Top Chicago On the Water

Chicago River 90-Minute Architecture Tour

(9,897)

Discover the beauty of Chicago at night during a 1.5-hour cruise on the Chicago River and Lake Michigan. Watch the city sparkle as you pass landmarks such as Museum Campus, Willis Tower, Aon Center and the John Hancock Building, and the illuminated waters of Buckingham Fountain. You'll learn about the history of the city from live commentary by your knowledgeable guide as you glide along the waterfront of Chicago.

from $45

See Chicago's magnificent skyline at night!

Chicago By Night River and Lake Cruise

4.5

(299)

Admire some of the Windy City's most iconic views—and enjoy a time-saving, relaxing way to sightsee—aboard this pet-friendly Chicago River architecture boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including dozens of notable buildings, like the Wrigley Building and the John Hancock Building. In just one tour, you cover multiple branches of the Chicago River and learn insider facts and stories you'd otherwise miss.

from $50

Chicago Architecture River Cruise

(16,005)

1 hour to 1 hour 30 minutesFree Cancellation

from $39

Get a front row perspective on the exquisite buildings that line the Chicago River during a 45-minute architecture cruise. Hear live commentary about the history and architectural heritage of Chicago on this family-friendly tour, which highlights landmarks such as the Chicago Riverwalk, Michigan Avenue Bridge, Wrigley Building, and Willis Tower. Sit on the open-air top deck or the sheltered bottom deck for the ultimate view of Chicago.

Join us in the daytime or evening for City lights and breathtaking views

Chicago River 45-Minute Architecture Tour from Magnificent Mile

(3,148)

45 minutesFree Cancellation

from $28

Take in views of the Chicago skyline and its landmarks during this Lake Michigan sightseeing boat cruise. Enjoy a laidback ride, soaking up panoramic views from this unique perspective. Listen to audio commentary to give you fresh insight into the landmarks you see, like Navy Pier and the Willis Tower, and feel free to bring your own lunch or grab a drink at the onboard bar (own expense).

Lake Michigan Skyline Cruise in Chicago

4.4

(907)

30 to 45 minutesFree Cancellation

from $33

See the towers, piers and iconic landmarks along the Chicago River on an architectural cruise through the heart of the city. Enjoy complimentary refreshments on deck as you cruise down the historic waterway, while listening to fun stories and facts throughout the tour. Spot gargoyles that keep watch high above the city, and buildings that range from Neoclassical to Art Deco. Take in over fifty sites from Lake Point Tower to the Navy Pier, and see the Second City from the water.

Chicago Architectural River Cruise

(817)

City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River

from $50

4.6

(68)

Enjoy a quintessential Chicago experience—and see more of the city's highlights in less time—on an architecture-themed boat tour of the Chicago River. Pick from multiple convenient start times, and board your vessel directly from the Chicago Riverwalk. Thanks to your trained docent guide, receive a rich introduction to the Windy City’s history, key landmarks, and architectural highlights—and spy landmarks like the Marina City towers and Navy Pier from the water’s edge.

from $94

Chicago Architecture Center River Cruise aboard First Lady

4.9

(5,756)

1 hour 30 minutes

from $57

See Chicago from a different perspective on this evening cruise that explores the city’s darker side. As twilight settles over the skyline, glide along the Chicago River while hearing chilling tales of disasters, infamous criminals, and eerie legends tied to the city’s past. This relaxed river cruise blends atmospheric storytelling with some of the best nighttime views of Chicago’s renowned skyline and landmarks. Grab a drink from the onboard bar, settle in, and let the city’s shadowy history unfold as you cruise through the heart of downtown. By the end of the journey, you’ll have experienced Chicago’s skyline in a whole new way—while uncovering the chilling events, legends, and mysteries that shaped the city. Please arrive 30 minutes in advance!

