If you want to travel to Minnesota’s Upper Midwest by rail, consider Winona. Winona is a town tucked between the Mississippi River and the Bluffs of Southeastern Minnesota. At the same time, Winona does not see that many big-city visitors; trains do still stop here. The station was built all the way back in 1888, making it an Amtrak depot that is still active today. The services from Winona that travel along the 2,456-mile corridor from Chicago to St. Paul, or from Milwaukee to New York, are covered in this travel guide. For the interested party, this compilation covers the trains to Winona, the time and cost of tickets, how to make a ticket purchase, and some ride hacks.
Why Take a Train to Winona? Top Reasons to Choose Rail Travel
Winona is located along one of the most scenic stretches of the Mississippi River. The scenery on the way to Winona via train is the best. Here are the benefits of taking the train to Winona:
- Scenic river-bluff views: The route along the Mississippi between the Twin Cities and Winona runs right past dramatic bluffs, backwaters, and river towns – a view you simply don’t get from the interstate.
- No driving stress: Skip the 2+ hour drive from Minneapolis-St. Paul or the long haul from Chicago, and just relax, read, or work while the train does the driving.
- Historic depot experience: Winona’s Amtrak station is a beautifully preserved 19th-century building listed on the National Register of Historic Places – arriving there feels like stepping into railroad history.
- Downtown-adjacent arrival: The Winona train station is within walking distance of downtown shops, restaurants, and the riverfront, so you don’t need a rental car once you arrive.
- Affordable compared to flying: There’s no airport near Winona, so the train is often cheaper and simpler than flying into Minneapolis-St. and renting a car.
- Increased frequency: With the added Borealis service alongside the long-running Empire Builder, Winona now has more daily train options than it has in decades.
Note: For weekend getaways, Mississippi River sightseeing, or a relaxed alternative to driving, taking the train to Winona is a genuinely great option.
- Rail travel offers environmental benefits compared to driving and flying. Each passenger creates less carbon when compared to driving or flying for shorter regional trips. Unlike driving, passengers are able to walk around the train and even visit the cafeteria. You can also sit and watch the scenic window next to your seat as the train goes down the tracks. Passengers don’t have to worry about planning rest stops to keep passengers entertained, and there are fewer distractions to stress out parents compared to driving to the Twin Cities metro and around the residents to the Winona area.
- Winona is worth the effort of a rail trip. Passengers get to experience the Victorian-style architecture of the downtown and museums along the river. Passengers have access to trailheads, like the Garvin Heights trail, which is situated on a bluff to overlook the river valley.
- Train passengers are able to get off the train to sightsee instantly, versus everyone else having to find parking. Passengers have some of the local attractions available at their disposal, as opposed to people driving, who get stuck in traffic.
Which Trains Go to Winona? Major Rail Services Explained
Winona is served exclusively by Amtrak, and two separate train routes currently stop there:
| Train Service | Route | Frequency | Key Stops Near Winona |
| Empire Builder | Chicago, IL ↔ St. Paul/Minneapolis ↔ Seattle, WA / Portland, OR | 1 round trip daily | La Crosse, Red Wing, St. Paul |
| Borealis | Chicago, IL ↔ Milwaukee ↔ St. Paul, MN | 1 round trip daily | La Crosse, Red Wing, St. Paul |
- The Empire Builder is a classic example of Amtrak’s long-distance service that runs from Chicago to the Pacific Northwest, including stops at Winona. The service provides coach, hand-seating, and sleeping cars on segments of longer trips.
- The Borealis is a newer, shorter-distance corridor train that was launched in 2024, serving the Chicago to St. Paul corridor. It was designed to provide increased daily rail service along the Mississippi River corridor and also stops at Winona.
- With both services, Winona effectively has two trains a day in each direction. Before, travelers had just the one daily service. Now, passengers have the flexibility of two daily trains.
It’s worth understanding the difference between these two services a bit more, because they serve slightly different types of trips:
- Empire Builder is best suited for travelers going long distances – for example, connecting from Winona all the way out to Fargo, Williston, Havre, Spokane, or the Pacific Northwest, or coming in from Chicago as part of a longer westbound journey. It includes sleeping accommodations for overnight comfort on those longer legs.
- Borealis is purpose-built for shorter regional trips within the Chicago-Milwaukee-La Crosse-Winona-St. Paul corridor. It’s a same-day, no-overnight option, which makes it especially convenient for day trips or weekend visits that don’t require sleeper service.
Note: Since both trains are operated by Amtrak, use the same platform in Winona, and they can be booked on Amtrak.com, booking wise you have to pick the schedule and see if you need a sleeping car.
