There are 9 ways to get from Kentucky to Chicago by plane, bus (Amtrak), bus, train, 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 Owensboro–Daviess County Regional Airport to Chicago O'Hare International Airport
best- Fly from Owensboro–Daviess County Regional Airport (OWB) to Chicago O'Hare International Airport (ORD)plane OWB - ORD
2h 30m$63–188Bus (Amtrak)
cheapest- Take the bus from Louisville, KY to Chicago Union Stationbus
6h$50–60Bus, train (Amtrak)
- Take the bus from Louisville, KY to Indianapolis Union Stationbus
- Take the train from Indianapolis to Chicago Union Stationtrain Cardinal
8h 20m$58–109Drive 294.4 mi
- Drive from Louisville to Chicagocar 294.4 mi
5h 2m$54–78Fly Blue Grass Airport to Chicago O'Hare International Airport
- Fly from Blue Grass Airport (LEX) to Chicago O'Hare International Airport (ORD)plane LEX - ORD
2h 48m$68–292Fly Louisville International Airport to Chicago Midway International Airport
- Fly from Louisville International Airport (SDF) to Chicago Midway International Airport (MDW)plane SDF - MDW
3h 30m$64–438Fly Louisville International Airport to Chicago O'Hare International Airport
- Fly from Louisville International Airport (SDF) to Chicago O'Hare International Airport (ORD)plane SDF - ORD
4h 4m$194–558Fly Covington to Chicago O'Hare International Airport
- Fly from Covington (CVG) to Chicago O'Hare International Airport (ORD)plane CVG - ORD
3h 58m$58–396Fly Covington to Chicago Midway International Airport
- Fly from Covington (CVG) to Chicago Midway International Airport (MDW)plane CVG - MDW
3h 30m$84–556
Kentucky to Chicago by bus (Amtrak)
Questions & Answers
The cheapest way to get from Kentucky to Chicago is to bus which costs $50 - $60 and takes 6h.
The fastest way to get from Kentucky to Chicago is to fly which takes 2h 30m and costs $60 - $190.
Yes, there is a direct bus departing from Louisville, KY and arriving at Chicago Union Station station. Services depart twice daily, and operate every day. The journey takes approximately 6h.
The distance between Kentucky and Chicago is 319 miles. The road distance is 296.1 miles.
The best way to get from Kentucky to Chicago without a car is to bus which takes 6h and costs $50 - $60.
It takes approximately 2h 30m to get from Kentucky to Chicago, including transfers.
Kentucky to Chicago bus services, operated by Amtrak Thruway, depart from Louisville, KY station.
The best way to get from Kentucky to Chicago is to fly which takes 2h 30m and costs $60 - $190. Alternatively, you can bus, which costs $50 - $60 and takes 6h.
Kentucky to Chicago bus services, operated by Amtrak Thruway, arrive at Chicago Union Station.
Chicago is 1h behind Kentucky. It is currently 4:41 AM in Kentucky and 3:41 AM in Chicago.
What companies run services between Kentucky, USA and Chicago, IL, USA?
Corporate Flight Management Inc flies from Owensboro–Daviess County Regional Airport (OWB) to Chicago O'Hare International Airport (ORD) twice daily. Alternatively, Amtrak Thruway operates a bus from Louisville, KY to Chicago Union Station twice daily. Tickets cost $50–60 and the journey takes 6h.
- Website
- united.com
Flights from Blue Grass Airport to Chicago O'Hare International Airport
- Ave. Duration
- 1h 55m
- When
- Every day
- Estimated price
- $35–250
Flights from Louisville International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 1h 43m
- When
- Every day
- Estimated price
- $40–300
Flights from Covington to Chicago O'Hare International Airport
- Ave. Duration
- 1h 38m
- When
- Every day
- Estimated price
- $55–390
- Website
- aa.com
Flights from Blue Grass Airport to Chicago O'Hare International Airport
- Ave. Duration
- 1h 50m
- When
- Every day
- Estimated price
- $35–250
Flights from Louisville International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 1h 51m
- When
- Every day
- Estimated price
- $40–300
Flights from Covington to Chicago O'Hare International Airport
- Ave. Duration
- 1h 36m
- When
- Every day
- Estimated price
- $55–390
- Website
- southwest.com
Flights from Louisville International Airport to Chicago Midway International Airport
- Ave. Duration
- 1h 22m
- When
- Every day
- Estimated price
- $60–430
Flights from Louisville International Airport to Chicago Midway International Airport via Nashville
- Ave. Duration
- 3h 30m
- When
- Saturday
- Estimated price
- $85–500
Flights from Covington to Chicago Midway International Airport
- Ave. Duration
- 1h 15m
- When
- Every day
- Estimated price
- $80–550
- 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
- $50–170
- Website
- delta.com
Flights from Blue Grass Airport to Chicago O'Hare International Airport via Detroit
- Ave. Duration
- 4h 30m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $45–280
Flights from Covington to Chicago O'Hare International Airport via Detroit
- Ave. Duration
- 3h 35m
- When
- Every day
- Estimated price
- $70–430
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Indianapolis to Chicago Union Station
- Ave. Duration
- 5h
- Frequency
- 3 times a week
- Estimated price
- $35–65
- Website
- https://www.amtrak.com/home.html
Rome2Rio's guide to Amtrak Thruway
Contact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Bus from Louisville, KY to Chicago Union Station
- Ave. Duration
- 6h
- Frequency
- Twice daily
- Estimated price
- $50–60
- Website
- https://www.amtrak.com/home.html
- Adult
- $50–60
Bus from Louisville, KY to Indianapolis Union Station
- Ave. Duration
- 2h 20m
- Frequency
- Twice daily
- Estimated price
- $22–45
- Website
- https://www.amtrak.com/home.html
- Adult
- $22–45
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More Questions & Answers
Yes, the driving distance between Kentucky to Chicago is 296 miles. It takes approximately 5h 2m to drive from Kentucky to Chicago.
Book your Kentucky to Chicago bus tickets online with Omio.
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