Best Chicago Boat Tours: Lake and River Cruises 2023

The Local Tourist
9 min readJul 26, 2023


Best Chicago Boat Tours: Lake and River Cruises 2023

May 26, 2023 by Theresa Goodrich

Taking one of the many Chicago boat tours is a delightful way to experience the Windy City.

Chicago Seadog speedboat tour on the Chicago River

What’s the best way to experience Chicago in summer?

On a boat.

Chicago boat tours give you spectacular views of the incredible skyline. They help you experience Chicago’s legendary architecture and famous landmarks.

As the Third Coast, Chicago has miles of shoreline. We’ve also got the Chicago River, which flows through downtown, giving the city its unique character.

During the summer months, the river teems with tour boats and Lake Michigan is decorated with the silhouettes of countless sails. The water becomes an essential part of experiencing the city.

There are three branches of the Chicago River that flow through the heart of the city, and you can experience them during an architectural boat tour. You’ll learn how the river itself is a piece of history and the stories behind many of the iconic buildings in downtown Chicago.

You’ll discover several of the city’s major attractions. Sail past Grant Park and the iconic Buckingham Fountain. Learn more about the Museum Campus and its world-renowned museums.

There are unique boat tours, too. Have a party aboard a tiki-themed boat, and get the best view around of the twice-weekly fireworks. Take a private sailboat tour. Speed across Lake Michigan on a jetboat.

You can find your perfect cruise of Chicago waterways, whether it’s your first time visiting or you’re a born-and-bred local.

Ready to take one of these Chicago boat tours? We’ve included several below, including architecture cruises, sunset cruises, and unique Chicago experiences.

Prices listed below are for one adult, unless it’s a private charter.

Cruise aboard Chicago's First Lady with River City and Willis Tower in the background. One of the many Chicago boat tours you can take in the Windy City.

Chicago Boat Tours

Several of these tours are available for purchase through Viator, of whom The Local Tourist is an affiliate. If you book one of these cruises, we’ll get a small commission. It’s at no extra cost to you and helps support our small business.

More articles to help you explore Chicago:

Chicago Architecture Boat Tours

Chicago Architecture Center River Cruise aboard Chicago’s First Lady

Take the #1 boat tour in North America aboard Chicago’s First Lady. Chicago Architecture Center River Cruise is the gold standard among all Chicago architecture tours.

90-minutes fly by as you’re led by expert docents.

View of LondonHouse Chicago from Chicago's First Lady on the Chicago River.
LondonHouse Chicago from the Chicago River

You’ll learn about a mix of historic and modern architectural styles, including the people who designed and built Chicago.

I’ve personally taken these Chicago River boat architecture tours multiple times, and every time I learn something new.

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  • Duration: 1 hour 30 minutes
  • Price: from $57.00

Shoreline Sightseeing Chicago Architecture River Cruise

Since 1939, Shoreline Sightseeing has been plying Chicago’s waters and they have the largest fleet in the city. Their architecture river tours are one of the most popular, with over 10,000 5-star ratings on Viator.

This architecture-centric 75-minute river tour takes you down the river’s main branch past Tribune Tower and the Merchandise Mart (now theMART) and up the north branch to the East Bank Club.

You’ll then float south past iconic landmarks like the Willis Tower (or, as we call it, the Sears Tower) to the old Post Office Building.

Shoreline Sightseeing boats docked at Navy Pier with the Centennial Wheel above.  They have some of the most highly rated Chicago boat tours

With Shoreline’s Chicago boat tours, you’ll enjoy the magnificent city skyline and more than 40 notable buildings, including the John Hancock Center and the Wrigley Building. Tour guides fill you in on their distinctive architecture.

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  • Duration: 1 hour 15 minutes
  • Price: $50.36

Chicago Lake and River Architecture Tour

This comprehensive tour from Wendella cruises both the Chicago River and Lake Michigan, weaving a story of more than 200 years of social, cultural, and political history.