Popular Train Routes to Winona From Major US Cities
Here’s how travelers from major U.S. cities typically reach Winona by train, along with an approximate sense of travel time. Actual schedules and durations vary by season and train, so always confirm on Amtrak.com before booking.
| Starting City | Route to Winona | Approx. Travel Time | Transfer Required? |
| Chicago, IL | Direct via Empire Builder or Borealis | ~6-7 hours | No |
| St. Paul/Minneapolis, MN | Direct via Empire Builder or Borealis | ~1-1.5 hours | No |
| Milwaukee, WI | Direct via Empire Builder or Borealis | ~4.5-5 hours | No |
| New York City, NY | NYC → Chicago (Lake Shore Limited), then Chicago → Winona | ~24-26 hours total | Yes, at Chicago Union Station |
| Seattle, WA | Direct via Empire Builder | ~1.5 days | No |
| Portland, OR | Direct via Empire Builder | ~1.5 days | No |
| Milwaukee via Wisconsin Dells | Direct via Empire Builder or Borealis | ~5-5.5 hours | No |
Note: For most travelers on the East and West Coasts, the practical path to Winona runs through Chicago, since Chicago Union Station is the hub where both the Empire Builder and Borealis originate.
NYC to Winona Train: Schedule, Duration & Ticket Tips
There’s no single direct train from New York City to Winona – you’ll need to connect through Chicago. Here’s how the journey typically works:
- Leg 1: New York (Penn Station or Moynihan Train Hall) to Chicago Union Station. This is usually done on the Lake Shore Limited, an overnight train that takes roughly 19-20 hours.
- Layover in Chicago. Depending on your connection, you may have anywhere from an hour to a full day between trains at Chicago Union Station.
- Leg 2: Chicago to Winona. Board either the Empire Builder or Borealis, which takes approximately 6-7 hours to reach Winona.
| Leg | Train | Approx. Duration | Overnight? |
| NYC → Chicago | Lake Shore Limited | ~19-20 hours | Yes |
| Chicago → Winona | Empire Builder or Borealis | ~6-7 hours | No |
| Total NYC → Winona | Combined | ~24-28 hours | Partial |
Ticket tips for this route:
- Book both legs together when possible, or at least check connection times carefully – missing a tight connection in Chicago can add a full day to your trip.
- If you want to sleep comfortably on the overnight leg, consider a roomette on the Lake Shore Limited rather than coach.
- Booking well in advance (several weeks to a couple of months ahead) generally secures lower fares, especially in coach class.
- Because this itinerary spans two different train services, fares are usually calculated as separate segments – compare the total cost against flying into Minneapolis-St. Paul and connecting by train or car, since for a one-way NYC-to-Winona trip, flying plus a short regional train hop can sometimes be cheaper and much faster.
Winona Train Travel Tips for First-Time Passengers
If this is your first Amtrak trip to Winona, a few practical tips will make the journey smoother:
- Arrive early. Winona is a smaller station without extensive staffing hours, so arrive at least 15-20 minutes before departure, especially if you need to purchase a ticket in person.
- Bring your own snacks. While the Empire Builder has a café car, the Borealis service may have more limited onboard food options, so pack water and snacks for longer segments.
- Dress in layers. Train cars can run cool, particularly overnight on the Empire Builder.
- Check real-time status. Long-distance trains like the Empire Builder can run late due to freight traffic on shared tracks, so check Amtrak’s status tools before heading to the station.
- Keep boarding passes handy. E-tickets on your phone work fine, but keep a screenshot saved in case of poor cell signal near the river bluffs.
- Know there’s no elevator dependency issue – Winona station is ADA accessible, which is helpful for travelers with mobility needs or heavy luggage.
- Parking is available at the station if you’re starting your trip from Winona rather than arriving there.
- Sign up for text or email alerts. Amtrak offers status notifications, so you know immediately if your train is delayed rather than waiting at the platform without information.
- Pack light. Winona’s station has limited baggage handling compared to major hubs like Chicago Union Station, so a manageable carry-on makes boarding and disembarking much easier.
- Have a backup plan for tight connections. If you’re connecting through Chicago or Milwaukee, build in extra buffer time between trains – long-distance trains occasionally run behind schedule due to shared freight track priority.
- Download the Amtrak app before you travel. It lets you manage your booking, check real-time train status, and pull up your ticket even without a strong signal once you’re underway.
