Chicago's Most Beloved River Boat Tours Showcase The Stunning City Skyline And Iconic Architecture

Chicago is a Midwest destination positively brimming with some of the world's best architecture. From turn-of-the-century masterpieces by Louis Sullivan, known as "the father of skyscrapers," to the instantly recognizable corncob-like double towers of Marina City, there's no shortage of amazing structures — and views — in the Windy City. Of course, there are numerous ways one can enjoy Chicago, whether on foot, via sightseeing bus, or from the raised tracks of the iconic "L." But to really experience the grandeur of Chicago's skyline and its layered histories, you definitely shouldn't miss the opportunity to see the city from the water. For an extra special treat, visit during St. Patrick's Day, when the river glows bright green!

There are a few tourist traps to avoid in Chicago, but the Chicago River is undoubtedly one of the most scenic features of its namesake city. It's also the result of astonishing feats of engineering. It actually flows backwards, away from Lake Michigan and through a series of canals totaling 156 miles on its way to the Mississippi River. This is thanks to 19th-century efforts to keep the water from becoming contaminated by reversing the flow. Today, the river shimmers as it glides under scenic bridges, next to skyscrapers, and alongside a popular riverwalk. In the River North neighborhood, one of its canals is even home to the world's first floating eco-park with boardwalks, paddling, and wildlife. And it's also one of the best ways to see the city, thanks to a number of fantastic cruises that highlight unique landmarks and Chicago history.

It probably goes without saying that if the Chicago Architecture Center (CAC) leads river tours, you're bound to get some of the best insights into the city's built history. Aboard Chicago's First Lady, an elegant vessel with plenty of above- and below-deck seating, you'll be treated to a showcase of the city's architecture, including some of its most famous addresses and under-the-radar Chicago gems. Enthusiastic CAC docents introduce myriad buildings, stylistic periods, and influential figures that made the skyline what it is today. Tours run at multiple points throughout the day between March and November, for 90 minutes at a time. Depending on the date and schedule, tickets for general boarding start at $56. Priority boarding options are also available, usually adding $15-20 to the price. They include not only an early boarding period but admission to the Chicago Architecture Center located just across E. Wacker Drive from where the First Lady docks.

First Lady, which is also home to Mercury Cruises, has been family-owned and operated for four generations, offering some of Chicago's best tours since 1934. The first architecture tour embarked in 1993, and the company continues to be one of the top-rated river cruise outfits on Tripadvisor. Additionally, First Lady provides other sightseeing cruises, like a river and lake combination tour which also runs at nighttime, plus the city's first canine cruise, so Fido won't miss out on the fun. A visitor who hopped aboard in August 2025 enthused on Tripadvisor, "Incredibly knowledgeable guide. Not only did we get the history of the architecture, we heard about the people behind it, and the efforts to clean and protect the Chicago river. Very interesting!"

Shoreline Sightseeing boasts the largest fleet of boats in Chicago, with a total of 18 vessels. Operating tours since 1939, the company knows a thing or two about providing a great tour experience, so you'll be able to learn about the history, architecture, and lore of Chicago from energetic, well-informed guides. One of the most popular trips is the 75-minute architecture tour, a slightly shorter route than the one offered by the Chicago Architecture Center but also a little bit friendlier to the pocketbook, with adult fares starting at $40.95. Boarding from either Navy Pier or Michigan Avenue, the tour heads down all three branches of the Chicago River to take in more than 40 landmarks, from the most iconic to the hidden gems. And if you prefer to hear about Chicago's famous sites en español, hop aboard the Spanish-language architecture tour.

Along with river cruises, Shoreline Sightseeing also offers a Skyline Lake Cruise and a Fireworks Cruise. The latter takes in the fireworks launched from Navy Pier, Chicago's "year-round playground," on Wednesday and Saturday evenings. And for a unique way to commute to different places around the city, book a day pass for the hop-on, hop-off water taxi service, which connects you to major highlights via docks at Union Station, Michigan Avenue, Navy Pier, and the Museum Campus — home to the Shedd Aquarium, Field Museum, Adler Planetarium, Soldier Field, and numerous other memorials and pavilions. One visitor who enjoyed a tour with her family in August 2025 enthused on Tripadvisor, "The tour guide was amazing with so many interesting insights. Fun and informative. Drinks were a nice option. I would definitely recommend." And if you're planning to visit multiple top attractions in Chicago, save on Shoreline Sightseeing's architecture tour when you purchase a CityPASS.

