Next departures for New Haven to Chicago on December 1
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Train
State Street Station
Chicago (Union Station), IL
Cheapest
Train
Union Station
Chicago (Union Station), IL
Fastest
Train
State Street Station
Chicago (Union Station), IL
No tags
Amtrak Acela + Amtrak
Train
Union Station
Chicago (Union Station), IL
No tags
Train
State Street Station
Chicago (Union Station), IL
No tags
Next departures for New Haven to Chicago on December 2
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Train
State Street Station
Chicago (Union Station), IL
Cheapest
Train
Union Station
Chicago (Union Station), IL
Fastest
Train
State Street Station
Chicago (Union Station), IL
No tags
Amtrak Acela + Amtrak
Train
Union Station
Chicago (Union Station), IL
No tags
Train
State Street Station
Chicago (Union Station), IL
No tags
Next departures for New Haven to Chicago on December 4
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Train
State Street Station
Chicago (Union Station), IL
Cheapest
Train
Union Station
Chicago (Union Station), IL
Fastest
Train
State Street Station
Chicago (Union Station), IL
No tags
Amtrak Acela + Amtrak
Train
Union Station
Chicago (Union Station), IL
No tags
Train
State Street Station
Chicago (Union Station), IL
No tags
Last refresh of the prices: Today at 2:04 AM EST.
Compare 2 ways to go from New Haven to Chicago
We recommend taking the bus
Among the sustainable travel choices, the bus stands out as the good way to reach Chicago. The journey takes about 1 day, 4 hours 55 minutes and with fares starting at just $76, it presents an excellent value for a comfortable ride.
Based on 5617 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 $151
Frequently asked questions about traveling from New Haven, CT to Chicago by train
How much does a train ticket from New Haven to Chicago cost?
The average train ticket price from New Haven to Chicago is $325. The best way to find 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 train 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 761 miles 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 have layovers. 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.
What are the best sights and things to do in Chicago?
Once in Chicago, you can explore the city. The top sights and things to do are Museum of Contemporary Art, Willis Tower (Sears Tower), Chicago Shakespeare Theater on Navy Pier, Navy Pier, Lincoln Park Zoo.
Find cheapest prices for trains
Price is for a one-way ticket for one passenger and based on past searches.
Best price found
11/28
$443
11/29
$625
Today
$545
12/01
$288
12/02
$202
12/03
$115
12/04
$207
12/05
$144
The cheapest trip from New Haven, CT to Chicago was searched and found on Dec 3, 2025 with a price of $115
To 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 $115 to $2,130 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 $115 which is on 2025-12-03.