Direct and Connecting Train Routes to Winona
Understanding which routes are direct and which require a connection helps you plan realistic travel times.
| Origin | Direct or Connecting? | Notes |
| Chicago Union Station | Direct | Empire Builder & Borealis both originate here |
| St. Paul Union Depot | Direct | Closest major hub to Winona, ~1-1.5 hrs away |
| Milwaukee Intermodal Station | Direct | Both trains pass through Milwaukee |
| La Crosse, WI | Direct | Neighboring river-town stop just before Winona |
| Red Wing, MN | Direct | Stop just north of Winona along the river |
| New York City | Connecting (via Chicago) | Requires transfer from Lake Shore Limited |
| Boston | Connecting (via Chicago) | Requires transfer from Lake Shore Limited |
| Seattle / Portland | Direct (long-distance) | Same Empire Builder train, opposite direction |
| Los Angeles | Connecting (via Chicago) | Multiple transfers, less practical than flying |
Note: If your starting city is within the Chicago-Milwaukee-St. Paul corridor, you likely have a direct train to Winona. If you’re coming from farther away – the East Coast, South, or West Coast (outside the Empire Builder’s own line) – you’ll almost always connect through Chicago.
Business Class vs Coach on Winona Trains
Seating options differ slightly depending on which train you’re riding.
| Feature | Coach Class | Business Class (Borealis) | Sleeper (Empire Builder, long segments) |
| Seat type | Standard reclining seats | Wider seats, more legroom | Private roomette or bedroom |
| Price | Lowest fare | Moderate upgrade over coach | Highest fare, includes meals |
| Best for | Short trips (Chicago-Winona, St. Paul-Winona) | Travelers wanting extra comfort on corridor trips | Overnight, multi-day travel (e.g., toward Seattle/Portland) |
| Available on | Empire Builder & Borealis | Borealis only | Empire Builder only |
| Amenities | Power outlets, tray tables | Priority boarding, extra space, complimentary snack in some cases | Private space, bedding, dining car access |
- For a simple Chicago to Winona or St. Paul to Winona day trip, coach class is sufficient and will save you the most money. If you are on the Borealis and do not mind spending a little extra to have more space, business class is a good option. Sleeper accommodations will not save you any time or money on the short trip to Winona as opposed to other spots on this route, like if you continue on the Empire Builder towards Fargo, Havre, Spokane, Seattle, or Portland.
- When you are debating between coach class or business class on the Borealis, think about how long your trip will be and your personal comfort level. For a short segment, like St. Paul to Winona, the time you spend in your seat is so short that most travelers will be okay in coach. For the longer segment of Chicago to Winona, the business class cabin is more comfortable and has a bigger seat for travelers who want to work or sleep during the trip. Also, business class tickets can often be discounted and used to earn rewards, which means that business class upgrades usually cost the traveler less than expected.
Winona Train Station: Everything You Need to Know About Chicago Union Station → Winona Station (WIN)
The Winona Amtrak Station (station code: WIN) is one of the most historically significant small-town depots on the entire Amtrak network.
| Detail | Information |
| Station code | WIN |
| Location | Winona, Minnesota, along the Mississippi River |
| Built | 1888, by the Chicago, Milwaukee, St. Paul and Pacific Railroad |
| Historic status | Listed on the National Register of Historic Places (2013) |
| Platforms | 1 side platform, 2 tracks |
| Accessibility | ADA accessible |
| Parking | Available on-site |
| Trains served | Empire Builder, Borealis |
| Proximity to downtown | Short walk to downtown Winona shops and restaurants |
| Notable history | Historically visited by prominent figures,s including sitting U.S. presidents passing through on speaking tours. |
- To reach Winona from Chicago Union Station, take the Empire Builder or Borealis out of Union Station on Canal Street. It’s one of the USA’s oldest and busiest train stations. After departing, you’llcontinuep north on the Empire Builder or Borealis through Wisconsin, passing Milwaukee and all of the other towns listed, crossing into Minnesota at La Crosse before arriving in Winona.
- Chicago Union Station has everything you need. There are ticket counters, a Metropolitan Lounge for first-class passengers, plenty of food options, and other Amtrak routes to connect you to other parts of America. It is a great departure point from any starting location to get to Winona.
- Winona station is exactly what you’d expect: a small station with a small waiting room and no shops or restaurants. This is part of the appeal. The original architecture was built in 1888, with maple flooring andwoodworkk bringing passengers back in time to when the Milwaukee Road’s Hiawatha Service spanned Chicago and the Twin Cities. Because of the small size of the station, it’s easy to spot the train and station staff.
How to Book Train Tickets to Winona: Step-by-Step Guide
Booking a train ticket to Winona is simple and can be done in a few minutes:
- Go to Amtrak.com or open the Amtrak app. This is the official and most reliable source for schedules and fares.