Chicago River Ghost & Dark History Night Cruise

4.0

(110)

from $46

Chicago Lake and River Architecture Tour

(2,320)

See the Second City from the water with a sightseeing cruise along the Chicago River and the Lake Michigan shoreline, offering a unique perspective of towering skyscrapers and historic architecture. This tour offers stories about the city’s history and culture as you pass by Chicago's landmarks, museums, and buildings. Capture unforgettable images of the city skyline from Lake Michigan, ensuring a unique look at Chicago, perfect for all ages.

from $45

Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

(564)

from $46

Chicago River 90-Minute Architecture Boat Tour

(1,640)

Maximize your Chicago sightseeing on a river cruise—and travel aboard a unique historical vessel, which other tours don’t offer—on this one-of-a-kind excursion. Pick from different departure times and board a classic Chicago fireboat, which served the city’s fire department from 1937 to 1981. As you sail Lake Michigan and the Chicago River, view architectural highlights including the Wrigley Building and Chicago Lighthouse, and chart the boat’s firefighting history via the on-board displays and commentary.

from $37

Historical and Architectural Chicago Fireboat River & Lake Cruise

4.9

(262)

from $47

Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"

(20)

1 hour 15 minutes

from $91

Discover Chicago's world-renowned architecture during this sightseeing cruise. Board a comfortable riverboat for a trip down the Chicago River, viewing landmarks like the Willis Tower and the Tribune Tower while listening to in-depth commentary from your guide. Then board a speedboat for an exciting ride up the shore of Lake Michigan for views of Grant Park, the Museum Campus, and other top sights.

Chicago Seadog River & Lake Architectural Tour

4.5

(264)

1 hour 15 minutesFree Cancellation

from $44

Zoom along the shoreline of Lake Michigan, zipping past famous landmarks as you go, during this exhilarating speedboat ride in Chicago. Climb aboard your 2,000-horsepower speed boat at Navy Pier, then hang on for the ride of a lifetime, as you zip past famous attractions like the Willis Tower, Grant Park, and Buckingham Fountain, pausing to learn a little about the history and architecture of the Windy City along the way.

Lake Michigan 30-Minute Speedboat Ride

4.1

(335)

30 minutesFree Cancellation

from $36

Enjoy an unforgettable evening on Lake Michigan with the Chicago Fireworks Cruise. Witness the stunning skyline as you glide across the water, leading up to the spectacular fireworks display at Navy Pier. This 1.5-hour cruise offers a unique perspective of the city while providing a relaxed atmosphere for friends and family to gather and enjoy the show. Boarding begins 15 minutes prior to departure, so arrive early to secure your spot and make the most of this dazzling experience. - 1.5-hour cruise featuring panoramic views of Chicago's skyline - Marvel at the iconic fireworks show off Navy Pier - Departing and returning to 111 N Lake Shore Drive

Chicago Fireboat Fireworks Cruise

394

Kick back and enjoy a great meal while taking in the sights of Chicago's most famed landmarks on this scenic lunch cruise along Lake Michigan. See and photograph the dramatic city skyline, Navy Pier, Soldier Field, and Shedd Aquarium. The cruise includes a delicious buffet lunch with salads, entrees, desserts, and unlimited nonalcoholic beverages. There's also a DJ, games, and a dance floor to keep your group entertained.

from $57

City Cruises Chicago: Signature Lunch Cruise on Lake Michigan

3.9

(351)

Set sail on our flagship vessel, where style meets comfort in a Tiki Chic atmosphere. Your adventure begins on the iconic Chicago Riverwalk, where you’ll board a beautifully appointed boat featuring two climate-controlled decks, two full bars, two bathrooms, and both indoor and outdoor viewing areas—perfect for soaking in the sights no matter the weather. As you sip a refreshing beverage, enjoy the rare experience of transiting the historic Chicago Locks—a must-see for locals and visitors alike. Once you glide into the open waters of Lake Michigan, you’ll be treated to breathtaking views of Chicago’s world-famous skyline, framed by the gentle breeze and city lights. Looking to elevate your cruise? Upgrade to the exclusive Admiral’s Lounge, where you’ll enjoy top-shelf spirits, including selections from the Captain’s Private Reserve, all in a more intimate, upscale setting. This is more than just a boat ride—it’s a uniquely Chicago experience you won’t forget!

from $63

Chicago Skyline Tiki Chic Party Cruise on Lake Michigan

3.8

(27)

1 hour 30 minutes

from $35

Special Offer

4.6

(3,297)

Chicago Crime and Mob Bus Tour

1 hour 30 minutes to 2 hoursFree Cancellation

from

$42

$49

Enjoy a memorable, one-of-a-kind night out on Lake Michigan aboard this combination dinner, dancing, and sightseeing cruise. Make your own way to Navy Pier, and set off as the evening begins. You can admire views of Chicago’s picture-perfect skyline as the sun starts to set. While on board, take advantage of the all-you-can-eat buffet dinner, drinks to purchase, a DJ-helmed soundtrack, and even a fireworks display (weather permitting).

