Saint Paul, Chicago, Washington D.C. by Train
By Anthony T. Eaton
Each January, as snow blankets the Midwest, Amtrak quietly releases a deal for wanderers with time and curiosity to spare: a discounted rail pass offering 10 coach segments over 30 days. My travel companion Steven and I, both longtime fans of train travel, jumped at the chance. Our plan was simple—depart from the historic Union Depot in Saint Paul and explore cities connected by rail, no car required. I mapped out two itineraries, and we chose one that would use four of our ten segments: Saint Paul to Washington, D.C., via Chicago.
We left on a Monday and Steven picked me up just before 8 a.m. for the short drive to the historic Union Depot in Lowertown Saint Paul. The Saint Paul Union Depot officially restarted Amtrak train service on May 7, 2014.
After decades of decline and disuse, the depot underwent an extensive renovation and restoration project that began in 2011. The $243 million project transformed the historic 1920s Beaux-Arts station back into a multi-modal transit hub. When Amtrak’s Empire Builder began serving Union Depot again in 2014, it marked the return of intercity passenger rail to the building for the first time since 1971.
Since then, Union Depot has served as the primary Amtrak station for the Twin Cities, replacing the more utilitarian Midway Station.
Our first train taking us to Chicago was the Empire Builder, one of Amtrak’s iconic long-distance routes, originating in Seattle and slicing across the northern U.S..
We boarded smoothly and easily found two coach seats. At 8:49 a.m., a minute ahead of schedule, we pulled out of Saint Paul, passing the Borealis train waiting on a siding for its later departure. For rail buffs: the Borealis had recently been brought back into service with modern bi-level Superliner cars after corrosion issues temporarily sidelined the original heritage fleet.
As we settled into the rhythm of the train—smooth gliding punctuated by the occasional horn blast—our trip had officially begun. At the Toma WI stop the train crew had pizza delivered for the entire train which was quite a surprise.
After a comfortable day on the rails, we arrived in Chicago and checked into the Midland Hotel, a boutique property in the Loop. Elegant and understated, it was the perfect spot to refresh. That evening we kept it low-key: drinks and appetizers in the hotel bar, then early to bed.
Tuesday greeted us with crisp winds and overcast skies—classic Chicago in early spring. After a relaxed hotel breakfast, we set off in search of a dispensary. Our first stop was closed due to an internet outage, so we pivoted, heading north on the Brown Line to Boystown.
Officially renamed Northalsted, but still widely known as Boystown, the neighborhood remains a historic and culturally rich LGBTQ+ enclave. Rainbow pylons line the sidewalks, and the streets pulse with inclusive energy. Despite the brisk wind slicing through the buildings, we wandered happily.
Our first stop: the historic Ann Sather restaurant. Their cinnamon rolls are legendary—giant, gooey, and served hot alongside a good cup of coffee. It was the kind of cozy pause that turns into a highlight.
Then it was onto Sway Dispensary, a sleek, welcoming cannabis shop with knowledgeable staff and a curated selection. From there, we ducked into Egor’s Dungeon, a legendary adult boutique known for its extensive selection of leatherwear, kink gear, and curiosities you won’t find just anywhere.
As the wind picked up and temperatures dropped, we returned to the Midland to rest before catching the Floridian, Amtrak’s overnight train bound for Washington, D.C. Part of the excitement was timing—the cherry blossoms were in full bloom, and we hoped to catch them at their peak. Though I’d been to D.C. before, I’d never gone as a tourist—never done the monuments, the museums, the reflective walks around the Tidal Basin. This trip was meant to be different. It was about slowing down and finally seeing the city through curious, open eyes.
Quick thinking on Steven’s part got us a room back at the Midland. I barely made it through the overpriced cab ride, and by 11 p.m., finally got a bit of sleep.
There’s nothing worse than being sick away from home and by morning, it was clear: D.C. wasn’t happening. We rebooked our tickets and boarded the Borealis, Amtrak’s new corridor train that connects Chicago to Saint Paul. Designed for comfort and speed, it offers daily service with modern seating, large windows, and a quieter ride.
As the flat Midwestern landscape rolled by, I had time to reflect. Missing D.C. was a disappointment, but the change of plans brought clarity: sleeping in coach on an overnight train isn’t quite as romantic as it sounds. The experience, even cut short, still offered the best parts of rail travel—connection, perspective, and a few good stories. D.C. would have to wait.
✦ How to Use the Amtrak Rail Pass ✦
Thinking of trying an Amtrak adventure of your own? Here’s how to navigate the USA Rail Pass, which Amtrak offers at a discount each year (usually in January):
What It Is:
The USA Rail Pass gives you 10 segments of coach travel over a 30-day period, starting from the day of your first trip.
Segment = One Trip:
Traveling from Point A to Point B counts as one segment. For example, Saint Paul to Chicago? One segment. Chicago to D.C.? Another. (Changing trains mid-route may count as more than one segment.)
Coach Only:
The pass is only valid for coach seating, but many long-distance trains offer roomy seats with leg rests and wide windows. Overnight trips in sleeper cars are not included.
When to Start:
You must start your travel within 120 days of buying the pass. Once the first segment is used, the 30-day clock starts ticking.
Booking:
You must make reservations for each segment, and availability is subject to space. Book early during peak travel periods.
Pro Tip:
Map out your route ahead of time to maximize your segments. Mix long-haul scenic routes with short city-hops for variety.
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