Chicago is one of the best cities for train travel. Sixteen Amtrak routes arrive and depart from Chicago Union Station, so there are many options for day, weekend or multiple-day getaways. Here are some of the best trip options listed in order of travel time so you can start planning your rail adventure. Destinations were selected based on convenient train departure times and unique things to see and do.
For a day or overnight trip, travel to Milwaukee on the Hiawatha Amtrak route. There are several museums and a zoo to explore, including the Harley-Davidson Museum, which is in walking distance of the Amtrak station. You can also go to a baseball game at the American Family Field or choose from several brewery tours.
Trains depart Chicago about every two hours, with the first train arriving in Milwaukee before 8 a.m. The last train back to Chicago departs around 7:30 p.m., so a day trip is easily doable. Travel time is about 1.5 hours.
St. Joseph/Benton Harbor
Escape the city and experience Lake Michigan from the charming towns of St. Joseph and Benton Harbor via the Pere Marquettte Amtrak route. In addition to beaches and parks, explore the Sarett Nature Center, Silver Beach Carousel and wineries. This trip from Chicago is only two hours and one-way tickets are about $20 (price as of June 2021). Plan to stay at least one night in Michigan as there is only one train each day, with a departure from Chicago at 6:30 p.m.
Book a trip on the Texas Eagle or Lincoln Service to visit Springfield, the Illinois capital. Travel time is about 3 hours and 20 minutes, with your choice of a morning or afternoon departure from Chicago. Major attractions here include the Abraham Lincoln Presidential Library and Museum, Lincoln Home National Historic Site, Illinois State Museum and various other historic homes and parks.
For the return trip, there are daily morning and evening trains. If you plan to do a day trip, you’ll have about six hours to explore if you choose the morning departure from Chicago and evening departure from Springfield.
A great destination for kids, the Wisconsin Dells is full of water parks, theme parks, wildlife parks and outdoor activities. It’s approximately a four-hour train ride from Chicago on the Empire Builder, with an arrival around dinnertime. Plan to stay two nights in order to have a full day to visit the local attractions. As a bonus, the Empire Builder has a sightseer lounge for panoramic views of the scenery.
About 5.5 hours away from Chicago by train, St. Louis is known for the Gateway Arch, but there are many other things to see and do. Some of the top attractions include the Missouri Botanical Garden, St. Louis Zoo, St. Louis Art Museum, Mississippi River and Busch Stadium. There is a morning departure from Chicago on the Lincoln Service train and afternoon departure on the Texas Eagle. For the return travel, you can choose between a morning or evening departure time. If you make this a true day trip, you’ll have five hours in St. Louis (arrival around 3 p.m. and departure around 8 p.m.).
Visit the majestic Niagara Falls with a getaway on Amtrak’s Lake Shore Limited route. This is an overnight trip with a morning arrival in Buffalo, New York. Roomettes and bedrooms are available for a more comfortable and private experience on the train. Travel time is 10 hours, and you’ll be sleeping most of that time.
On the return trip to Chicago, the Lake Shore Limited departs Buffalo around midnight, which means you can spend the day sightseeing and get back on the train same day instead of staying at a hotel.
You’ll need to rent a car or use a taxi or rideshare service to reach downtown Buffalo and the Niagara Falls area — both have hotels if you plan to stay overnight. An Enterprise rental car office is near the Amtrak station. Call ahead to see if they can pick you up. The falls are about a 40-minute drive away from the train station and 30 minutes from Enterprise.
The Greenbrier Resort
Travel through the beautiful New River Gorge on the Cardinal route to reach The Greenbrier, a 1778 resort with casino. The Cardinal only operates three days each week, so you will need to stay more than one night, but there are plenty of activities to keep you busy. In addition to the casino, there is a spa, golf course, swimming pools, bike rentals, bowling alley, fishing, aerial adventure course and more. Travel time is about 17 hours from Chicago, and the White Sulphur Springs Amtrak Station is conveniently next to the resort, so you don’t have to rent a car.
Washington D.C. is about 17 hours away from Chicago via the Capitol Limited route. The train departs Chicago around dinnertime and arrives at D.C. Union Station in early afternoon. At the station you can transfer to WMATA subway trains for easy access to free museums, monuments and hotels. Taxi and rideshare cars are also options for getting around. For the return trip to Chicago, there is a train that departs daily around 4 p.m. Be sure to make arrangements to stay in the nation’s capital at least one night.
New York City
Be a part of the city that never sleeps with trip to New York City. Travel time is between 19 and 20 hours on the Lake Shore Limited Amtrak route, with an arrival at the new Penn Station train hall around 7 p.m. Penn Station has connections to the MTA subway and you can easily walk to the Empire State Building and Times Square. If you plan to see a Broadway Show, you’ll need to stay two nights in the city and use your first night to get settled at your hotel and see any attractions that aren’t at a scheduled time (in case there are train delays).
