Trains leaving Saturday
One passenger / one way
- This trip is recommended because it is: CheapestDeparture time: August 16 atDeparture city: StamfordDeparture location: Stamford StationArrival time: August 18 atDestination city: ChicagoDestination location: Chicago (Union Station), ILOperated by: Amtrak
Vehicle: TrainDuration: - This trip is recommended because it is: FastestDeparture time: August 16 atDeparture city: StamfordDeparture location: Stamford StationArrival time: August 17 atDestination city: ChicagoDestination location: Chicago (Union Station), ILOperated by: AmtrakVehicle: TrainDuration:
- Departure time: August 16 atDeparture city: StamfordDeparture location: Stamford StationArrival time: August 17 atDestination city: ChicagoDestination location: Chicago (Union Station), ILOperated by: AmtrakVehicle: TrainDuration:
- Departure time: August 16 atDeparture city: StamfordDeparture location: Stamford StationArrival time: August 17 atDestination city: ChicagoDestination location: Chicago (Union Station), ILOperated by: AmtrakVehicle: TrainDuration:
- Departure time: August 16 atDeparture city: StamfordDeparture location: Stamford StationArrival time: August 17 atDestination city: ChicagoDestination location: Chicago (Union Station), ILOperated by: AmtrakVehicle: TrainDuration:
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Compare 2 ways to go from Stamford to Chicago.
Busbud recommends taking the bus from Stamford to ChicagoAmong the sustainable travel choices, the bus stands out as the good way to reach Chicago. The journey takes about 1 day, 5 hours 45 minutes and with fares starting at just $152, it presents an excellent value for a comfortable ride.
Train Stamford, CT, US to Chicago: Trip Overview
Please note, this information is subject to change.
Train Companies
Based on 5390 reviews, the company was rated 4.1 stars on Busbud. Travelers were especially satisfied with the seats and the ticket access but often complained with the wifi. Amtrak ticket prices on this trip start at $116
Stamford to Chicago Train
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Where are the popular train stations and stops in Stamford, CT, US and Chicago?
Frequently asked questions for your trip Stamford, CT, US - Chicago
Find cheapest prices for trains
Price is for a one-way ticket for one passenger and based on past searches.
The cheapest trip from Stamford, CT, US to Chicago was searched and found on Aug 13, 2025 with a price of $197To save money and be sure you have the best seat, it's a good idea to buy your train tickets from Stamford, CT, US to Chicago, as early as possible.
You can expect to pay from $197 to $1,164 for a train ticket from Stamford, CT, US to Chicago based on the last 2 days. You can expect to find the cheapest price for the trip at $225 which is on 2025-08-16.
About Train Travel
Train Travel Tips
Taking the fastest trains allows you to travel at speeds greater than 300 km/h. Taking a trip from Stamford to Chicago is not only much quicker but more comfortable too! You can usually travel directly to the city centre and save time while you're at it.
No matter if you plan to take a regional or high-speed train to Chicago, the planet will thank you. You’ll help to protect the beautiful landscapes that will unfold before your very eyes.
By choosing the train between Stamford and Chicago, you emit up to 30 times less CO2 than for the same journey made by plane or car!
Make a music playlist for your train ride from Stamford to Chicago, and enjoy the scenery to tunes from your own personal soundtrack.
Did you know?
You can find the straightest railway in the world in Australia. This railway line is 478 kilometres long and is also considered the longest and straightest railway line in the world.
You can find dogs as passengers on the trains of Moscow, where there is a large number of stray dogs. Over time, the dogs have learned the inner workings of the rail system and it is not uncommon to find one traveling between the city and the suburbs.
The first high-speed train line was inaugurated in 1964, in Japan, to connect Tokyo with Osaka. It was during the Olympics that the first passengers traveled aboard the Shinkansen at a speed of 210 km / h.
Top Traveled Train Routes
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Popular Trains Connecting Stamford
Trains Leaving from Stamford
Popular Trains Connecting Chicago
Trains Going to Chicago
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