Three daily departures
Chicago to Detroit
Chicago → Detroit
Five nights, two American classics, and a reborn 1913 Beaux-Arts train station to walk into.
- Recommended
Nights - 5
- Cities
- 2
- Line
- 1
Fly in ORD · Fly out DTW
The route
Tap a stop to jump
- Chicago3 nights · Days 1–3
- Wolverine · 5h 30m
- Detroit2 nights · Days 4–5
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Days 1–3 · 3 nights
Chicago
Three nights to land, cruise, eat deep-dish in the right neighborhood, and board the Wolverine without feeling rushed.
Stay · Chicago
The Freehand Chicago
River North · $
Affordable, walkable to River North and the Brown Line, and the Broken Shaker bar downstairs is a legitimate cocktail spot — not a hotel bar that happens to pour drinks.
Do · Chicago
Chicago Architecture Center river cruise
The canonical Chicago experience. Book it for the afternoon of day one so you're oriented for the rest of the stay.
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 — Impressionist wing, two hours, don't try to do both buildings.
- Pequod's or Lou Malnati's for deep-dish.
- Lakefront Trail on a Divvy bike — 18 miles traffic-free.
- The West Loop for dinner — Au Cheval or Girl & the Goat.
Getting around: CTA Blue Line from O'Hare to the Loop in 45 minutes for $5. Don't get a rental.
Chicago Transit Authority (CTA) →Amtrak · Wolverine
One-way · single seat
Depart
Chicago
IL
Rail
Arrive
Detroit
MI
Chicago Union Station to Detroit's New Center Amtrak station. The approach across Michigan fruit country is a proper daytime rail ride. From New Center it's a ten-minute rideshare (or a DDOT bus) down to Corktown — drop your bags at Shinola and the restored 1913 Michigan Central tower is the first place you walk into.
Journey time
5h 30m
Days 4–5 · 2 nights
Detroit
A city that rebuilt itself three times. The current version is by far the most interesting.
Stay · Detroit
Shinola Hotel
Downtown / Woodward · $$$
Detroit's flagship design hotel from the city's most iconic modern brand. Walking distance to everything downtown; San Morello on the ground floor is dinner sorted.
Do · Detroit
Detroit Institute of Arts + Motown Museum
The DIA has Diego Rivera's Detroit Industry frescoes — one of the great works of the 20th century, in a city that paid for it. Motown is ten minutes away in a clapboard house on Grand Boulevard.
A couple more in Detroitwe’d consider
For when the top pick’s full or the wrong fit.
The Siren Hotel
$$Downtown
Restoration of the 1926 Wurlitzer Building. Candy Bar is a classic room-key martini stop, and the hotel is walking distance to Broadway and the waterfront.
Check rates on Booking.com →
Detroit Foundation Hotel
$$$Downtown
Former Detroit Fire Department HQ turned boutique. The Apparatus Room takes its name from the original fire-truck bay.
Check rates on Booking.com →
Also worth it
- Michigan Central Station in Corktown — the 1913 Beaux-Arts tower Ford restored in 2024, public lobby well worth a second look after the first-day walk-through.
- Eastern Market on Saturday morning.
- QLine streetcar up Woodward to Midtown.
- Buddy's Pizza for Detroit-style square slices.
Getting around: QLine streetcar runs Woodward from downtown to Midtown. DDOT and SMART buses cover the rest. SMART FAST Route 261 runs direct to DTW airport in about 45 minutes for $2.
Detroit Department of Transportation (DDOT) →Getting there
How to arrive at the start of the trip
Whichever way you’re coming. Pick the panel that fits.
Arriving from Europe
Direct daily flights to ORD from London, Dublin, Frankfurt, Paris, and Amsterdam, plus secondary European hubs. Most arrivals are afternoon-to-evening US time.
Don't try to do the Wolverine same-day. Customs at O'Hare Terminal 5 plus the CTA ride into the Loop eats half an afternoon, and the Wolverine departures are spread across the day. Overnight in Chicago first; you have three nights there anyway.
Flying home from DTW: Delta runs daily direct service to Amsterdam (the trip's natural one-stop home), and one-stop options through ATL, JFK, or AMS reach virtually every European hub. ESTA before you leave home — apply at least 72 hours before your outbound flight.
Connecting flight from elsewhere in the US
ORD is a hub for both United and American — non-stop service from virtually every major US airport.
Open-jaw ORD-in / DTW-out is usually priced the same as a round-trip out of either airport. DTW is a Delta hub with strong non-stop coverage of the eastern and central US, so the back end of the trip is easy to fly home from.
Driving in, or already nearby
Driving from elsewhere in the Midwest: Chicago Union Station's parking garage sits one block south of the station entrance, around $30/night. Reserve via SpotHero or ParkWhiz for a meaningful discount on the gate price.
Already on Amtrak elsewhere: the Hiawatha runs hourly from Milwaukee, the Borealis / Empire Builder feed in from St. Paul, and the Lake Shore Limited connects from the East Coast. All deliver to the same Chicago Union Station the Wolverine departs from.
Practicalities
Booking and onboard
- The Wolverine runs three daily departures Chicago → Detroit. The afternoon train (typically the 1:00 or 2:30 PM) puts you into New Center in time for dinner at San Morello.
- Book two to three weeks ahead. The Wolverine is one of the busier midwestern corridors and trains do fill on Friday afternoons and Sunday evenings.
- Café car only on the Wolverine — sandwiches, coffee, decent enough but pricey. Pack from a deli in the Loop on your way to Union Station for a five-and-a-half-hour ride.
- Wi-fi is spotty across rural Indiana and Michigan; cell signal varies. Treat the ride as scenery time and plan to read.
- If you miss the train, Amtrak rebooks you on the next Wolverine the same day at no charge — three departures means there's almost always one within a few hours. 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.
- Detroit's Amtrak stop is the small New Center station, not the restored Michigan Central. MCS is a ten-minute rideshare south — treat it as your first stop in Detroit, not your arrival hall.
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 O'Hare on arrival (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 near Union Station 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
- SMART FAST Route 261 runs Detroit downtown ↔ DTW in about 45 minutes for $2 — the single best airport transit bargain in the Midwest.
- Detroit summer weekends host festivals on the riverfront most weeks — worth checking the calendar if you're flexible on dates.
- When to go: May through October. Summer weekends Detroit runs festivals nearly every weekend on the riverfront.
Not this trip?
There’s a corridor for every weekend.
6–8 nights · MSP → ORD
Chicago to Minneapolis–St. Paul
Six to eight nights from Minneapolis–St. Paul to a Chicago finish.
5–6 nights · ORD → STL
Chicago to St. Louis
Five to six nights down the Lincoln Service. Chicago, Illinois farmland, and the Arch.
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.