Daily · + Hiawatha finisher
Minneapolis–St. Paul to Chicago by train
Minneapolis–St. Paul → Chicago
The Borealis and the Empire Builder, Milwaukee's lakefront, and a Chicago finish.
- Cities
- 3
- Lines
- 2
Fly in MSP · Fly out ORD
The route
Tap a stop to jump
- Minneapolis–St. PaulDays 1–2
- Borealis · 6h
- MilwaukeeDays 4–5
- Hiawatha · 1h 30m
- ChicagoDays 6–8
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Book the trip
Everything you need, up top
Celeste of St. Paul · $$ · Summit Avenue and the James J. Hill House
The Pfister Hotel · $$$ · Milwaukee Art Museum (Calatrava wings)
Chicago Athletic Association · $$$ · Chicago Architecture Center river cruise
Trains
Borealis · Hiawatha
The train
Minneapolis–St. Paul to Chicago by train
- Trains
- Amtrak Borealis and Empire Builder
- Trains a day
- 2 in each direction (one of each)
- Runs
- Every day
- Journey time
- About 7¾ hours; St. Paul to Milwaukee about 6
- From St. Paul
- Empire Builder in the morning, Borealis late morning
- Stations
- St. Paul Union Depot → Milwaukee Intermodal → Chicago Union Station
- Stops on the way
- Including Red Wing, Winona, La Crosse, Wisconsin Dells and Milwaukee
- Milwaukee–Chicago
- Also the Hiawatha, up to 7 a day, about 1½ hours
Chicago to Minneapolis–St. Paul by train
Going north, the Borealis leaves Chicago Union Station late in the morning and the Empire Builder in the afternoon; both take about eight hours to St. Paul Union Depot. The METRO Green Line starts outside the depot and runs to downtown Minneapolis.
From Amtrak’s published timetable, checked 7 October 2026. These trains run every day; times can differ on some days and change with each new timetable, so confirm the times for your date on amtrak.com before you book.
Days 1–2
Minneapolis–St. Paul
The older, quieter twin. A Beaux-Arts cathedral, F. Scott Fitzgerald's childhood streets, and a river that actually bends through the city.
Stay
Celeste of St. Paul
Downtown St. Paul (Rice Park) · $$
Boutique hotel in a former convent (the old St. Agatha's Conservatory) in downtown St. Paul, near Rice Park — about a mile from Union Depot, so a short ride or a 20-minute walk from the train.
Check rates on Booking.com →Know your dates?
Or consider
- Hewing Hotel$$$ · Rates →
North Loop, Minneapolis
- The Marquette Hotel, Curio Collection$$ · Rates →
Downtown, Minneapolis
Do
Summit Avenue and the James J. Hill House
Four and a half miles of Victorian-era mansions — billed as the longest preserved stretch in the country. F. Scott Fitzgerald finished his first novel at 599 Summit; the Governor's Residence is further up at 1006. Start at the James J. Hill House — the railroad baron's mansion, with guided tours Thursday to Sunday, January to November; MNHS also runs Summit Avenue walking tours on select dates.
Details at mnhs.org →Also worth it
- Cathedral of Saint Paul — free and modelled on St. Peter's. The dome is the view from half the city.
- Mississippi River Boulevard bike path south to Minnehaha Falls.
- Cathedral Hill and Grand Avenue for dinner — brownstone streets, proper restaurants.
- Green Line light-rail over to Minneapolis for an afternoon — same ticket, about 45–50 minutes.
Amtrak · Borealis
One-way · single seat
Depart
Minneapolis–St. Paul
MN
Rail
Arrive
Milwaukee
WI
Board the Borealis at St. Paul Union Depot late in the morning. About six hours southeast along the Mississippi River bluffs and Lake Pepin, across at La Crosse, past Wisconsin Dells and through the lakes country into Milwaukee. The Empire Builder runs the same corridor once daily, leaving St. Paul earlier in the morning, if that fits better.
Journey time
6h
Days 4–5
Milwaukee
A lakefront, a Calatrava, and a frozen custard culture that is legitimately the reason to come.
Stay
The Pfister Hotel
Downtown · $$$
1893 grande dame with the largest Victorian art collection of any hotel in the world. Blu rooftop bar is a Milwaukee institution — go at sunset.
Check rates on Booking.com →Know your dates?
Or consider
- Kimpton Journeyman Hotel$$$ · Rates →
Third Ward
- Saint Kate — The Arts Hotel$$ · Rates →
Downtown / Theater District
Do
Milwaukee Art Museum (Calatrava wings)
Santiago Calatrava's Quadracci Pavilion (2001) has moving sunshade 'wings' that open at 10, flap at noon, and fold back down at 5. Time your visit (they stay shut in high wind). The museum is closed Mondays and Tuesdays.
Details at mam.org →Also worth it
- Leon's Frozen Custard on 27th Street. Not optional.
- Milwaukee Public Market in the Third Ward for a market lunch.
- Pabst Mansion tour — the beer barons lived well.
- Lakefront Trail walk from the Art Museum north to Bradford Beach.
Amtrak · Hiawatha
One-way · single seat
Depart
Milwaukee
WI
Rail
Arrive
Chicago
IL
Up to seven departures a day, 90 minutes, reserved seating. The Hiawatha is the closest the US has to a proper European regional train — cheap, frequent, and it drops you at Union Station with an afternoon to spare.
