The cheapest and fastest trains from South Shore, KY to Chicago, IL
Cheapest price
$146
Average price
$146
Fastest journey
11 h 3 m
Average duration
11 h 3 m
Trains per day
1
Distance
528 km
The best way to find a cheap train ticket from South Shore, KY to Chicago, IL is to book your journey as far in advance as possible and to avoid traveling at rush hour.
The average ticket from South Shore, KY to Chicago, IL will cost around $146 if you buy it on the day, but the cheapest tickets can be found for only $146.
Of the 1 trains that leave South Shore, KY for Chicago, IL on Fri, Nov 28, 1 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Fri, Nov 28 the direct trains cover the 528 km distance in an average of 11 h 3 m but if you time it right, some trains will get you there in just 11 h 3 m .
On Fri, Nov 28 the slowest trains will take 11 h 3 m and usually involve a change or two along the way, but you might be able to save a few pennies if you’re on a budget.


Travel Information
Compare train and flight for South Shore, KY to Chicago, IL
Omio recommends booking the train as it is the most popular option from South Shore, KY to Chicago, IL among Omio's users. If you are prioritising price take the train with prices starting from €119. For those with little time consider booking a flight which can get you there in 1h 34m. The ticket price range depends on the travel mode: a train costs an average of €119, and a flight costs an average of €295.
Distance: 328 miles (528 km)
Compare train with
Most popular Train | Flight |
|---|---|
€119 Average price Cheapest | €311 Average price |
12h 33m Average total duration 12h 3m Onboard + 30m Additional time* | 4h 34m Average total duration Fastest 1h 34m Onboard + 3h 0m Additional time* |
Direct Options | Direct Options |
Compare prices and tickets South Shore, KY to Chicago, IL by train or flight
Compare train and flight prices over the next three weeks. See the best deals at a glance, find the lowest fares, and choose the option that fits your budget.
Nov 28
Nov 29
Nov 30
Dec 01
Dec 02
Dec 03
Dec 04
Journey information
Overview: Train from South Shore, KY to Chicago, IL
Trains from South Shore, KY to Chicago, IL run on average 1 times per day, taking around 12h 3m. Cheap train tickets for this journey start at $147 (€119) if you book in advance.
There are 1 trains per day. The earliest train runs at 17:55, the last at 22:57. The fastest train covers the 328 miles (528 km) distance in 11h 3m.
Distance 328 miles (528 km) |
Average train duration 12h 3m |
Cheapest ticket price $147 (€119) |
Trains per day 1 |
Direct trains 1 |
Fastest train 11h 3m |
First train 17:55 |
Last train 22:57 |
Train companies: Amtrak from South Shore, KY to Chicago, IL trainsAmtrak trains will get you between South Shore, KY and Chicago, IL from $147 (€119). With over 1000 travel companies on Omio, you can find the best train times and tickets for your trip.
Amtrak
FAQs: Trains from South Shore, KY to Chicago, IL
Find answers to the most common questions about traveling from South Shore, KY to Chicago, IL by train. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest train, the cheapest option, or tips for making the most of your visit at Chicago, IL, this guide helps you travel smarter and with confidence.

popular train stations
Popular train stations from South Shore, KY to Chicago, IL
- 5:00 AM - 12:00 AM Monday - Sunday
- Free
- The car park is open 7 days a week from 5:00 a.m. to 12:00 a.m. Departures can be made outside of opening hours. Access via Canal Street.
- The Chicago Firehouse Restaurant
- Lou Mitchell's
- Outside the main entrance.
- Elevators, ramps, restrooms.
- $1
- The Kimpton Gray Hotel
- JW Marriott Chicago
- W Chicago - City Center
- Located in the main hall
- Located in the main hall
- Avis
- Budget
- Enterprise
- Located in the main hall
- Free
- Hall 1: main entrance, Amtrak services
- Hall 2: Metra services
- Hall 3: food court and retail shops
- Bus: Several lines available
- CTA: Blue Line, Pink Line
More options for your journey from South Shore, KY to Chicago, IL
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