Top Chicago Cruises &amp; Sailing

Chicago Architecture River Cruise

1 hour to 1 hour 30 minutesFree Cancellation

4.8

(16,044)

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

45 minutesFree Cancellation

Drink in a one-of-a-kind perspective on the Windy City when you go for an evening cruise, perfectly timed to coincide with the sunset. Hop aboard your open-top vessel (with an enclosed and climate-controlled lounge) in the heart of the Magnificent Mile, and cruise along the Chicago River. Then, see the skyline from a distance, and watch the skyscrapers light up, when you continue to Lake Michigan for a sunset viewing.

(3,180)

from $28

Lake Michigan Sunset Cruise in Chicago

Discover the architectural gems of the Windy City from an ideal vantage point—and learn insider facts and stories about the city's top attractions—on this Chicago River cruise. Travel in comfort aboard a boat equipped with both indoor and outdoor seating areas. Covering more than 130 years of architectural history, this tour is the perfect opportunity to see a huge area of the city without the hassle of taxis and public transit.

4.5

(1,544)

from $45

Chicago River 90-Minute Architecture Tour

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.

(9,961)

from $45

See Chicago's magnificent skyline at night!

Chicago By Night River and Lake Cruise

City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River

4.5

(310)

from $50

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.

4.6

(68)

from $85

City Cruises Chicago: Signature Lunch Cruise on Lake Michigan

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).

3.9

(354)

from $63

City Cruises Chicago: Fireworks Signature Dinner Cruise

2 to 3 hoursFree Cancellation

3.9

(85)

from $128

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

30 to 45 minutesFree Cancellation

4.4

(910)

from $33

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.

Chicago Architecture Center River Cruise aboard First Lady

1 hour 30 minutes

4.9

(5,842)

from $57

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

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.

5.0

from $57

Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

(568)

from $46

Chicago Lake and River Architecture Tour

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.

(2,330)

from $45

Historical and Architectural Chicago Fireboat River & Lake Cruise

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!

4.9

(271)

from $47

Chicago River Ghost & Dark History Night Cruise

Chicago 3D Fireworks Cruise

4.1

(113)

from $46

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.

4.2

(231)

from $52

City Cruises Chicago: Premier Lake Michigan Brunch Cruise

Get a fresher perspective on the Windy City—and a traffic-free one—with this Chicago River architecture cruise. As you pass by some of Chicago's most notable buildings, you'll dine on a 3-course lunch, listening to onboard narration about the city's architecture and history along the way. Unlike your standard walking tour, you can expect comfort, great food, and endless photo opportunities.

3.9

(28)

from $105

City Cruises Chicago: River Architectural Lunch Cruise

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.

4.3

(41)

from $74

Chicago Architectural River Cruise

Chicago River Sunday Funday Mimosa or Bloody Mary Party Cruise

(819)

from $50

1 hour 30 minutes

4.2

(27)

from $50

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!

Chicago Private Boat Tours

2 to 8 hoursFree Cancellation

4.4

(7)

from $299

Per group

Get a chance to experience the Windy City from multiple vantage points during this two-hour, small-group boat tour in Chicago. Hop aboard a secure and reliable US Navy-built Rigid Inflatable Boat (RIB) for a unique sightseeing experience. Pass by iconic sights such as Navy Pier, Soldier Field, Fort Dearborn, Vietnam Memorial, Wolf Point, Shedd Aquarium, and more, all while comfortably seated in a group capped at only six people.

Small-Group Sightseeing Boat Tour in Chicago

Set sail for a memorable experience on Lake Michigan with a Signature Chicago Brunch Cruise that is as scenic as it is delicious! You'll savor a chef-prepared buffet and bottomless mimosas while in our comfortable indoor areas. Marvel at unparalleled views of Chicago’s iconic landmarks, such as Willis Tower and Navy Pier from inside or enjoy fresh breezes on the open-air decks. This fun-filled brunch cruise experience for all ages is complete with lively DJ entertainment, dancing, games, and a fully stocked cash bar. Elevate your weekend plans with a one-of-a-kind brunch cruise on the water!