Journey time
1h 30m
Days 6–8
Chicago
Three nights to land in, eat properly, ride the L, and board a flight home without rushing any of it.
Stay
Chicago Athletic Association
The Loop · $$$
An 1893 Venetian Gothic athletic club facing Millennium Park, about a 20-minute walk from Union Station. Close to the Art Institute and the architecture cruise dock, and a short walk to the Blue Line back to O'Hare.
Check rates on Booking.com →Know your dates?
Or consider
- The Palmer House Hilton$$ · Rates →
The Loop
- Freehand Chicago$ · Rates →
River North
Do
Chicago Architecture Center river cruise
Ninety minutes on the river with a docent who actually knows what they're looking at — the best short course in 'why Chicago looks the way it does'. Book before you land; it sells out in summer. The season runs mid-March to late November.
Details at architecture.org →Also worth it
- The Art Institute. Thursday opening, Impressionist wing, two hours, a coffee across the street after.
- Deep-dish at Pequod's (Lincoln Park) — caramelised crust; reserve ahead or expect a wait.
- Lakefront Trail on a Divvy bike — 18 miles of traffic-free waterfront.
- The Green Mill in Uptown for jazz in a room with Prohibition-era legend attached.
Getting there
How to arrive at the start of the trip
Whichever way you’re coming. Pick the panel that fits.
Arriving from Europe
Delta flies MSP nonstop from London Heathrow, Paris and Amsterdam, with Dublin, Rome, Reykjavík (Icelandair) and Frankfurt (Discover) in season. Most arrivals are afternoon-to-evening US time.
You don't want to chase the same-day Borealis after a transatlantic flight. Overnight in St. Paul; the Borealis leaves once daily in the late morning, so you board on day two refreshed.
Flying home from ORD: direct service to most major European hubs daily. ESTA before you leave home — apply at least 72 hours before your outbound flight.
Connecting flight from elsewhere in the US
MSP is a Delta hub — non-stop service from virtually every major US airport plus extensive regional service across the Upper Midwest. If you're flying connecting via Atlanta, Detroit, or Salt Lake City, inbound options are plentiful.
Open-jaw MSP-in / ORD-out tickets are worth pricing against a round trip. Worth checking either direction depending on schedule.
Driving in, or already nearby
Driving from elsewhere in the Upper Midwest: St. Paul Union Depot has a small parking garage that gets tight on weekends. Some travelers park at an MSP airport lot and ride in on the Route 54 bus or the Blue/Green Line light rail.
Already on Amtrak elsewhere in the network: the Empire Builder feeds in from Seattle, Portland, and Glacier National Park, but that's a 24–36-hour ride. The Empire Builder eastbound from Whitefish or Spokane is a worthwhile multi-day add-on if you have the time, otherwise this trip is best started fresh in St. Paul.
Practicalities
Booking and onboard
- The Borealis leaves St. Paul Union Depot once daily in the late morning — about six hours to Milwaukee. The Empire Builder covers the same corridor once daily, leaving St. Paul earlier in the morning; check amtrak.com for current times.
- Book two to three weeks ahead. Both trains run short (4–5 cars) and weekend departures fill, especially with summer Dells traffic.
- Sit on the left leaving St. Paul. The Mississippi tracks the route through the bluffs, and the Wisconsin lakes country opens up past Wisconsin Dells.
- Café car on the Borealis — sandwiches, coffee, decent enough but pricey. Pack from a deli in St. Paul before you board. The Empire Builder's overnight version has a proper dining car included with sleeper-class fares.
- Wi-fi is sporadic across central Wisconsin; cell signal varies by carrier. Treat the ride as a six-hour reading window.
- Don't count on a free rebooking if you miss your train: under Amtrak's rules a no-show can forfeit the value of that ticket. If your plans change, change or cancel before departure — Flexible fares refund in full, Value fares only in part.
- Amtrak's carry-on allowance is generous: one personal item plus two carry-on bags free. Checked baggage is only offered on some trains and at some stations — check yours before you travel.
First time in the US?
- Tipping: 18–20% on restaurant bills (some places now add it automatically — check the bill), $1–2 per drink at bars, a few dollars per bag for porters and housekeeping.
- US SIM card: buy a prepaid SIM or eSIM before you fly (or check your carrier's roaming plan). US wi-fi is strong; hotel and coffee-shop networks cover most of the gaps.
- Cash is rarely necessary — tap-to-pay works at most US restaurants, transit, and shops. Carry $40 in small bills for tips and the occasional cash-only spot.
- Jet lag across a 6–7-hour time difference is real. Don't try to power through your first day — book a hotel in St. Paul and sleep when your body says.
- ESTA, not a visa, for most EU and UK passports. Apply online at esta.cbp.dhs.gov ($40.27) at least 72 hours before you fly.
Good to know
- Traveling with kids? Wisconsin Dells — the self-styled Water Park Capital of the World — makes a strong family add-on. Get off at the Dells platform on day 3, stay one night at Great Wolf Lodge, ride the Original Wisconsin Ducks (March to early November), and reboard the next day. That's the 8-night version of the trip.
- MSP → St. Paul: the Route 54 bus takes about 25 minutes; light rail takes about an hour (Blue Line into downtown Minneapolis, then the Green Line east). Either is cheaper than a taxi and often as fast in rush hour.
- When to go: May through October. September is perfect — harvest at the wineries and crisp mornings on the river.
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