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 between San Francisco and Chicago (The Epic One)
If you’re going to leave the greatest city on earth, you might as well do it with some drama.
This isn’t a quick jaunt to the suburbs; this is the big one.
The California Zephyr is widely considered the crown jewel of American rail travel, and lucky for us, it starts right here at the Great Hall in Union Station.
Forget flying over “flyover country.”
This 51-hour haul forces you to stare it in the face until it transforms into something entirely different. You roll out of the Chicago concrete, pushing through the flat expanse of Illinois and Iowa cornfields. It’s quiet. It’s rhythmic. But don’t get too comfortable.
By the next morning, the scenery shifts violently. You aren’t in the Midwest anymore.
The tracks start climbing, dragging you up into the Colorado Rockies. You’ll pass through the Moffat Tunnel—which cuts right through the Continental Divide—and suddenly, you’re looking down at the world.
The views from the Sightseer Lounge (that’s the car with the floor-to-ceiling windows) are ridiculous. We’re talking the jagged red rocks of the Utah desert, the snowy peaks of the Sierra Nevadas, and the infamous Donner Pass.
It’s a front-row seat to the wildest geography the continent has to offer. By the time you pull into Emeryville—just a bridge crossing away from San Francisco—you’ll feel like you actually earned the West Coast.
Pro Tip: Grab a sleeper car if your wallet allows. Waking up horizontally while the train snakes through a canyon is a flex you won’t forget.
2. The South Shore Line to the Indiana Dunes (The “Wine Train” Experience)
Most people assume you need a flight and a rental car to hit a National Park. In Chicago, you just need a Ventra card and twenty bucks.
This isn’t your standard CTA commute; the South Shore Line (departing from the underground slickness of Millennium Station, not Union) is the weirdest, coolest transition you’ll see out a train window.
Locals joke about this being our “Wine Train” because it’s the easiest way to pull off a Napa-style day trip on a rust-belt budget.
The ride itself is a masterclass in contrast. You slide past the ghostly, industrial skeletons of Gary and the active blast furnaces of “The Region”—fire, smoke, and steel. It’s gritty, honest, and oddly mesmerizing.
But then, you hop off at the Dune Park station, and the script flips. You’re suddenly standing on the edge of the Indiana Dunes National Park. We’re talking 15,000 acres of massive sand hills and forest trails that hug the southern tip of the lake.
For the full experience, skip the hike for an hour and hit up the wineries and taprooms in nearby Chesterton (a quick Uber or the “Dunes Kankakee Trail” walk from the station).
You get the beach, the bizarre industrial skyline, and a glass of local vino without worrying about traffic on the Skyway. It’s the perfect unpretentious escape.
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3. The Metra UP-North to Kenosha (The $10 Lakefront Tour)
This is the ultimate local loophole. Most people think Metra is just for sad commuters in suits, but the Union Pacific-North line out of Ogilvie is secretly the best scenic deal in the city.
For the price of a sandwich, this double-decker crawls up the spine of the North Shore.
You aren’t staring at highway barriers here; you’re looking into the backyards of the most expensive real estate in Illinois—Evanston, Glencoe, Lake Forest. It hugs the lake tightly enough that you get actual water views between the trees and the mansions.
Take it all the way to the end of the line. You cross the Cheddar Curtain into Kenosha, Wisconsin, where the vibe instantly shifts. The station drops you right near the harbor.
You can hop on an electric streetcar, grab a Spotted Cow at a dive bar, and raid the Tenuta’s Deli for Italian supplies before riding back. It’s a low-stakes, high-reward Saturday.
4. The Hiawatha to Milwaukee (The 90-Minute Escape Hatch)
Sometimes the best scenery is watching Chicago disappear in the rearview mirror when you need a break.
The Hiawatha is our collective escape hatch. It’s fast, frequent, and dumps you into the “Good Land” in less time than it takes to drive to O’Hare in rush hour.
Is the ride itself a nature documentary?
No. It’s an industrial tour of the Rust Belt corridor, but there’s a gritty charm to it. You slide through the guts of the Midwest until the scenery opens up into Wisconsin fields.
The payoff is the arrival. You land at Milwaukee’s sleek downtown station, and you’re immediately within striking distance of the Third Ward and the lakefront Art Museum (the one that looks like a bird taking off). It’s the easiest way to pull a “two-city weekend” without touching a steering wheel. Drink the beer, eat the curds, catch the 9 p.m. train back, and wake up in your own bed.
5. The Pere Marquette to Grand Rapids (The Fall Foliage Fix)
If the Zephyr is about mountains and the South Shore is about grit, the Pere Marquette is about trees. Lots of them. This route hooks around the bottom of Lake Michigan and heads north into the Mitten.
While this ride is decent year-round, it becomes essential in October. When the seasons turn, this train cuts through a tunnel of red and gold leaves that you just don’t get in the flatlands of Illinois. It feels like you’re actually away.
It drops you in Grand Rapids, a city that takes beer more seriously than arguably anywhere else in the country.
You’re close enough to the Michigan dunes for a day trip, but honestly, staying in town to hit the breweries and the massive antique markets is the move. It’s the perfect antidote to Chicago burnout