Starting with the internationally-known architecture from the Chicago River, you’ll venture through the Chicago Lock onto Lake Michigan for views of Chicago’s extraordinary skyline.

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  • Duration: 1 hour 30 minutes
  • Price: $42.00

45-Minute Chicago River Architecture Tour

This 45-minute Chicago River cruise from Magnificent Mile introduces you to the city’s rich history and architectural heritage. Your expert guide highlights the best of Wendella’s full-length architecture tours.

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  • Duration: 45 minutes
  • Price: $27.00

Tours & Boats Chicago Architecture Boat Tours

Tours & Boats specializes in architecture tours on the Chicago River and Lake Michigan. These take place on the Summer of George, which docks at River City Marina. They also rent it out for private charters.

Don’t let the price of this 90-minute tour fool you; it’s got a 5-star rating from hundreds of verified customers.

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  • Duration: 1 hour 30 minutes
  • Price: $32.00

Chicago River Boat Architecture Tour

Chicago Line Cruises hosted the first architectural river cruise in Chicago in 1980, and they’ve been going strong every since.

In this 90-minute tour, you’ll discover the architects who built Chicago’s magnificent skyline. You’ll also learn about the devastation of the Great Chicago Fire and how it transformed the city.

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  • Duration: 1 hour 30 minutes
  • Price: from $59.00

Premier Chicago River Architectural Lunch Cruise

Enjoy Chicago’s architecture in comfort as you enjoy a chef-prepared, plated lunch, and sip on creative cocktails aboard the Odyssey.

The interior is climate-controlled and there’s an open-air outdoor deck. This architectural lunch cruise offers great views and a narrated tour tracing the city’s history from the water.

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  • Duration: 2 hours
  • Price: from $110.58

Chicago Sunset Cruises

Lake Michigan Sunset Cruise

Get ready for a tranquil journey on Lake Michigan with Wendella’s Sunset Cruise. The tour kicks off near the DuSable (Michigan Avenue) Bridge, onboard Wendella’s premium tour boats.

The cruise sails from the Chicago River, through the Chicago Lock, and into the open waters of Lake Michigan. Enjoy a breathtaking sunset view behind the city.

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  • Duration: 1 hour 30 minutes
  • Price: $42.00

Chicago Signature Dinner Cruise on Lake Michigan

The Chicago Signature Dinner Cruise on Lake Michigan provides an array of experiences. Dine from a buffet prepared by an onboard chef while appreciating the stunning views of the city.

Departing from Navy Pier, you’ll see iconic sights such as the Willis Tower and Adler Planetarium from a unique perspective.

Enjoy the convenience of a full-service bar, and consider taking your experience outdoors on the open-air rooftop decks.

With dancing and live DJ entertainment on deck, the cruise creates a remarkable ambiance for an unforgettable evening.

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  • Duration: 3 hours
  • Price: $136.54

Private Sunset Sail on Lake Michigan

With the Private Sunset Sail on Lake Michigan, you get an exclusive sailing experience. Sail along Chicago’s scenic lakefront with up to five friends, captained by a US Coast Guard licensed professional.

The journey presents stunning views of Chicago’s skyline. With a private charter, you can personalize everything — from the guest list to music and sailing route.

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  • Duration: 2 hours
  • Price: $483.96 per group

Chicago Fireworks Cruises

Private Evening Sail in Chicago Ending with Navy Pier Fireworks

Set off on a private sailboat cruise in Chicago, culminating in a stunning fireworks display at Navy Pier.

Navy Pier Fireworks

This two-hour experience provides incredible views of the city skyline. Make this your unique, customizable experience, right down to the music and guest list.

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  • Duration: 2 hours
  • Price: from $542.82 per group

Chicago Lake Michigan Fireworks Cruise

Embrace summer in Chicago with Wendella’s unforgettable fireworks cruise on Lake Michigan. Every Wednesday and Saturday night, the sky above the city bursts into a spectacular show.

