Daily · + Hiawatha finisher
Chicago to Minneapolis–St. Paul
Chicago → Minneapolis–St. Paul
Six to eight nights from Minneapolis–St. Paul to a Chicago finish.
- Recommended
Nights - 6–8
- Cities
- 3
- Lines
- 2
Fly in MSP · Fly out ORD
The route
Tap a stop to jump
- Minneapolis–St. Paul2 nights · Days 1–2
- Borealis · 6h 15m
- Milwaukee2 nights · Days 4–5
- Hiawatha · 1h 30m
- Chicago3 nights · Days 6–8
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Days 1–2 · 2 nights
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 · Minneapolis–St. Paul
The Saint Paul Hotel
Rice Park, St. Paul · $$$
1910 grande dame overlooking Rice Park, a ten-minute walk from Union Depot. Old-school doorman service and exactly the arrival you want after a long flight.
Do · Minneapolis–St. Paul
Summit Avenue mansion walking tour
Four and a half miles of America's best-preserved Gilded Age street. F. Scott Fitzgerald grew up at 599 Summit; the Governor's mansion is a few doors down.
A couple more in Minneapolis–St. Paulwe’d consider
For when the top pick’s full or the wrong fit.
Hotel 340
$$Cathedral Hill, St. Paul
Converted 1917 St. Paul Athletic Club on the hill between downtown and Summit Avenue. Walking distance to the Cathedral and Grand Avenue.
Check rates on Booking.com →
The Celeste of St. Paul Hotel & Bar
$$Lowertown, St. Paul
Boutique hotel inside a 1911 former convent, two blocks from Union Depot. Cocktail bar downstairs is quietly one of the best in Minneapolis–St. Paul.
Check rates on Booking.com →
Also worth it
- Cathedral of Saint Paul — free and modelled on St. Peter's. The dome is the view from half the city.
- Mississippi River Boulevard bike path south to Minnehaha Falls.
- Cathedral Hill and Grand Avenue for dinner — brownstone streets, proper restaurants.
- Green Line light-rail over to Minneapolis for an afternoon — same ticket, 40 minutes door-to-door.
Getting around: METRO light rail connects MSP to downtown St. Paul in about 70 minutes — Blue Line from the airport to Target Field, then a cross-platform Green Line east. One $2.50 ticket covers the transfer. Inside the city, the A Line BRT and Green Line cover most of what matters.
Metro Transit (Minneapolis–St. Paul) →Amtrak · Borealis
One-way · single seat
Depart
Minneapolis–St. Paul
MN
Rail
Arrive
Milwaukee
WI
Board the Borealis at St. Paul Union Depot mid-morning. Six and a quarter hours southeast through the St. Croix River bluffs, La Crosse, the sandstone gorges around the Dells, and the lakes country into Milwaukee. The Empire Builder runs the same corridor once daily if the schedule fits better.
Journey time
6h 15m
Days 4–5 · 2 nights
Milwaukee
A lakefront, a Calatrava, and a frozen custard culture that is legitimately the reason to come.
Stay · Milwaukee
The Pfister Hotel
Downtown · $$$
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.
Do · Milwaukee
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. The collection inside is stronger than it has any right to be for a city this size.
A couple more in Milwaukeewe’d consider
For when the top pick’s full or the wrong fit.
Kimpton Journeyman Hotel
$$$Third Ward
Boutique Kimpton in the heart of the Third Ward's restaurant and gallery district. Rooftop with lake and skyline views.
Check rates on Booking.com →
Saint Kate — The Arts Hotel
$$Downtown / Theater District
Every room has original art, guitars, and sketchbooks. Across from the Marcus Performing Arts Center.
Check rates on Booking.com →
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.
Getting around: The Hiawatha arrives at Milwaukee Intermodal Station, which is right downtown. MCTS buses and the Hop streetcar (free) handle the rest. The Third Ward and lakefront are easy walks.
