The 5 Most Scenic Train Rides You Can Take from Chicago
From a bucket-list journey across the Rockies to a charming local day trip, this is your guide to the most incredible scenic train adventures starting right here in Chicago.
December 13, 2025 •
4 min read
There's a certain romance to train travel—the gentle rock of the car, the stunning landscapes unfolding outside your window, and the feeling of journeying to somewhere new without the stress of airports or traffic.
As the nation's railway hub, Chicago is the starting point for some of the most beautiful train rides in the country.
From epic cross-country adventures to charming local day trips, here are the scenic train rides that will make you fall in love with the journey all over again.
## 1. The California Zephyr to San Francisco (The Epic One)
*Photo By @railfandepot*
Let's start with the headliner.
Hailed by many as the most beautiful train ride in North America, this 52-hour Amtrak journey is a true bucket-list adventure.
After leaving Chicago, you'll cross the plains of Nebraska, climb through the heart of the Rocky Mountains in Colorado, snake through the canyons of Utah, and traverse the Sierra Nevadas before descending to the California coast.
It's a breathtaking, epic voyage that showcases the country's grandeur, and it all starts at Union Station.
For the best views, make sure to spend time in the Sightseer Lounge car with its panoramic windows.
## 2. The South Shore Line to the Indiana Dunes (The "Wine Train" Experience)

*Photo by @indianadunesnps on Instagram*
For a perfect day trip that feels a world away, hop on the South Shore Line from Millennium Station.
This unique ride takes you along the southern coast of Lake Michigan to the stunning landscapes of Indiana Dunes National Park, where you can hike and enjoy the beaches.
But the real secret is the **Dune Buggy Wine Trail Tour**.
They can pick you up from a nearby station and take you on a guided tour to multiple local wineries and cideries.
It's Chicago's answer to a wine train, and it's a fantastic and surprisingly easy getaway.
## 3. The Metra UP-North Line to Kenosha (The Lakefront Cruise)
This is a local secret for a cheap and beautiful scenic ride.
The Metra Union Pacific-North line, departing from Ogilvie Transportation Center, hugs the Lake Michigan shoreline as it travels through the stunning, historic suburbs of the North Shore like Evanston, Glencoe, and Lake Forest.
The views of the lake are spectacular. For a fun day trip, take it all the way to the last stop in Kenosha, Wisconsin.
You can explore the lakeside parks, visit a few local breweries, and enjoy the charming downtown before heading back to the city.
## 4. The Hiawatha to Milwaukee (The Quick City Escape)
Sometimes you just need a quick change of scenery.
The Amtrak Hiawatha Service is a fast (just 90 minutes) and incredibly scenic trip that takes you through beautiful Illinois and Wisconsin prairies on your way to Milwaukee.
It's the perfect way to have a "two-city" weekend without the hassle of driving.
You can explore the Historic Third Ward, visit the iconic Milwaukee Art Museum, and enjoy the city's famous brewery scene, all just a comfortable train ride away.
## 5. The Pere Marquette to Grand Rapids (The Michigan Getaway)
This Amtrak route offers a beautiful journey east into the heart of Michigan.
The ride is especially gorgeous in the fall when the leaves are changing, taking you through charming small towns and lush forests.
When you arrive in Grand Rapids, you're in the center of one of America's best beer cities ("Beer City USA") and just a short drive from the beautiful sandy beaches of the Lake Michigan coastline. It's an underrated and scenic trip that's perfect for a long weekend.
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