City Cruises Chicago: Fireworks Signature Dinner Cruise

3.9

(85)

2 to 3 hoursFree Cancellation

from $128

Skip navigating around the city with a map and guidebook and explore Chicago's iconic landmarks in just a few hours on this sightseeing tour led by an expert guide. Board a comfortable, large-windowed minibus and explore Downtown and North Side neighborhoods, stopping to visit several locations and hear about the historical and cultural factors that make Chicago unique. Upgrade your tour with a popular open-top boat tour on the Chicago River that focuses on the city's renowned architecture.

Chicago City Tour with Architecture River Cruise Option

(716)

2 to 4 hoursFree Cancellation

from $50

Enjoy waterfront views of downtown Chicago on a 2-hour brunch cruise through the heart of the city. Board a luxurious yacht at Navy Pier then relax on deck with a complementary mimosa. Find a comfortable spot on the three climate-controlled observation decks, and enjoy a sumptuous buffet while the onboard DJ spins a leisurely afternoon playlist. Capture unforgettable images of downtown skyscrapers and architectural landmarks as you navigate along the historic shoreline, then loop back and finish your outing at the bustling Navy Pier.

City Cruises Chicago: Premier Lake Michigan Brunch Cruise

3.8

(27)

Set sail for an unforgettable experience on the water with private boat tours and captained rentals along the Chicago River and Lake Michigan. Whether you're looking to explore the city’s historic waterways or enjoy a relaxing cruise with skyline views, we’ve got you covered. Cruise past iconic landmarks like the Wrigley Building on the Chicago River before heading out to Lake Michigan, where you'll take in panoramic views of the city’s world-famous skyline. With a comfortable and stylish cruiser boat, every ride is smooth, scenic, and uniquely Chicago. Want a custom experience? Choose a private boat rental with a licensed captain—ideal for birthdays, date nights, family outings, or simply relaxing with friends. You enjoy the moment, and we handle the navigation. No boating experience needed. Just bring your favorite snacks, drinks, and good vibes—we’ll provide the boat, the captain, and the unforgettable views. Book now and experience Chicago like never before—from the water!

from $105

2 to 8 hoursFree Cancellation

4.4

(7)

Chicago City Boat Tours

from $299

Per group

1 2 3

Top Attractions in Chicago

1 / 2

Attractions

What are people saying about Chicago

Field Museum of Natural History Admission Tickets

Robert_J, Dec 2025

Get the Extras... worth it!

Even though sometimes it is annoying to have to pay extra for some installations, it is worth it here at the Field. The extra admission (I am sure) helps with the installation and creation of the "extras". We saw "After the Dinosaurs" and the detail, stories, timeline and everything made it a wonderful experience for the family. We used to bring the kids here all the time (from Wisconsin) when they were younger, and now that they are teens they are still fascinated by it all!

Delicious Donuts & City Sights: Chicago's Original Donut Tour

DJ_O, Oct 2025

Great tour every time

This is my favorite tour! I’ve booked it 3 times in the past year and brought new people. It’s always a hit and everyone’s favorite. Aside from the amazing Chicago doughnuts, you get a history of the shops and some of the local building’s you pass on the way. I particularly like that history is more personal and includes nuanced stories that you don’t hear on other tours. I’ve had the same guide all 3 times, Nick, and he is GREAT. He’s funny, personable and makes a point to talk with everyone in the group as we walk around. I highly recommend this tour.

Chicago Seadog River & Lake Architectural Tour

Anastasia_F, Sept 2025

Not your average boat tour!

It was so much fun and very informative! I love that the Seadog is a speedboat and takes passengers out onto Lake Michigan, as well as cruises down the river for the architecture tour. Much more fun than your average tour boat!!! Our tour guide H (I can’t recall his name!) was fantastic and kept us entertained the entire time.

Small-Group Sightseeing Boat Tour in Chicago

Matthew_P, Aug 2025

Perfect ending to a great family trip to Chicgao!

This was an absolute awesome experience! Highly knowlegable and friendly captian! Good mix of excitement and information. Perfect for a family! Way better than one of those crowded commercial river tours...our captain previously worked for one of those and had extensive knowledge! 1000x recommend!