There are 7 ways to get from Chicago to Shepherdsville by plane, bus (Amtrak), train, bus, car, or bus (Flixbus)
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Fly Chicago Midway International Airport to Louisville International Airport
best- Fly from Chicago Midway International Airport (MDW) to Louisville International Airport (SDF)plane MDW - SDF
3h 4m$122–615Fly Chicago O'Hare International Airport to Blue Grass Airport, drive
cheapest- Fly from Chicago O'Hare International Airport (ORD) to Blue Grass Airport (LEX)plane ORD - LEX
- Drive from Lexington-Airport-LEX to Shepherdsvillecar
4h 43m$56–305Bus (Amtrak)
- Take the bus from Chicago Union Station to Louisville, KYbus Chicago
8h 25m$101–119Train, bus (Amtrak)
- Take the train from Chicago Union Station to Indianapolistrain Cardinal
- Take the bus from Indianapolis Union Station to Louisville, KYbus Chicago
8h 43m$109–179Drive 313.6 mi
- Drive from Chicago to Shepherdsvillecar 313.6 mi
5h 24m$58–83Fly Chicago O'Hare International Airport to Louisville International Airport
- Fly from Chicago O'Hare International Airport (ORD) to Louisville International Airport (SDF)plane ORD - SDF
3h 36m$238–615Bus via Speedway
- Take the bus from Chicago Bus Station to Indianapolisbus FlixBus N2640 / ...
- Take the bus from Indianapolis to La Tropicana - Louisville, KYbus Indianapolis
9h 12m$114–251
Chicago Midway International Airport (MDW) to Louisville International Airport (SDF) flights
Questions & Answers
The cheapest way to get from Chicago to Shepherdsville is to drive which costs $55 - $85 and takes 5h 24m.
The fastest way to get from Chicago to Shepherdsville is to fly which takes 3h 4m and costs $120 - $650.
The distance between Chicago and Shepherdsville is 299 miles. The road distance is 315.5 miles.
The best way to get from Chicago to Shepherdsville without a car is to bus which takes 8h 25m and costs $100 - $120.
It takes approximately 3h 4m to get from Chicago to Shepherdsville, including transfers.
The best way to get from Chicago to Shepherdsville is to fly which takes 3h 4m and costs $120 - $650. Alternatively, you can bus, which costs $100 - $120 and takes 8h 25m.
Shepherdsville is 1h ahead of Chicago. It is currently 2:12 PM in Chicago and 3:12 PM in Shepherdsville.
Yes, the driving distance between Chicago to Shepherdsville is 315 miles. It takes approximately 5h 24m to drive from Chicago to Shepherdsville.
There are 19+ hotels available in Shepherdsville.
What companies run services between Chicago, IL, USA and Shepherdsville, KY, USA?
Southwest Airlines flies from Chicago Midway International Airport (MDW) to Louisville International Airport (SDF) twice daily. Alternatively, Amtrak Thruway operates a bus from Chicago Union Station to Louisville, KY twice daily. Tickets cost $50–60 and the journey takes 7h.
- Website
- united.com
Flights from Chicago O'Hare International Airport to Louisville International Airport
- Ave. Duration
- 1h 38m
- When
- Every day
- Estimated price
- $55–390
Flights from Chicago O'Hare International Airport to Blue Grass Airport
- Ave. Duration
- 1h 34m
- When
- Every day
- Estimated price
- $40–280
- Website
- aa.com
Flights from Chicago O'Hare International Airport to Louisville International Airport
- Ave. Duration
- 1h 30m
- When
- Every day
- Estimated price
- $55–390
Flights from Chicago O'Hare International Airport to Blue Grass Airport
- Ave. Duration
- 1h 28m
- When
- Every day
- Estimated price
- $40–280
- Website
- southwest.com
Flights from Chicago Midway International Airport to Louisville International Airport
- Ave. Duration
- 1h 15m
- When
- Every day
- Estimated price
- $75–550
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Chicago Union Station to Indianapolis
- Ave. Duration
- 4h 54m
- Frequency
- 3 times a week
- Estimated price
- $30–65
- 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 Chicago Union Station to Louisville, KY
- Ave. Duration
- 7h
- Frequency
- Twice daily
- Estimated price
- $50–60
- Website
- https://www.amtrak.com/home.html
- Adult
- $50–60
Bus from Indianapolis Union Station to Louisville, KY
- Ave. Duration
- 2h 25m
- Frequency
- Twice daily
- Estimated price
- $22–45
- Website
- https://www.amtrak.com/home.html
- Adult
- $22–45
- Phone
- +1 (855) 626-8585
- Website
- flixbus.com
Bus from Chicago Bus Station to Indianapolis
- Ave. Duration
- 3h 50m
- Frequency
- Every 4 hours
- Estimated price
- $35–70
- Schedules at
- flixbus.com
- Phone
- +1 888 358 6762
- info@tornadobus.com
- Website
- tornadobus.com
Bus from Indianapolis to La Tropicana - Louisville, KY
- Ave. Duration
- 2h 31m
- Frequency
- 3 times a week
- Estimated price
- $45–140
- Schedules at
- tornadobus.com
- Adults 11-59
- $45–140
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