While several cruise companies in Chicago offer scenic jaunts to view Navy Pier's famous summertime fireworks, Wendella also offers a 45-minute river cruise option to see the nighttime show framed by the city's soaring skyscrapers. And of course, that's only one of several wonderful tours you can take with this company that's been in the business for nine decades. Along with daily 90-minute and 45-minute architecture cruises, Wendella also offers a combo experience in the form of the Lake & River Cruise, which gives you an up-close view of some of the city's most iconic structures before heading out into the open waters of Lake Michigan to take in the stunning skyline from a little farther afield. "We really enjoyed this tour," a visitor who hopped aboard in August 2025 writes on Tripadvisor. "It was a beautiful day on the water. Phyllis, the tour guide was outstanding! We saw lots of beautiful buildings and learned about their history and their architecture. Highly recommend it!"

Competition is stiff when it comes to architecture tours in the city, with many outfits leading great trips, and Wendella is no exception. If you're looking for an extra little treat, though, look no further. On Thursdays, a 2-hour Wine & Cheese Cruise starts along the river before heading through the Chicago Harbor Lock and into Lake Michigan. Included in the fare, which is $70 per person as of this writing, you'll be able to sample a selection of hors d'oeuvres and wine. And as it's an adults-only cruise, you'll be able to fully relax as you take in the skyline and sip a good vintage or two.

When the infamous Chicago Fire of 1871 roared through the city, it swept over an area one mile wide and four miles long. It took out an astounding 17,500 buildings, which at the time were primarily constructed of wood. When the "Great Rebuilding" commenced pretty much immediately afterward, fireproof materials like brick, limestone, and marble were put into use. Not only were these materials better for safety, they were immensely strong and could support buildings that towered many stories higher than their predecessors. During Tours & Boats' highly rated architecture tour, learn about the modern city that sprang from the ashes, along with contemporary landmarks that have come to define the Windy City. "Our tour guide Hillary was amazing!" a visitor raved in a Tripadvisor review after cruising in August 2025. "Super informative but in a fun, interactive way. Highly recommend. She pointed out hidden facts and answered all our questions."

Tours & Boats' cruise runs for 90 minutes and highlights different artistic styles that characterize the banks of the Chicago River, from elaborate early 20th-century stone facades to marvels of engineering. Tours aboard the "Summer of George" vessel typically run between May and October and depart from River City Marina. Adult fares are $49, and group discounts are also available when traveling with 10 or more people. Ready to party? If you're looking to host a unique event, private charters can accommodate up to 150 passengers, with options like a full-service bar, catering, and entertainment in addition to the built-in panoramic views of Chicago's skyline.

If looking at history on the Chicago River banks isn't quite enough to appease the history buff in you, step aboard the "Fred A. Busse," a bright red, 1937 fireboat. Depart from DuSable Harbor in Lake Michigan, just off Lake Shore Drive, a one-of-a-kind waterfront road that highlights some of the world's best architecture. From there, you'll glide into the river on a family-friendly outing to experience the city's colorful history and architecture. Along with expert commentary about the buildings you'll float by, learn about the history of the Chicago Fire Department. The vessel is actually rather like a floating museum, chock full of firefighting artifacts and photos of the "Fred A. Busse" when it still had firefighters stationed onboard. The ride lasts about 90 minutes, with tickets ranging from $22 for children aged four to 12 to $40 for adults.

It's hard to beat a boat tour where you can enjoy a scenic, educational outing and have a brewski, too! One cruise you won't find elsewhere in Chicago is Fireboat Cruises' Brew Cruise with Phase Three Brewing, which runs every Thursday evening during the summer. Phase Three Brewing, which has two locations in the city, supplies locally made, exciting new releases during this 2-hour sunset excursion that traverses both lake and river. "First time doing a sunset tour and we could not have asked for a better experience," one visitor raved in a Google review in May 2025. "The captain and his crew were very knowledgeable about the boat and its history." Chicago Fireboat Cruises also offers lake-only tours, including excursions to take in Navy Pier's fireworks, the sunset, and a special two-day opportunity to immerse yourself in the annual Chicago Air & Water Show.

