Chicago, the biggest city in Illinois, was built on a river, and the best way to understand its skyline is still from the water. From May to October, the Chicago River and the Lake Michigan shoreline fill with every kind of boat: narrated architecture cruises past more than 50 landmark buildings, water taxis running between Navy Pier and Union Station, a 1930s fireboat, pedal-powered cycleboats, electric boats you drive yourself, tiki party boats and speedboats racing along the lakefront.
Choosing the right one is harder than it looks, and few people have tried more of them than Pooja Naik. Mumbai-born and Chicago-based, she is the creator behind The Chicago Pescetarian, where she covers the city’s food, sports, travel and lifestyle scene, from new restaurants and hidden gems to local experiences, for more than 140,000 followers.
Summer on the water is one of her favorite ways to see the city, and here she shares which boats she recommends, from the classic first-timer’s architecture tour to the ones she books with friends.
The best Chicago architecture boat tour for first-time visitors
One of my favorite ways to experience Chicago in the summer is from the water, and I’ve tried everything from architecture cruises to party boats and smaller private experiences.
For a classic Chicago architecture experience, Wendella Architecture Boat Tours is one of my favorites. It’s a great choice for first-time visitors because you get the iconic river views while learning the stories behind Chicago’s architecture and skyline. I recommend booking in advance, especially for weekends and sunset cruises during the summer, as those times can be particularly popular.
“Seeing Chicago from the water gives you an entirely different appreciation for the city.”
So many ways to see Chicago from the water
That said, one of the things I love about Chicago is that there are so many different ways to experience the city from the water depending on the kind of day you want.
An affordable ride on the river: Shoreline Water Taxi
Shoreline Water Taxi is a great option if you want a more affordable, casual way to get out on the river while also using it to get around the city. It isn’t an architecture tour, but you still get some fantastic views of downtown from the water.
A piece of Chicago history: Chicago Fireboat Tours
For something completely different, Chicago Fireboat Tours offers one of the city’s more unique boating experiences aboard a historic fireboat, combining Chicago history with time on the river and lake.
Boats for friends: Chicago Cycleboats and electric Duffy boats
If you’re traveling with friends, I’ve also really enjoyed experiences like Chicago Cycleboats and an electric Duffy boat, where the appeal is less about a formal tour and more about having your own relaxed experience on the water with a group. The Duffy boat in particular is a fun option if you want something smaller and more private where you can cruise at your own pace.
Party boats and mimosa cruises
For a livelier experience, there are Island Party Boat cruises and mimosa river cruises, which are great for groups looking to make the boat ride itself part of the celebration.
Speed and skyline: Seadog
And if you want something faster-paced, Seadog is a fun way to combine skyline views with more of a thrill ride.
My biggest tip: pick the boat for the day you want
“Don’t think of Chicago boat experiences as one-size-fits-all.”
My biggest tip for visitors is not to think of Chicago boat experiences as one-size-fits-all. If architecture is your priority, choose a dedicated architecture cruise like Wendella. But if you’ve already done the classic architecture tour, or you’re visiting with friends and want something more social, there are so many other ways to experience the river and lake. No matter which you choose, seeing Chicago from the water gives you an entirely different appreciation for the city.
When to book a Chicago boat tour
For summer visits, I recommend booking your preferred experience in advance, particularly for weekends, sunset times and larger groups.
Pooja’s Chicago boats: where to find them
Wendella Architecture Boat Tours
Chicago’s original architecture boat tour company, with 45- and 90-minute river tours and a river-and-lake tour through the Chicago Lock. Address: 400 N Michigan Ave, at the Wrigley Building and DuSable (Michigan Avenue) Bridge · wendellaboats.com
Shoreline Water Taxi
Unnarrated water taxis every 20–30 minutes, usually May to September, between Navy Pier, Michigan Avenue and Union Station/Willis Tower on the river, and Navy Pier, Buckingham Fountain and Museum Campus on the lake. Address: Michigan Avenue dock, 401 N Michigan Ave, plus stops across downtown · shorelinesightseeing.com
Chicago Fireboat Tours
Tours aboard the Fred A. Busse, which served the Chicago Fire Department from 1937 to 1981, from Lake Michigan through the locks onto the river. Address: DuSable Harbor, 111 N Lake Shore Dr
Chicago Cycleboats
Pedal-powered, BYOB cycleboat cruises on the river, plus electric and vintage boat rentals. Address: 155 N Riverwalk, between the LaSalle and Wells Street bridges · chicagocycleboats.com
Electric Duffy boats: Chicago Electric Boat Company
Duffy electric boats you drive yourself or hire with a captain, from Marina City and the Riverwalk. Address: 300 N State St, Marina City · chicagoelectricboats.com
Island Party Boat
Polynesian-themed tiki boats for private groups on the river and lake. Address: 355 E Riverwalk South
Seadog
30-minute lakefront speedboat rides and a thrill-ride version from Navy Pier. Address: Navy Pier, Dock Street, 600 E Grand Ave
Chicago Boat Tour Companies: Architecture Cruises, Water Taxis and More
- Wendella Tours & CruisesPooja’s pickThe original Chicago architecture boat tour, 45 or 90 minutes on the river or river and lake.
- Chicago’s First Lady CruisesThe official Chicago Architecture Center river cruise, led by expert docents.
- Shoreline SightseeingPooja’s pickArchitecture and lake tours, plus the Shoreline Water Taxi around downtown.
- Mercury, Chicago’s Skyline CruiselineFamily-friendly river and lake cruises, including the Canine Cruise.
- Chicago Fireboat ToursPooja’s pickHistory and architecture tours aboard a 1930s Chicago fireboat.
- Chicago CycleboatsPooja’s pickPedal-powered BYOB cruises for groups, plus electric boat rentals.
- Chicago Electric Boat CompanyPooja’s pickSelf-drive or captained Duffy electric boat rentals.
- Island Party BoatPooja’s pickPolynesian-themed tiki party boats for private groups.
- Seadog (City Cruises)Pooja’s pick30-minute speedboat thrill rides along the lakefront.
- City Cruises: Spirit of Chicago & OdysseyLunch and dinner cruises on Lake Michigan.
- Tall Ship WindySailing and fireworks cruises on a 148-foot topsail schooner.
- Kayak ChicagoGuided kayak architecture tours and rentals on the river.
Most tours run from spring to fall; book ahead for summer weekends and sunset departures.
Plan the rest of your Chicago trip
Most boats leave from the river downtown, so it pays to sort the logistics first. If you’re driving in, SpotHero lets you reserve a garage near the docks in advance; on foot and by train, Citymapper handles the L and the buses. For skip-the-line tickets to Chicago’s museums and observation decks, see our Headout review, and for everything else on your phone, our best travel apps.
Beyond the city, our Illinois guide and USA state guides cover where to go next.
