Cheap train tickets from Freeport to Chicago
Find and compare the best ground travel options in one place.
Trip Summary
There are usually 2 daily train trips available from Freeport to Chicago. Travelling by train from Freeport to Chicago usually takes 1 day, 6 hours and 29 minutes, but the fastest Amtrak train can make the trip in 1 day, 5 hours and 29 minutes.
- Distance
- 896 mi (1442 km)
- Fastest train
- 29h 29m
- Lowest price
- £159.75
- Trains per day
- 2
- Most frequent service
- Amtrak
- Train lines
- 1
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Freeport to Chicago Train Timetable

There are several train options that can take you from Freeport to Chicago:
See more detailsPrice trends for trains from Freeport to Chicago
Prices as travel date approaches
Which train should you take from Freeport to Chicago?
Amtrak is the one and only train line which connects Freeport to Chicago. The schedule is relatively limited as the train only runs twice a day.
| Train | Daily Trips | Avg. Time | Avg. Price |
|---|---|---|---|
| Amtrak | 2 | 30h 29m | £163.83 |
Amtrak is the largest passenger railway 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 toilet, free WiFi and power sockets at every seat. There are also snack bars where you can purchase drinks or food during your journey. On average, there are 2 Amtrak trains from Freeport to Chicago every day, as well as 2 trips at the weekends, with prices starting from £159.75.










Frequently asked questions about travelling by train from Freeport to Chicago
Trains leave the station in Freeport twice a day, so there are a couple of options depending on your preferred travel time. However, there are no direct trains. This means that you will need to disembark from your original train and board a connecting train at some point during your journey. You will need to remember to bring your hand luggage with you when you change trains. Depending on the carrier's policy, you may also be responsible for transferring your own checked baggage.
Trains per day
2
Direct trains
0
The distance between Freeport and Chicago is approximately 896 miles. The average train journey between these two cities takes 1 day, 6 hours and 29 minutes, although the absolute fastest you could get there is 1 day, 5 hours and 29 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 patchy signal, or is among the few without Wi-Fi, we also recommend downloading TV shows and films to your mobile device in advance of your trip. That way the ride will fly by whatever the Wi-Fi situation.
Distance (mi)
896
Distance (km)
1442
The earliest train departs Freeport at 4:43 while the last train of the day leaves at 6:43. To see all scheduled departure times, use the search function on this page to get the full timetable for your specific travel dates.
First train
4:43am
Last train
6:43am
Trains from Freeport to Chicago are the most crowded on Saturday. Tickets also tend to be more expensive then. If you are looking for a great deal on your train tickets or just want extra room to stretch out, consider travelling on Saturday instead, as it tends to be the least crowded day of the week.
Busiest
Saturday
Least crowded
Saturday
City Information
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 holiday 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 neighbourhoods like Andersonville and Wicker Park. And don't miss the chance to laugh until you cry at The Second City comedy theatre, famous for launching the careers of comedians like Tina Fey and Stephen Colbert.
Chicago is one of the biggest transport 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 coach and train stations throughout the city, getting to the Windy City is a breeze.
Station Information
Where is the train station in Freeport?
Main departure station: 23 Depot Rd
There is one train station in Freeport.
All train stations in Freeport:
- 23 Depot Rd
Where is the train station in Chicago?
Main arrival station: Union Station


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 coach 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:
- Union Station

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