Next train departures
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link |
|---|---|---|---|---|---|---|---|---|
 | Train | Union Station | Chicago (Union Station), IL | Cheapest | ||||
| Train | Union Station | Chicago (Union Station), IL | Fastest | ||||
| Train | State Street Station | Chicago (Union Station), IL | No tags | ||||
NextGen Acela + Amtrak | Train | Union Station | Chicago (Union Station), IL | No tags | ||||
| Train | Union Station | Chicago (Union Station), IL | No tags |
Last refresh of the prices: Yesterday at 5:22 PM EST.
Compare 2 ways to go from New Haven to Chicago
Among the sustainable travel choices, the bus stands out as a good way to reach Chicago. The journey takes about 1 day, 4 hours 55 minutes, and with fares starting at just $99, it presents an excellent value for a comfortable ride.
Train companies
Based on 5600 reviews, the company was rated 4.1 stars on Busbud. Travellers were especially satisfied with the seats and the ticket access but often complained with the WiFi. Amtrak ticket prices on this trip start at $218
Frequently asked questions about travelling from New Haven, CT to Chicago by train
How much does a cheap train ticket from New Haven to Chicago cost?
The average train ticket price from New Haven to Chicago is $435. The best way to find cheap train tickets from New Haven to Chicago is to book your tickets as early as possible. Prices tend to rise as your travel date approaches, so book in advance to secure the best prices!
How long is the trip from New Haven to Chicago?
A train trip between New Haven and Chicago is around 1d , although the fastest train will take about 23h 6m. This is the time it takes to travel the 1226 km that separates the two cities.
How many daily trains are there between New Haven and Chicago?
The number of trains from New Haven to Chicago can differ depending on the day of the week. On average, there are 5. Some trains are direct while others include transferring trains. Simplify your train trip from New Haven to Chicago by comparing and selecting the train that fits your travel style and budget on Busbud.
Which train companies travel from New Haven to Chicago?
When taking the train from New Haven to Chicago, you can travel comfortably and safely with Amtrak.
Find cheapest prices for trains
Price is for a one-way ticket for one passenger and based on past searches.
The cheapest trip from New Haven, CT to Chicago was searched and found on Nov 22, 2025 with a price of $275To save money and be sure you have the best seat, it's a good idea to buy your train tickets from New Haven, CT to Chicago, as early as possible.
You can expect to pay from $275 to $1,731 for a train ticket from New Haven, CT to Chicago based on the last 2 days. You can expect to find the cheapest price for the trip at $278 which is on 2025-11-27.
