There are 7 ways to get from Chicago to Shepherdsville by subway, 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.
Subway to Chicago Midway International Airport, fly to Louisville International Airport
best- Take the subway from Roosevelt to Midwaysubway
- Fly from Chicago Midway International Airport (MDW) to Louisville International Airport (SDF)plane MDW - SDF
2h 59m$132–665Drive 313.6 mi
cheapest- Drive from Chicago to Shepherdsvillecar 313.6 mi
5h 24m$58–83Bus (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$121–214Fly 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 30m$288–515Fly Chicago O'Hare International Airport to Blue Grass Airport, drive
- Fly from Chicago O'Hare International Airport (ORD) to Blue Grass Airport (LEX)plane ORD - LEX
- Drive from Lexington-Airport-LEX to Shepherdsvillecar
4h 41m$100–625Bus 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$100–222
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 subway and fly which takes 2h 59m and costs $130 - $700.
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 2h 59m to get from Chicago to Shepherdsville, including transfers.
The best way to get from Chicago to Shepherdsville is to bus which takes 8h 25m and costs $100 - $120. Alternatively, you can fly, which costs $280 - $550 and takes 3h 30m.
Shepherdsville is 1h ahead of Chicago. It is currently 1:35 PM in Chicago and 2:35 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 23+ hotels available in Shepherdsville.
What companies run services between Chicago, IL, USA and Shepherdsville, KY, USA?
Amtrak Thruway operates a bus from Chicago Union Station to Louisville, KY twice daily. Tickets cost $50–60 and the journey takes 7h. Alternatively, American Airlines and United Airlines fly from Chicago O'Hare International Airport (ORD) to Louisville International Airport (SDF) every 3 hours.
- Website
- aa.com
Flights from Chicago O'Hare International Airport to Louisville International Airport
- Ave. Duration
- 1h 27m
- When
- Every day
- Estimated price
- $55–380
Flights from Chicago O'Hare International Airport to Blue Grass Airport
- Ave. Duration
- 1h 24m
- When
- Every day
- Estimated price
- $85–600
- Website
- united.com
Flights from Chicago O'Hare International Airport to Louisville International Airport
- Ave. Duration
- 1h 29m
- When
- Every day
- Estimated price
- $55–380
Flights from Chicago O'Hare International Airport to Blue Grass Airport
- Ave. Duration
- 1h 29m
- When
- Every day
- Estimated price
- $85–600
- Website
- southwest.com
Flights from Chicago Midway International Airport to Louisville International Airport
- Ave. Duration
- 1h 14m
- When
- Every day
- Estimated price
- $85–600
- Phone
- +1 888-968-7282
- Website
- transitchicago.com
Subway from Roosevelt to Midway
- Ave. Duration
- 20 min
- Frequency
- Every 10 minutes
- Estimated price
- $2–5
- Website
- https://www.transitchicago.com
- Schedules at
- https://www.transitchicago.com/schedules/
- Adult
- $2–5
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
- $40–100
- 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
- $21–40
- 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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