Drive from Madisonville to Barkley Regional Airport (PAH)car
- Fly from Barkley Regional Airport (PAH) to Chicago O'Hare International Airport (ORD)plane PAH - ORD
4h 9m$207–727Bus to Evansville, fly to Chicago O'Hare International Airport
- Take the bus from Madisonville to Evansville Bus Stationbus
- Fly from Evansville (EVV) to Chicago O'Hare International Airport (ORD)plane EVV - ORD
5h 1m$105–396Bus to Nashville, fly to Chicago Midway International Airport
- Take the bus from Madisonville to Nashville Bus Stationbus
- Fly from Nashville (BNA) to Chicago Midway International Airport (MDW)plane BNA - MDW
6h 14m$106–468Bus via Bloomington
- Take the bus from Madisonville to Evansville Bus Stationbus
- Take the bus from Evansville, IN to Bloomington, INbus
- Take the bus from Bloomington to Chicago Bus Stationbus
11h 54m$117–211Bus, train via Indianapolis
- Take the bus from Madisonville to Evansville Bus Stationbus
- Take the bus from Evansville, IN to Indianapolis Union Stationbus
- Take the train from Indianapolis to Chicago Union Stationtrain
12h 39m$127–216
Owensboro–Daviess County Regional Airport (OWB) to Chicago O'Hare International Airport (ORD) flights
Questions & Answers
The cheapest way to get from Madisonville to Chicago is to drive which costs $60 - $90 and takes 6h 49m.
The fastest way to get from Madisonville to Chicago is to taxi and fly which takes 3h 33m and costs $130 - $290.
The distance between Madisonville and Chicago is 356 miles. The road distance is 334.1 miles.
The best way to get from Madisonville to Chicago without a car is to bus and train which takes 10h 49m and costs $90 - $220.
It takes approximately 3h 33m to get from Madisonville to Chicago, including transfers.
Yes, the driving distance between Madisonville to Chicago is 334 miles. It takes approximately 6h 49m to drive from Madisonville to Chicago.
There are 1272+ hotels available in Chicago.
What companies run services between Madisonville, KY, USA and Chicago, IL, USA?
You can take a vehicle from Madisonville to Chicago Union Station via Madisonville, Evansville, IN, and Indianapolis Union Station in around 11h 19m.
- Website
- southwest.com
Flights from Nashville to Chicago Midway International Airport
- Ave. Duration
- 1h 38m
- When
- Every day
- Estimated price
- $55–380
Flights from Nashville to Chicago Midway International Airport via Louisville
- Ave. Duration
- 3h 35m
- When
- Monday and Sunday
- Estimated price
- $60–390
Flights from Nashville to Chicago Midway International Airport via Indianapolis
- Ave. Duration
- 3h 40m
- When
- Monday, Tuesday, Wednesday, and Sunday
- Estimated price
- $60–380
- Website
- contouraviation.com
Flights from Owensboro–Daviess County Regional Airport to Chicago O'Hare International Airport
- Ave. Duration
- 1h 35m
- When
- Every day
- Estimated price
- $45–170
Flights from Williamson County Regional Airport to Chicago O'Hare International Airport
- Ave. Duration
- 1h 35m
- When
- Every day
- Estimated price
- $55–170
- Website
- aa.com
Flights from Evansville to Chicago O'Hare International Airport
- Ave. Duration
- 1h 52m
- When
- Every day
- Estimated price
- $40–290
- Website
- united.com
Flights from Barkley Regional Airport to Chicago O'Hare International Airport
- Ave. Duration
- 1h 45m
- When
- Monday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $75–500
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from St. Louis to Chicago Union Station
- Ave. Duration
- 4h 55m
- Frequency
- 5 times a day
- Estimated price
- $35–110
- Website
- https://www.amtrak.com/home.html
Train from Indianapolis to Chicago Union Station
- Ave. Duration
- 5h
- Frequency
- 3 times a week
- Estimated price
- $30–65
- Website
- https://www.amtrak.com/home.html
Rome2Rio's guide to Greyhound USA
Contact Details
- Phone
- +1 214-849-8100
- ifsr@greyhound.com
- Website
- greyhound.com
Bus from Madisonville to St Louis Bus Station
- Ave. Duration
- 4h 45m
- Frequency
- Once daily
- Estimated price
- $40–80
- Website
- https://www.greyhound.com/
Bus from Madisonville to Evansville Bus Station
- Ave. Duration
- 1h
- Frequency
- Once daily
- Estimated price
- $24–55
- Website
- https://www.greyhound.com/
Bus from Indianapolis Union Station to Chicago Union Station
- Ave. Duration
- 3h 50m
- Frequency
- Twice daily
- Estimated price
- $35–70
- Website
- https://www.greyhound.com/
Bus from Madisonville to Nashville Bus Station
- Ave. Duration
- 2h 5m
- Frequency
- Once daily
- Estimated price
- $29–60
- Website
- https://www.greyhound.com/
- Phone
- +1 502-368-5644 x 135
- Website
- ridewithmiller.com
Bus from Evansville, IN to Indianapolis Union Station
- Ave. Duration
- 4h 30m
- Frequency
- Once daily
- Estimated price
- $55–75
- Website
- https://ridewithmiller.com
Bus from Evansville, IN to Bloomington, IN
- Ave. Duration
- 3h 15m
- Frequency
- Once daily
- Estimated price
- $40–60
- Website
- https://ridewithmiller.com
Rome2Rio's guide to Amtrak Thruway
Contact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Bus from Indianapolis Union Station to Chicago Union Station
- Ave. Duration
- 3h 40m
- Frequency
- Twice daily
- Estimated price
- $35–50
- Website
- https://www.amtrak.com/home.html
- Adult
- $35–50
- Phone
- +1 (855) 626-8585
- Website
- flixbus.com
Bus from Bloomington to Chicago Bus Station
- Ave. Duration
- 5h 30m
- Frequency
- Twice daily
- Estimated price
- $35–75
- Schedules at
- flixbus.com
- Ave. Duration
- 1h 11m
- Estimated price
- $90–110
Want to know more about travelling around United States
Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.
Related travel guides
Travelling to the US: What do I need to know?
Read the travel guide
Need to know: Greyhound
Read the travel guide
Why you should take the train in the US
Read the travel guide