5.0

(95)

from $89

City Cruises Chicago: Signature Brunch Cruise on Lake Michigan

4.0

(4)

from $101

Soak up unbeatable views of Lake Michigan and the Chicago skyline—and stay on the water long enough to watch the lights come on in the city—on this private, sunset sailing tour. This charter is completely customizable, giving you the chance to choose your music, route, and up to five additional guests. Sail into the sunset with your own drinks and snacks (refrigerator and ice on board) and your family or friends by your side, all led by US Coast Guard–certified captain.

Serene Private Sunset Sail on Lake Michigan - Navy Pier, Chicago

Historical and Architectural Chicago Fireboat River & Lake Cruise

5.0

(27)

from $508

Per group

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What are people saying about Chicago

Richard_H, May 2026

A great tour on a piece of Chicago history

This was a very informative and fun tour. You got to ride on a real piece of Chicago history while learning about the the very diverse architecture of this city. I lived here as a kid/young adult never knew we had a lock between the river and the lake. 🤯. The tour guide was funny and knowledgeable. He answered all our questions and gave us lots of little gems. I learned some things on this tour that I had not heard of on other boat tours. They had a full bar with hot and cold drinks. Bartender was great and made good drinks. Two bathrooms on board. Was a very enjoyable experience. I would highly recommend this tour if you are looking to do a boat tour.

Chicago Architectural River Cruise

Heidi_W, Apr 2026

This is the best way to...

This is the best way to acclimate yourself to Chicago. We learned so much from the tour guide and used what we learned all weekend long. The crew was amazing and professional and the complementary drinks especially he hot chocolate was much needed on this cold afternoon.

City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River

chloe_b, Dec 2025

Thank you leslie <3

Leslie made our experience wonderful! We celebrated my girlfriend’s birthday by doing the brunch. Even though it was raining, it was still beautiful! Leslie made sure that our mimosas were filled, the staff was very friendly, and food was delicious. We will definitely be back for another brunch or dinner!

Chicago City Tour with Architecture River Cruise Option

Dawn_G, Dec 2025

Worth it!

Love all the information of the buildings’ history! Seeing them in one area was amazing! The tour took about an hour. I didn’t visit the bar/cocoa area downstairs but it’s great that they have one. The guide was funny and friendly. He interacted with us as well. Once trip was over, he stood by to say bye to everyone. I would do it again!

Chicago By Night River and Lake Cruise

Amanda_K, Nov 2025

Just do it!

Haley (aka Daisy the cow) was an amazing guide. Very knowledgeable about the architecture and history of Chicago. The tour is a must do!! You see Chicago in such a different way! Its absolutely stunning! Long enough to get your money's worth, but short enough it doesn't soak up alot of your vacay! Just do it!!

Small-Group Sightseeing Boat Tour in Chicago

Sian_S, Sep 2025

Outstanding Value

Fantastic trip for a very reasonable price. The host was friendly and knowledgeable and made the trip a real pleasure. We were delighted to find this trip also included the city river tour in the price. One very slight improvement would be to make the location a little better signposted but we would definitely book again.

Chicago CityPASS®

Jeremy_B, Sep 2025

City Pass Fun!

We had a blast! Willis Tower was really cool. Field Museum is massive, it takes a very long time to get through. The aquarium was a hit with everyone. The architecture boat ride was amazing! I wish I could remember it tour guides name. He had such a wealth of knowledge about all of the current, past, and future buildings and he was hilarious to boot. If you do it at sunset you get to see some pretty incredible views of the city. We ran out of time and weren’t able to do all 5 attractions.

City Cruises Chicago: River Architectural Lunch Cruise

Shaterra_S, Aug 2025

Directions were poor but the cruise was very nice.

I can confirm that the instructions were awful. The pin that is in the reservation is for another parking lot. I recommend you follow the instructions that Viator gives you to start and then heed mine. The directions will take you to a parking lot on North Colombus Drive. If you stop there, you will miss your reservation. Make that right at the light on N Columbus Drive and go uphill. At the top of the hill, the NBC building should be on your right. If see a draw bridge, DO NOT CROSS IT. When you made it to the top of the hill, cross the street and make another right. You are standing at a parking lot again which is on your left now and facing ahead is the university of Chicago building. Right in front of the building there are some flags, that is where you will find stairs that will take you down to the Odyssey. Your destination will be immediately on your right. As for the cruise, the food was great. The portions were not small and the service was great. It was very informative, lively and a perfect time to spend the afternoon. Will return in the future for a dinner cruise.