The cheapest and fastest trains from Chesterfield, MO to Chicago, IL
Cheapest price
$52
Average price
$52
Fastest journey
5 h 3 m
Average duration
5 h 3 m
Trains per day
1
Distance
433 km
The best way to find a cheap train ticket from Chesterfield, MO 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 Chesterfield, MO to Chicago, IL will cost around $52 if you buy it on the day, but the cheapest tickets can be found for only $52.
Of the 1 trains that leave Chesterfield, MO for Chicago, IL on Mon, Nov 24, 1 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Mon, Nov 24 the direct trains cover the 433 km distance in an average of 5 h 3 m but if you time it right, some trains will get you there in just 5 h 3 m .
On Mon, Nov 24 the slowest trains will take 5 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 bus, train, and flight for Chesterfield, MO to Chicago, IL
Omio recommends booking the flight as it is the most popular option from Chesterfield, MO to Chicago, IL among Omio's users. If you are prioritising price take the bus with prices starting from €95. For those with little time consider booking a flight which can get you there in 1h 22m. The ticket price range depends on the travel mode: a bus costs an average of €95, and a flight costs an average of €326.
Distance: 269 miles (433 km)
Compare flight with
Most popular Flight | Bus |
|---|---|
€326 Average price | €95 Average price Cheapest |
4h 22m Average total duration Fastest 1h 22m Onboard + 3h 0m Additional time* | 12h 40m Average total duration 12h 10m Onboard + 30m Additional time* |
Direct Options | Direct Options |
Compare prices and tickets Chesterfield, MO to Chicago, IL by bus, train, or flight
Compare bus, 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 24
Nov 25
Nov 26
Nov 27
Nov 28
Nov 29
Nov 30
Journey information
Overview: Train from Chesterfield, MO to Chicago, IL
Take a train from Chesterfield, MO to Chicago, IL and enjoy the approximately 269 miles (433 km) long journey. Find schedules and pricing options for a convenient and affordable trip.
There are 7 trains per day.
Distance 269 miles (433 km) |
Average train duration 5h 26m |
Trains per day 11 |
Direct trains 7 |
Train companies: Amtrak from Chesterfield, MO to Chicago, IL trainsAmtrak trains will get you between Chesterfield, MO and Chicago, IL from $117 (€95). With over 1000 travel companies on Omio, you can find the best train times and tickets for your trip.
Amtrak
FAQs: Trains from Chesterfield, MO to Chicago, IL
Find answers to the most common questions about traveling from Chesterfield, MO 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 Chesterfield, MO 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 Chesterfield, MO to Chicago, IL
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