Chicago has a $10 secret — the Chicago Water Taxi — and I’m about to put you on.
The Chicago Water Taxi runs right down the Chicago River — downtown to Chinatown, Michigan Avenue to the West Loop — for ten dollars one-way. Ten dollars. For skyline views that people pay $50+ to get on an architecture cruise.
I’ve ridden it more times than I can count, and here’s what I tell everyone: pair it with a downtown staycation and you have the perfect fall day in Chicago. No flight, no planning stress, just a really good day.
THE CHICAGO WATER TAXI RIDE
The water taxi is run by Wendella (the same folks behind the architecture tours, so you know it’s legit) (click here to book a Wendella boat ride). It runs March through late November, so fall is prime time — the leaves along the river are doing the most right now.
The main route hits Michigan Avenue, Clark Street, the Ogilvie/Union Station area, and Chinatown. My move: board downtown, ride it end to end just for the views, then hop off in Chinatown for lunch. Or ride it at golden hour and watch the city light up from the water. Either way, it’s the best ten dollars you’ll spend this fall.
Pro tip: it runs on a schedule, not on demand, so check the day’s departures before you head to the dock. Weekends are the move — less commuter crowd, more leisure energy.
THE STAYCATION
Here’s where it becomes a whole thing. Book a downtown hotel for the night, ride the taxi during the day, and come back to a room with a view. These are stays I’d book with my own money:
Loews Chicago Hotel — Streeterville, right by the river. The rooftop scene here is elite and you’re steps from a water taxi dock.
Radisson Blu Aqua — That wavy Aqua building you see in every Chicago skyline photo. The rooms are spacious, the location is unbeatable for a downtown weekend.
LondonHouse Chicago — The rooftop here at sunset? Unmatched. Curio Collection, so it has that boutique feel without the boutique price tag.
Book the room, ride the river, eat well. That’s the whole itinerary and honestly it’s better than most vacations I’ve taken.
MAKE A DAY OF IT
Morning: Board the water taxi downtown. Ride to Chinatown, grab lunch — dim sum, boba, the works.
Afternoon: Ride back, hop off at Michigan Avenue. Walk the Riverwalk, pop into shops, act like a tourist in your own city.
Evening: Check into your hotel, freshen up, dinner somewhere with a view. Rooftop if the weather’s cooperating.
That’s it. Ten-dollar taxi, one hotel night, zero flights. The perfect fall Chicago day.