There are 6 ways to get from Shepherdsville 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 Louisville International Airport to Chicago Midway International Airport
best- Fly from Louisville International Airport (SDF) to Chicago Midway International Airport (MDW)plane SDF - MDW
2h 15m$111–492Drive to Blue Grass Airport, fly to Chicago O'Hare International Airport
cheapest- Drive from Shepherdsville to Lexington-Airport-LEXcar
- Fly from Blue Grass Airport (LEX) to Chicago O'Hare International Airport (ORD)plane LEX - ORD
4h 5m$50–274Bus (Amtrak)
- Take the bus from Louisville, KY to Chicago Union Stationbus
6h 24m$108–129Bus, train (Amtrak)
- Take the bus from Louisville, KY to Indianapolis Union Stationbus
- Take the train from Indianapolis to Chicago Union Stationtrain Cardinal
8h 44m$115–189Drive 314.7 mi
- Drive from Shepherdsville to Chicagocar 314.7 mi
5h 23m$58–83Fly 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
2h 49m$241–612
Louisville International Airport (SDF) to Chicago Midway International Airport (MDW) flights
Questions & Answers
The cheapest way to get from Shepherdsville to Chicago is to drive which costs $55 - $85 and takes 5h 23m.
The fastest way to get from Shepherdsville to Chicago is to fly which takes 2h 15m and costs $110 - $500.
The distance between Shepherdsville and Chicago is 300 miles. The road distance is 316.6 miles.
The best way to get from Shepherdsville to Chicago without a car is to bus which takes 6h 24m and costs $100 - $130.
It takes approximately 2h 15m to get from Shepherdsville to Chicago, including transfers.
The best way to get from Shepherdsville to Chicago is to fly which takes 2h 15m and costs $110 - $500. Alternatively, you can bus, which costs $100 - $130 and takes 6h 24m.
Chicago is 1h behind Shepherdsville. It is currently 5:00 PM in Shepherdsville and 4:00 PM in Chicago.
Yes, the driving distance between Shepherdsville to Chicago is 317 miles. It takes approximately 5h 23m to drive from Shepherdsville to Chicago.
There are 1241+ hotels available in Chicago.
What companies run services between Shepherdsville, KY, USA and Chicago, IL, USA?
Southwest Airlines flies from Louisville International Airport (SDF) to Chicago Midway International Airport (MDW) 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 Louisville International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 1h 43m
- When
- Every day
- Estimated price
- $40–300
Flights from Blue Grass Airport to Chicago O'Hare International Airport
- Ave. Duration
- 1h 55m
- When
- Every day
- Estimated price
- $35–250
- 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
- Website
- aa.com
Flights from Louisville International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 1h 51m
- When
- Every day
- Estimated price
- $40–300
Flights from Blue Grass Airport to Chicago O'Hare International Airport
- Ave. Duration
- 1h 50m
- When
- Every day
- Estimated price
- $35–250
- 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
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
- $35–75
- 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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