Don’t miss out on an unobstructed 360-degree view of this vibrant spectacle.

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  • Duration: 1 hour
  • Price: from $50.00

Unique Chicago Boat Tours

30 Minute Lake Michigan Speedboat Ride

Embrace the thrill of a speedboat tour on Lake Michigan. This exciting adventure promises a unique perspective of Chicago’s iconic skyline.

Your journey begins at Navy Pier, which is the launch point for the Lakefront Speedboat Tour. It’s one of the best ways to view Chicago from the water.

Your experience on Seadog Cruises will be both fun and informative. As you speed along the shoreline, you’ll hear entertaining insights about the world-famous Chicago skyline.

The whole family, including your furry friend, is welcome aboard this 30-minute adventure.

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  • Duration: 30 minutes
  • Price: from $36.39

Chicago River Tiki Boat Cruise

Experience Chicago in a unique and relaxing way aboard a floating Tiki Bar.

As the cruise navigates the picturesque Chicago River, you can sit back, enjoy a beverage, and take in the sights and sounds of the city.

Chicago Island Party Boat Tiki Boats on the Chicago River

For those curious about the impressive buildings lining the river, like the distinctive Marina City or the gleaming white Wrigley Building, the cruise’s staff is ready to provide interesting details.

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  • Duration: 1 hour 15 minutes
  • Price: from $35.00

Lake Michigan Tiki Bar Cruise

Step aboard a vessel that epitomizes Tiki Chic. With two climate-controlled decks, two bars, two bathrooms, and a superior sound system, the cruise promises a comfortable and stylish journey.

Indulge in the “Admirals Lounge,” featuring top-shelf alcohol including the captain’s private reserve.

The journey begins on the Chicago Riverwalk, leading you through the unique experience of the Chicago Locks.

Once out on Lake Michigan, the cruise provides stunning views of Chicago’s skyline. This 1 hour and 30-minute journey showcases Chicago in a way guests won’t forget.

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  • Duration: 1 hour 30 minutes
  • Price: from $35.00

Chicago Fireboat Tours

Take a tour about a piece of Chicago history. The Fred A. Busse served the Chicago Fire Department for 44 years before becoming an excursion boat in Door County, Wisconsin.

Now it navigates the Chicago River transporting visitors through the city’s past. The veteran-owned company hosts tours led by expert docents with multiple departure times daily.

Because Chicago Fireboat Tours dock in DuSable Harbor and enter the Chicago River through the locks system, tour times vary from 90 minutes to 2.5 hours.

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  • Duration: 90 minutes to 2.5 hours
  • Price: $40

Skyline Tour Aboard 148 Ft. Schooner Tall Ship Windy

Step aboard the 148 Ft. Schooner Windy for the Skyline Tour — a leisurely trip around Lake Michigan. You’ll escape the city’s hustle and bustle and explore Chicago’s shores while taking in the world-famous skyline.

At 148 feet long, the Schooner Windy is one of the few 4 masted Schooners built in the United States. You’ll enjoy a relaxing sail around aboard this truly historic vessel.

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  • Duration: 1 hour 15 minutes
  • Price: $59.00

Sail Tall Ship Windy, Chicago’s Official Flagship 148′ Schooner

Leave the city behind and immerse yourself in an Educational Tour and Sail aboard the Windy 148′ Schooner, Chicago’s Official Tall Ship.

During the 75-minute sail, you’ll learn about sailing, the history of Lake Michigan, and Chicago.

The ship’s history is tied to Lake Michigan’s sailing history, filled with unique stories and interesting facts.

You’ll also have the chance to help sail this famous Schooner, all while enjoying incredible scenery and photo opportunities.

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  • Duration: 1 hour 15 minutes
  • Price: $39.00

Originally published on The Local Tourist: Best Chicago Boat Tours



The Local Tourist

Born to write with a nearly obsessive love of travel, history, cooking, Chicago, and my husband. Author, speaker, exuberant lover of life.