Between late May and late August, when Navy Pier's fireworks light up the night sky, enjoy an experience that's both relaxing and awe-inspiring with Chicago Line Cruises. Lightly narrated, this Wednesday evening excursion is a treat for 90 minutes and includes a spell along the river and then a trip out onto Lake Michigan to take in the pyrotechnics. The company also offers an architecture-specific tour that highlights everything from the iconic, angled Wrigley Building to the mammoth Merchandise Mart. 

Complimentary coffee, tea, lemonade, and soft drinks are available onboard, so you can cool down on a Chicago Line Cruise if it's a hot summer day or cozy up if you happen to experience why they call it the Windy City! Alcoholic beverages are also available for purchase throughout the tour. And if a good spirit is more your style, don't miss the Whiskey Tasting River Boat Tour, which launches every second Friday between June and September. The trip includes an open whiskey bar with a guided tasting to complement the stunning views of the city. Or tip a glass of a different sort during a Wine Tasting tour, which embarks every first Friday of the month during the summer.

Visitors have really enjoyed the enthusiastic and well-informed docents who made the trip a memorable one with Chicago Line Cruises. And an international visitor who took the cruise on a spring day in 2025 had a good tip in his 5-star review on Tripadvisor: "The tour lasts 90 minutes — it can get really cold on board if the weather's not in your favour, and Chicago's weather can change by the hour so keep an eye on the forecast." 

It pretty much goes without saying that any Chicago River cruise is going to offer great views of the city's unique architecture, spanning late 19th-century brick and "greystone" buildings to 20th-century gothic gems to postmodern masterpieces from the 1980s and 1990s. Aboard a Chicago River Boat Architecture Tour, presented by Empire Tours and Productions, you'll be guided on a tour of more than 50 buildings that really make Chicago shine, presented by expert docents who are historians or even architects themselves. This trip lasts for 90 minutes, and tours run hourly every day of the week. One visitor shared in a Tripadvisor review that she enjoyed the docent's style and being on a smaller vessel. "Our guide made the experience. She was very knowledgeable and humorous."

At 6 p.m. every day, you can opt in to a cocktail cruise, which wraps the architecture tour up into a neat bundle with craft cocktails, wine, and beer available for purchase from a full bar. Tickets for adults are $49, and kids six years and older ride for $30 — children under six are free! Another summertime favorite is the fireworks excursion, where you can enjoy Navy Pier's pyrotechnics display on Wednesdays. The standard architecture tour is included, with complimentary soft drinks available in addition to a full bar. Fares for this special combo are $65 for adults and $49 for kids six years and older. Combo tours are a bit of a specialty for this company, which also offers a walking tour called "Chicago's Secret Interior," which takes you inside some of the city's most iconic addresses. You can also combine a luxury minibus tour with a river boat cruise for the full experience on both land and water. The 3.5-hour bus-cruise option is available twice daily.

If large vessels and narrated tours aren't exactly your cup of tea — and you've got a bit of a DIY streak — look no further than Chicago Boat Company. This outfit rents small watercraft that you can take on your own self-directed cruise along the river. Or, for something social and totally different, join a Cycleboat tour for either 1.5 or two hours. The pedal-powered vessels can accommodate up to 16 people, making it both a great group outing or something fun to do as a couple. As of this writing, it's $65 per adult and BYOB. "The ride up and down the Chicago River was great!" one recent participant raved on Tripadvisor. "We celebrated, played our tunes, and had a wonderful time. Monica and Marie were GREAT captains! Fun and professional! Will definitely do it again!"

Chicago Boat Company also offers a couple of unique, small-scale tours that depart from the riverwalk and take a different spin around the river. Aboard another small craft, join either a 2-hour guided ghost tour or history tour. These tours are intentionally kept small so you can experience personalized interactions with your guide, who will answer any question you have about the Windy City's long — and haunted — past.

Chicago River cruises are among the most enjoyable trips you can take during a visit to the city, and many return again and again. To narrow down the best river cruises that emphasize the city's unique skyline and history, we researched each company's specific offerings, focusing especially on architecture tours. We also took into account additional trips that made certain cruises stand out, like dog-friendly tours, Spanish language options, or unique food and drink tasting cruises. We also consulted honest reviews and ratings on Google, Yelp, and Tripadvisor from visitors who had recently hopped aboard for Chicago River journeys, highlighting experiences that received at least 4.5 stars. In many cases, these companies have been running for decades and have amassed thousands of reviews, which helped to steer our list.