Milwaukee County Transit (MCTS) →Amtrak · Hiawatha
One-way · single seat
Depart
Milwaukee
WI
Rail
Arrive
Chicago
IL
Seven daily departures, 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 · 3 nights
Chicago
Three nights to land in, eat properly, ride the L, and board a flight home without rushing any of it.
Stay · Chicago
Virgin Hotels Chicago
River North · $$$
North edge of the Loop at the Wabash bridge — a short walk across into River North, and an equally short walk to the architecture cruise dock, the West Loop dinner scene, and the Blue Line back to O'Hare.
Do · Chicago
Chicago Architecture Center river cruise
Ninety minutes on the river with a docent who actually knows what they're looking at — and the deepest education in 'why Chicago looks the way it does' you'll get for $50. Book before you land; it sells out in summer.
A couple more in Chicagowe’d consider
For when the top pick’s full or the wrong fit.
Chicago Athletic Association Hotel
$$$The Loop
Converted 1890s gentlemen's club facing Millennium Park. Library bar, game room, Cindy's rooftop — worth the stay on its own.
Check rates on Booking.com →
The Palmer House Hilton
$$The Loop
One of the oldest continuously operating hotels in America. The lobby ceiling fresco alone justifies the room rate.
Check rates on Booking.com →
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, no reservations, wait for it.
- Lakefront Trail on a Divvy bike — 18 miles of traffic-free waterfront.
- The Green Mill in Uptown for jazz in a room Al Capone drank in.
Getting around: CTA Blue Line runs O'Hare to the Loop in 45 minutes for $5. The Red, Brown, and Green lines cover nearly everything else downtown. Don't get a rental.
Chicago Transit Authority (CTA) →Getting there
How to arrive at the start of the trip
Whichever way you’re coming. Pick the panel that fits.
Arriving from Europe
MSP runs seasonal Delta direct service from London Heathrow (typically May–October) and year-round one-stop service via Amsterdam, Paris, Frankfurt, or Reykjavík. Most arrivals are afternoon-to-evening US time.
Customs at MSP is reliably faster than at O'Hare, but you still don't want to chase the same-day Borealis after a transatlantic flight. Overnight in St. Paul; the Borealis runs once daily mid-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 is usually priced the same as a round-trip out of either airport. 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. Many travelers park at MSP airport's economy lot (around $14/day) and ride light rail in — same Blue/Green Line two-seat ride airline arrivals use.
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 runs daily mid-morning out of St. Paul Union Depot — six and a quarter hours to Milwaukee. The Empire Builder runs the same corridor once daily as the overnight Seattle service; either works, but the Borealis lets you board after a night's sleep.
- 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 sandstone gorges, and the Wisconsin lakes country opens up on the left side 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.
- If you miss the train, Amtrak will rebook you on the next Borealis (or Empire Builder) the same day at no charge. Different rules from European rail; less stressful.
- Amtrak's luggage allowance is generous: two carry-ons plus two personal items free, plus free checked bags on long-distance trains. Far more lenient than European rail or budget airlines.
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: pick one up at MSP arrivals (Mint, T-Mobile prepaid, or your carrier's roaming plan if cheaper). 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 with a 6–8-hour eastward shift 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 for about $21 at least 72 hours before you fly.
Good to know
- Travelling 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 through the sandstone gorges, and reboard the next day. That's the 8-night version of the trip.
- MSP → St. Paul is about 70 minutes on light rail for $2.50 (Blue Line to Target Field, cross the platform, Green Line east). Still cheaper and usually faster than a taxi in rush hour.
- When to go: May through October. September is perfect — harvest at the wineries and crisp mornings on the river.
Not this trip?
There’s a corridor for every weekend.
5–6 nights · ORD → STL
Chicago to St. Louis
Five to six nights down the Lincoln Service. Chicago, Illinois farmland, and the Arch.
5 nights · ORD → DTW
Chicago to Detroit
Five nights, two American classics, and a reborn 1913 Beaux-Arts train station to walk into.
5–6 nights · ORD → GRR
Chicago to Grand Rapids
Three nights in Chicago, then the train curves east and Lake Michigan appears through the window.