- Enter “Winona, MN (WIN)” as your destination and your departure city as the origin.
- Select your travel date(s). For round trips, choose both outbound and return dates to see combined pricing.
- Compare available trains. You’ll typically see Empire Builder and/or Borealis options with departure and arrival times listed.
- Choose your class of service – Coach, Business (where available), or a sleeping accommodation for longer connecting segments.
- Review the fare and any add-ons, such as bringing a bike or checking baggage.
- Enter passenger details and payment information to complete your booking.
- Save your e-ticket to your phone or print it, and note your train number and departure time.
- Arrive at the station early, especially if you need to check luggage or purchase last-minute items.
Note: Booking directly through Amtrak avoids third-party booking fees and gives you access to real-time schedule changes and refund/exchange policies directly from the source.
A few extra booking notes worth knowing:
- Flexible vs. saver fares: Amtrak often offers multiple fare tiers on the same train. A “Saver” fare is cheaper but usually non-refundable, while a “Flexible” fare costs more but allows free changes or cancellations – useful if your travel dates aren’t locked in yet.
- Group and multi-city bookings: If you’re traveling with several people or building a multi-city itinerary (for example, New York → Chicago → Winona → return), you can add each leg within the same booking flow on Amtrak.com.
- Mobile ticketing: Amtrak’s e-tickets work directly from your phone, so there’s no need to print anything unless you prefer a physical copy.
- Special assistance: If you need wheelchair assistance, have a service animal, or require other accommodations, you can note this during booking or by calling Amtrak customer service in advance, so station staff are prepared.
- Cancellation windows: Refund and change policies vary by fare type, so review the fare rules shown at checkout before finalizing your purchase, especially for Saver fares.
Winona Train Ticket Price: How Much Does It Cost & How to Save Money
Amtrak uses dynamic pricing, meaning fares to Winona change based on how far in advance you book, the day of the week, and overall demand – similar to airline pricing. That said, here’s a general sense of what travelers have historically paid on popular routes to Winona:
| Route | Typical Coach Fare Range (One-Way) | Notes |
| St. Paul → Winona | ~$20-$35 | Short regional hop, often the cheapest ticket |
| Chicago → Winona | ~$40-$90 | Price varies significantly by day and advance purchase |
| Milwaukee → Winona | ~$35-$70 | Mid-range regional fare |
| NYC → Winona (via Chicago) | ~$120-$250+ | Combined multi-leg fare, higher due to overnight segment |
Note: Prices are illustrative and fluctuate – always check Amtrak.com for current, accurate fares before planning your budget.
Tips to save money on Winona train tickets:
- Book early. Fares tend to rise as the travel date approaches and seats fill up.
- Travel midweek. Tuesday-Thursday departures are often cheaper than Friday/Sunday travel.
- Watch for Amtrak promotions. Amtrak periodically runs sales, companion fares, or discounted rail pass deals.
- Consider a rail pass if you’re planning multiple trips in the Midwest – this can reduce the per-trip cost significantly.
- Check student, senior, military, and AAA discounts, which Amtrak offers on many fares.
- Avoid peak travel windows like major holidays when demand (and prices) spike.
- Compare Empire Builder vs. Borealis fares for the same day – since they’re separate services, pricing can differ even for a similar Chicago-to-Winona itinerary.
- Sign up for Amtrak Guest Rewards. It’s free to join, and points earned on train travel can be redeemed for future ticket discounts, which adds up if you plan to visit Winona more than once.
- Bundle with a return ticket rather than booking two separate one-way fares, as round-trip pricing is sometimes more favorable depending on the route and dates.
- Be flexible with departure times. If your schedule allows it, comparing the Empire Builder’s departure time against the Borealis departure time on the same day can reveal a meaningful price difference.
Best Time to Visit Winona by Train: Seasonal Travel Tips
Winona’s riverside setting and bluff scenery change dramatically with the seasons, and each has its own appeal for train travelers.
| Season | Highlights | Travel Considerations |
| Spring (Apr-May) | Blooming bluffs, fewer crowds, mild weather | Occasional rain; check for weather-related delays |
| Summer (Jun-Aug) | Riverfront activities, warm weather, longest daylight for scenic views | Peak tourist season – book tickets earlier |
| Fall (Sep-Oct) | Stunning autumn colors on the bluffs, arguably the most scenic time to ride the train | Very popular for leaf-peeping trips – fares can rise |
| Winter (Nov-Mar) | Quiet, snow-covered river scenery, lower fares | Cold temperatures; occasional weather delays on the route |
- For scenic value, early-to-mid fall is widely considered the best time to take the train to Winona, as the bluffs along the Mississippi turn vibrant shades of red and gold. For budget-conscious travelers, winter weekdays typically offer the lowest fares and the fewest crowds, though you should build in extra buffer time for potential weather delays.
