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Trip Summary
You can pick from 4 daily train trips between Stamford and Chicago. The average train journey from Stamford to Chicago takes 24 hours and 56 minutes, but some Amtrak train trips are as short as 22 hours and 17 minutes.
| Distance | 731 mi (1176 km) |
| Fastest train | 22h 17m |
| Lowest price | $138.03 |
| Most frequent service | Amtrak |
| Train lines | 1 |
What is the price of a train ticket from Stamford to Chicago?
In the last 30 days, the average cost of a train ticket from Stamford to Chicago was $211.19. Tickets for this route are somewhat expensive, given the distance between Stamford and Chicago. You have the best chances of scoring the cheapest ticket to Chicago if you book your train tickets at least 20 days in advance. Waiting to purchase until the day of your trip could end up costing you an extra $273.76.
Monthly average prices
Ticket prices for the train from Stamford to Chicago often fluctuate based on the time of year. For the best prices on this route, book in February when the average ticket price is only $222,
If you're thinking of traveling from Stamford to Chicago during August, keep in mind that train ticket prices may be higher than usual, with an average price of $431 during this time of year. The best way to score a cheap deal, even in August, is to book your trip well in advance.
Prices as travel date approaches
If you want to score the best deal, you should plan to book your train trip online on Wanderu at least 20 days ahead of time. If you do that, your train ticket to Chicago from Stamford will be about C$273.76 cheaper compared to what you would pay if you book at the last minute.
Which train should you take from Stamford to Chicago?
Amtrak is the one and only train line which connects Stamford to Chicago. However, there are 4 trains per day to choose from.
| Train | Daily Trips | Avg. Time | Avg. Price |
|---|---|---|---|
| Amtrak | 4 | 1d 0h 56m | $345.55 |
Amtrak is the largest passenger railroad service in America, offering daily intercity trains to hundreds of destinations across the contiguous United States, as well as several cities in Canada. Every Amtrak train comes equipped with comfortable seats with extra legroom, as well as several four-seat areas with tables in the middle. In addition, each car has a freshly cleaned restroom, free WiFi and power outlets at every seat. There are also snack bars where you can purchase drinks or food during your journey. On average, there are 4 Amtrak trains from Stamford to Chicago every day, as well as 2 trips on the weekends, with prices starting from $138.
Frequently Asked Questions
The distance between Stamford and Chicago is approximately 731 miles, or 1176 kilometers. The average train journey between these two cities takes 24 hours and 56 minutes, although the absolute fastest you could get there is 22 hours and 17 minutes.
Looking for ways to pass the time? Most trains are equipped with Wi-Fi, which means you can stream music, browse social media or get some work done during your ride. That said, in case your train has a spotty signal, or is among the few without Wi-Fi, we also recommend downloading TV shows and movies to your mobile device in advance of your trip. That way the ride will fly by whatever the Wi-Fi situation.
On a weekly basis, the greatest number of passengers tend to travel by trains from Stamford to Chicago on Wednesday. Tickets for Wednesday tend to also be the most expensive. For savvy travelers looking for cheaper priced tickets search for travel departing on Monday. Monday also tend to have less passengers which may make boarding faster and let you snag your perfect seat.
The earliest train departs Stamford at 8:00am while the last train of the day leaves at 12:00pm. To see all scheduled departure times, use the search function on this page to get the full schedule for your specific travel dates.
There are 4 scheduled trains on most days. Unfortunately, none of them are direct connections, so you will need to disembark from your original train and board a connecting train during your journey. Don't forget to bring your carry-on luggage when you switch trains. In some instances, you may also be responsible for transferring your own checked baggage.
You can also take a train for your return trip from Chicago to Stamford.
City Information
Stamford
Stamford is one of the most populous cities in the state of Connecticut, and many residents commute into New York City, about 30 miles southwest. You can even see NYC from Greenwich Point Park, a scenic spot on Long Island Sound. But don't get too distracted by the Big Apple; there is plenty to enjoy in Stamford itself!
The Stamford Museum and Nature Center is a 118-acre museum that includes a working farm, an art gallery, outdoor trails, a planetarium, an otter pond, and endless activities for visitors of all ages. Visitors of legal ages will also love the many clubs, bars, and breweries in downtown Stamford. Some popular spots for drinks and dinner are Olio, Brasitas, and ZAZA Italian Gastrobar.
Stamford is a major transportation hub for travelers in the region. The Stamford train station is the second-busiest in the Metro-North system, after only Grand Central Station. Commuter rails connect Stamford to New York City and New Haven, and Amtrak trains provide service to Boston, Washington, and beyond. Or, OurBus and Greyhound offer intercity bus tickets as a more affordable alternative to trains. Stamford benefits from many airports in the region, but the closest international airport is LaGuardia in Queens.
Chicago
Known for its innovative architecture, cultural contributions to jazz and house music, and of course that irresistible deep-dish pizza, the many sights and experiences in Chicago make it one of the best urban vacation destinations for millennials and a top destination in Illinois.
You can't beat the views of the city and Lake Michigan from the SkyDeck in the Willis Tower; at over 1,300 feet, this is the highest observation deck in the U.S. Snap that classic selfie with the Bean in Millennium Park, then wander the many museums in nearby Grant Park. Navy Pier is a popular tourist hotspot for its parks, restaurants, and attractions right on Lake Michigan, and baseball fans will find paradise in Wrigleyville, home to the Chicago Cubs' Wrigley Field and sports bars galore.
Chicago's enormous parks offer plentiful opportunities for outdoor activities in gorgeous urban settings. Many companies offer kayak rentals or boat tours on the Chicago River, with special tours running on Saint Patrick's Day, when the entire river is dyed green. When you’re ready to buy some souvenirs from your epic trip, hit the big brand stores on the Magnificent Mile, or shop local in neighborhoods like Andersonville and Wicker Park. And don't miss the chance to laugh until you cry at The Second City comedy theater, famous for launching the careers of comedians like Tina Fey and Stephen Colbert.
Chicago is one of the biggest transportation hubs in the Midwest, and provides easy access to nearby destinations ideal for day trips, as well as international travel from two airports. Thanks to plenty of bus and train stations throughout the city, getting to the Windy City is a breeze.
Station Information
Where is the train station in Stamford?
Main departure station: Amtrak/Metro North Station
There is one train station in Stamford.
All train stations in Stamford:
Amtrak/Metro North Station
Where is the train station in Chicago?
Image credit: Jeramey Jannene
Link to image attribution
Main arrival station: Chicago (Union Station), Illinois
The historic Chicago Union Station is the United States' third busiest train station and a hub for 15 Amtrak train lines with destinations throughout the country. The station also serves bus carriers like Greyhound, Indian Trails and Jefferson Lines, and offers connections to Metra commuter lines. Union Station is also just a quick walk to the nearest Chicago L lines. The current station was built in 1925, to replace the original one dating back to 1881, and today wows visitors with its impressive facade, massive columns, and opulent Great Hall. Located right in downtown and adjacent to the Chicago Loop, Union Station is equipped with many services and amenities, including phone charging stations, shops, and various food and drink options.
Train stations in Chicago:
Chicago (Union Station), Illinois
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