Plan a trip to New Orleans for amazing food, music and culture. The City of New Orleans train departs Chicago in the evening and arrives 20 hours later in the afternoon. The return train departs each day at 1:45 p.m., so you could stay one night in New Orleans and have time to see some of the sights. Attractions to check out include the National World War II Museum, Garden District, French Quarter and historic cemeteries. There are also boat tours and streetcars for sightseeing.
Eat lobster, drink local craft beer and relive American Revolution history in Boston. The Freedom Trail is a must-do. Travel time is 21-22 hours to and from Boston’s South Station on the Lake Shore Limited route, with an evening departure from Chicago and evening arrival in Boston. You can also book your Amtrak ticket to the Back Bay Station, which is closer to Fenway Park and Copley Place shopping mall.
September and October are great months to visit, along with the summer months. Plan to stay two nights in the city, otherwise, you’ll basically only have one morning to see the sights before the daily early afternoon train back to Chicago.
The California Zephyr is arguably the most scenic Amtrak route, especially the journey through the Rocky Mountains along the Colorado River (pictured above). There are multiple Amtrak stations in the Rockies with lodging and activities so you can enjoy time there before returning to Chicago. If you love skiing, book your Amtrak ticket to Fraser/Winter Park (21-hour trip) and hit the slopes at the popular Winter Park Resort. Glenwood Springs (25 hours from Chicago), is another great option with hotels and a hot springs pool in walking distance of the Amtrak station. There are also hiking trails, whitewater rafting, an amusement park and the Frontier Historical Museum to explore.
When the weather gets cold in Chicago, head to Texas on the Texas Eagle to explore Dallas or Austin. Dallas is 22 hours away from Chicago by train and Austin is 28. Both have surprisingly walkable areas near the Amtrak stations, light rail transit and rental car options.
In Dallas, the John F. Kennedy Memorial Plaza, the site of his assassination and the Sixth Floor Museum are all in walking distance of the Dallas Amtrak Station. There are also many other museums and an aquarium nearby, or rent a car to reach the George W. Bush Presidential Library and the Dallas Arboretum and Botanical Garden.
For a vacation full of music, nightlife and outdoor recreation, travel to Austin. There are many parks along the Colorado River to explore, boat rentals and tours, kayaking, paddleboarding, festivals, and live entertainment on 6th Street.
Albuquerque is 26 hours away from Chicago on the Southwest Chief. It’s New Mexico’s largest city, plus you’ll travel through mountains on the way there. Top attractions include Sandia Peak Tramway for gorgeous panoramic views, Indian Pueblo Cultural Center, National Museum of Nuclear Science and the Petroglyph National Monument. There’s also plenty of things to check out near the Amtrak station, including a zoo, botanic garden, Old Town Albuquerque, and trails along the Rio Grande River. Consider planning your trip around the Albuquerque International Balloon Fiesta, which is a major event in the fall.
Glacier National Park
Take Amtrak to Glacier National Park on the Empire Builder to see stunning landscapes and relax in a historic inn. There are four train stations near the park to choose from, each with unique lodging options. East Glacier Park is the first stop, about 30 hours away from Chicago, and you can walk to the Glacier Park Lodge from the station. Next is Essex Station, which is next to the historic Izaak Walton Inn. West Glacier Station is the third station near the park, with the West Glacier Village, the 1910 Belton Chalet and other lodges in walking distance. Or get off the train in Whitefish if you want to rent a car or stay in an area near restaurants.
Travel to Los Angeles for a 43-hour, two-night trip on the entire length of the Southwest Chief Amtrak route. You’ll travel though mountains and deserts and arrive at the beautiful Los Angeles Union Station in the morning. There’s plenty to see and do in the city, including the Getty Center, Griffith Observatory, Hollywood Sign, Santa Monica Pier, theme parks, tours, shopping and beaches. If you don’t want to take Amtrak back to Chicago, there are plenty of direct flights to choose from.
Portland and Seattle
Last, but not least, is the full long-distance trip on the Empire Builder. You have the choice to travel from Chicago to either Portland or Seattle. Both options offer amazing scenery, with views of the Columbia River Gorge on the Portland route, or travel along Puget Sound and multiple rivers on the Seattle segment. You’ll also see the Rocky Mountains in Montana if you book your trip around the summer solstice. Total travel time is 46 hours, with two nights on the train. You can easily get a flight back to Chicago in Portland or Seattle to shorten the return trip.