- If you’re planning your trip around a specific event, keep in mind that Winona hosts several seasonal festivals – including summer riverfront events and fall arts and culture happenings – that can affect both hotel availability and how full the trains are. Booking your ticket a few weeks ahead of any local festival weekend is a smart move, since both the Empire Builder and Borealis can sell out on high-demand dates.
Train vs Bus vs Car to Winona: Which Is the Best Way to Travel?
Here’s how the three main travel options compare for a trip to Winona:
| Factor | Train | Bus | Car |
| Scenery | Excellent – river and bluff views | Limited, highway-focused | Good, but you’re driving, not sightseeing |
| Cost | Moderate | Usually cheapest | Depends on gas, tolls, and parking |
| Comfort | High – space to move, walk, use restroom | Moderate – fixed seating | Depends on vehicle and driver fatigue |
| Flexibility | Fixed schedule, limited daily departures | Fixed schedule, sometimes more frequent | Fully flexible, go anytime |
| Downtown access | Station is within walking distance of downtown Winona | Varies by stop location | Requires parking, but full mobility once there |
| Stress level | Low – no driving or traffic | Low to moderate | Higher, especially on long drives |
| Best for | Scenic, relaxed travel; no-car trips | Budget travelers | Travelers needing a car once in Winona |
Bottom line: If scenery, comfort, and a relaxed experience matter most, the train is the best choice for reaching Winona – especially from Chicago, Milwaukee, or the Twin Cities. If budget is the top priority and you don’t mind a less scenic ride, a bus may be cheaper. If you need a vehicle for exploring the surrounding bluff country and small towns once you arrive, driving offers the most flexibility, though you’ll trade away the relaxed, scenic rail experience.
- A middle-ground approach that many travelers take: take the train one way so you can relax and take in the scenery. Then rent a car in Winona when you arrive. You can explore the surrounding areas such as La Crescent, Lanesboro, or the Root River bluff country. This way, you get the best of both worlds. You arrive in a relaxed, scenic way, and you have freedom and flexibility when you arrive.
- Winona doesn’t have its own commercial airport, so flying is rarely a consideration for travelers, as the closest major airport is about 2 hours away,y which is why the St. Paul Union Depot direct train is a popular option for people who travel a great distance.
Frequently Asked Questions
1. Is there a direct train to Winona, Minnesota?
Yes. Winona is served directly by Amtrak’s Empire Builder and Borealis trains, both of which stop at the Winona station (station code WIN) without requiring a transfer if you’re departing from Chicago, Milwaukee, or St. Paul.
2. What is the train station code for Winona?
The Amtrak station code for Winona is WIN.
3. How long does the train from Chicago to Winona take?
The trip from Chicago to Winona typically takes around 6 to 7 hours on either the Empire Builder or Borealis, depending on the specific schedule and any freight-related delays.
4. Can I take a train from New York City to Winona?
There’s no direct train, but you can connect through Chicago. You’d ride the Lake Shore Limited overnight from New York to Chicago, then transfer to the Empire Builder or Borealis for the final leg to Winona. Total travel time is roughly 24-28 hours.
5. How much does a train ticket to Winona cost?
Prices vary with demand, but short regional trips like St. Paul to Winona often range from about $20-$35 one-way, while longer trips like Chicago to Winona can range from roughly $40-$90 one-way. Booking early generally secures lower fares.
6. Where is the Winona train station located?
The historic Winona Amtrak station is located along the Mississippi River in downtown Winona, Minnesota, within walking distance of local shops, restaurants, and the riverfront.
7. Does the Winona train have Wi-Fi and food service?
The Empire Builder includes a café car with food and beverages for purchase. Onboard amenities on the Borealis may be more limited, so it’s a good idea to bring your own snacks for shorter regional trips.
8. Is the Winona train station wheelchair accessible?
Yes, the Winona Amtrak station is ADA accessible, with accommodations for passengers with mobility needs.
9. What’s the best time of year to take the train to Winona?
Early-to-mid fall is considered the most scenic time to visit, thanks to vibrant autumn colors along the bluffs. Winter weekdays often offer the lowest fares for budget-conscious travelers.
10. Is it cheaper to take the train or drive to Winona?
It depends on your starting point. For short regional trips (like from St. Paul), the train is often comparably priced to driving once you factor in gas and parking. For longer trips, driving may be cheaper overall, but the train offers a more relaxed, scenic experience without the stress of navigating traffic.