- Must visit
Art Institute Of Chicago
One of the world’s leading art museums, famous for Impressionist masterpieces, American art, and major special exhibitions.
We are not able to find a train between these two places.
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Omio recommends booking the train as it is the most popular option from Chesterfield, MO to Chicago, IL among Omio's users. If you are prioritising price take the train with prices starting from $42. For those with little time consider booking a flight which can get you there in 1h 26m. The ticket price range depends on the travel mode: a train costs an average of $42, and a flight costs an average of $408.
Distance: 269 miles (433 km)
Most popular Train | Flight | Bus | Driving |
|---|---|---|---|
$42 Average price Cheapest | $408 Average price | $56 Average price | $64 Average price (fuel + tolls) |
6h 4m Average total duration 5h 34m Onboard + 30m Additional time* | 4h 26m Average total duration Fastest 1h 26m Onboard + 3h 0m Additional time* | 6h 45m Average total duration 6h 15m Onboard + 30m Additional time* | 4h 30m Average total duration (door-to-door) |
Direct Options | Direct Options | Direct Options | Direct Options |
This is compared to other travel options from Chesterfield, MO to Chicago, IL:
A train is $14 (€11) less than a bus for this route with tickets for a bus from Chesterfield, MO to Chicago, IL costing on average $56 (€46).
A train is $365 (€300) less than a flight for this route with tickets for a flight from Chesterfield, MO to Chicago, IL costing on average $408 (€335).
Other travel options to Chicago, IL take longer:
Train takes on average 5h 34m.
Bus takes on average 6h 15m.
Tickets start at around {cheapestPrice} compared to roughly {drivingPriceInCents} in fuel and tolls — a saving of about {savingsAmount}. The journey takes {durationInMinutes} versus {drivingDurationInMinutes} by car, so you'll arrive a bit later, but you can work, read, or sleep along the way rather than spending the time behind the wheel. You'll also save the hassle of parking at the other end.
Direct services run with Amtrak.
Driving is worth it if you're on a tight schedule, travelling as a group, or want to stop somewhere en route.
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.
Trains from Chesterfield, MO to Chicago, IL run on average 10 times per day, taking around 5h 34m. Cheap train tickets for this journey start at $42 (€35) if you book in advance.
There are 6 trains per day. The earliest train runs at 04:30, the last at 23:00. The fastest train covers the 269 miles (433 km) distance in 4h 55m.
Distance 269 miles (433 km) |
Average train duration 5h 34m |
Cheapest ticket price $42 (€35) |
Trains per day 10 |
Direct trains 6 |
Fastest train 4h 55m |
First train 4:30 AM |
Last train 11:00 PM |
Cheapest Month Jan |
Cheapest Day Sat |
High Season Apr - Jun |
Low Season Jul - Sep |
Discover the best of Chicago — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Chicago trip today.
One of the world’s leading art museums, famous for Impressionist masterpieces, American art, and major special exhibitions.
A top natural history museum known for Sue the T. rex, ancient cultures, fossils, and broad science collections.
A large hands-on science museum with a German submarine, space exhibits, and interactive engineering displays.
Chicago’s signature downtown park, home to Cloud Gate, gardens, public art, and major seasonal events.
The city’s best-known avenue for architecture, shopping, and bustling urban energy along North Michigan Avenue.
A popular pedestrian waterfront with excellent skyline views, bridges, and easy access to boat architecture tours.
A thick, buttery crust pizza baked in a deep pan with layers of cheese, toppings, and chunky tomato sauce. It is one of Chicago’s most iconic and debated local specialties.
An all-beef hot dog on a poppy seed bun topped with yellow mustard, relish, onions, tomato, pickle spear, sport peppers, and celery salt. It is a classic local street food served without ketchup.
Thinly sliced seasoned roast beef piled onto an Italian roll, often dipped in its juices and topped with sweet peppers or giardiniera. It is a defining working-class Chicago sandwich.
Chicago’s world-famous fine-dining restaurant known for highly creative tasting menus and theatrical presentation. It offers one of the city’s most celebrated upscale dining experiences.
A beloved casual institution best known for breaded steak sandwiches and hearty Italian-American comfort food. It has a loyal local following and an old-school atmosphere.
A legendary Chicago chain celebrated for buttery-crust deep-dish pizza and a classic casual atmosphere. One of the city’s best-known places to try this signature dish.
Chicago is pricey for hotels and dining, but budget eats and public transit help keep daily costs manageable.
Tip 18-20% at restaurants; 15-20% for taxis and rideshares; USD 1-2 per drink at bars; USD 1-2 per bag for bellhops; USD 2-5 per night for housekeeping.
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.

Most Chesterfield, MO to Chicago, IL trains use the St. Louis Station to Union Station station pair. Use this guide to compare Chesterfield, MO and Chicago, IL train stations on this route, check city-centre transport, alongside checking practicalities like train station facilities and services.
Union Station is 3 km from Chicago city centre. Public transport options include:
Union Station has practical services for this route, including Wifi, Lockers, Parking, Dining, ATM, Taxis, Accessibility, WC, Hotel, Lounge, Lost and Found Office, Ticket Office, Bike Parking, Car Rental, Information Desk, and Luggage Carts.
Food options include: The Chicago Firehouse Restaurant, Lou Mitchell's
Free. ATMs are available in the train station.
Ticket office support is available at Union Station. Information desks are located in the main hall.
Luggage storage is available at Union Station. Lost and found is available at the station.
Available at Union Station: Parking, Taxis, WC.
Available at Union Station: Bike Parking, Car Rental.
Accessibility facilities are available at Union Station: Elevators, ramps, restrooms.
Nearby hotels include The Kimpton Gray Hotel, JW Marriott Chicago, W Chicago - City Center.
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