Top Chicago Cruises &amp; Sailing

Chicago River 45-Minute Architecture Tour from Magnificent Mile

45 minutesFree Cancellation

(3,305)

from $28

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.

Explore Chicago's legendary architecture and history.

Chicago River 90-Minute Architecture Tour

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.

(10,255)

from $45

Chicago Architecture River Cruise

1 hour to 1 hour 30 minutesFree Cancellation

(16,334)

from $39

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.

Lake Michigan Sunset Cruise in Chicago

(1,591)

from $45

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.

City Cruises Chicago: Signature Lunch Cruise on Lake Michigan

City Cruises Chicago: Signature Lunch Cruise on Lake Michigan

Chicago 3D Fireworks Cruise

3.9

(362)

from $63

See Chicago's magnificent skyline at night!

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.

4.2

(241)

from $52

Chicago By Night River and Lake Cruise

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.

(337)

from $50

Chicago Architecture Center River Cruise aboard First Lady

Chicago Architecture Center River Cruise aboard First Lady

1 hour 30 minutes

4.9

(6,221)

from $57

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

(922)

from $33

Chicago River 90-Minute Architecture Boat Tour

(1,700)

from $37

Lake Michigan Fireworks Cruise in Chicago

2 to 3 hours

4.2

(130)

from $55

Skyline Queen showcasing the Chicago Skyline!

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.

Chicago Sightseeing River and Lake Cruise

(604)

from $46

Chicago Water Taxi River Fireworks Cruise

45 minutesFree Cancellation

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).

(11)

from $25

City Cruises Chicago: Fireworks Signature Dinner Cruise

City Cruises Chicago: Fireworks Signature Dinner Cruise

2 to 3 hoursFree Cancellation

3.9

(90)

from $128

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

1 hour 15 minutes

(22)

from $91

Admire a side of Chicago that few other visitors get to experience—and enjoy a relaxing trip out on the water, tailored to your party—with this private sailboat charter and sailing tour. You and up to five other guests will have the exclusive use of a sailboat, complete with a captain for the duration of your tour. Sail on Lake Michigan and enjoy the sights of Chicago’s striking skyline. If you want, you can even take a turn at the helm.

Heading out to Four Mile Crib on a beautiful day of sailing.

Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago

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.

5.0

(70)

from $567

Per group

Historical and Architectural Chicago Fireboat River & Lake Cruise

Historical and Architectural Chicago Fireboat River & Lake Cruise

4.9

(337)

from $47

Chicago Lake and River Architecture Tour

This tour cruises the Chicago River and Lake Michigan.

(2,348)

from $45

City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River

Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seats in town! Grab a cool drink from our full bar, relax, and enjoy a leisurely evening sail past the brilliant and beautiful Chicago nighttime skyline. Windy provides the accompanying sound track, over the ship sound system coordinated fireworks display, amazing show! Rain or Shine event. no umbrellas are allowed to be opened underway. Tall Ship Windy, located on Navy Pier, and we have a ticket booth and dock, in front of the Billy Goat Bar and Grill. Arrive early, as fireworks crowds are huge! expect travel delays.

(75)

from $85

Chicago's Fireworks Show aboard Tall Ship Windy!

Chicago's Fireworks Show aboard Tall Ship Windy!

1 hour 30 minutes

4.6

(16)

from $114

Chicago River Ghost & Dark History Night 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!

Chicago River Ghost & Dark History Night Cruise

Chicago River Floating Tiki Bar Cruise Friday & Saturday

4.1

(132)

from $46

1 hour 15 minutes

5.0

(4)

from $42

City Cruises Chicago: Signature Brunch Cruise on Lake Michigan

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!

City Cruises Chicago: Signature Brunch Cruise on Lake Michigan

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

3.5

(6)

from $101

Chicago Fireboat Fireworks Cruise

Chicago Architecture Center River Cruise aboard First Lady

(6)

from $57

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Top Attractions in Chicago

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What are people saying about Chicago

Patricia_M, Jun 2026

Amazing adventure on the river

Amazing trip through the history of Chicago architecture and the river. Our guide, Phil, told amazing stories of buildings, builders, architects, and historical events. Truly a remarkable adventure through time. Great ship, staff, captains and crew. We all loved the trip. Thank you!

Chicago Sightseeing River and Lake Cruise

Heather_M, Jun 2026

Just enough info to keep...

Just enough info to keep things interesting/not boring. Boat was clean and comfortable, great guide. Staff at the dock friendly and helpful. BE WARNED: you have to go through a lock to get out to the lake. It can get backed up. We ran about 45 min late. Just keep in mind for dinner/show reservations.

Lake Michigan Skyline Cruise in Chicago

Andrea_D, Jun 2026

I misjudged my timing...

I misjudged my timing with my Uber and arrived late for my booking. Staff easily rescheduled it with no charge. It was an enjoyable way to spend 45 minutes before heading back to the airport. I had my travel bags with me, and there was plenty of room.

Lake Michigan Sunset Cruise in Chicago

Candy_T, Jun 2026

Great views! Do not miss!

What a great experience! This sunset cruise was fab and it was so fun seeing how the lock works for the river and the lake. The cruise went a little long due to some other boats and the lock system but all in all, it was wonderful. Highly recommend and would do it again.

Historical and Architectural Chicago Fireboat River & Lake Cruise

Jenny_B, Jun 2026

Fireboat river and lake tour.

Fantastic tour. Informative and it took in a lock between river to lake. One of the only tours that did both. The guys on our cruise obviously loved their job and had plenty of knowledge of the architecture and history and told it in an interesting and fun way. The old fire boat had plenty of history too.

Chicago By Night River and Lake Cruise

Fatmata_B, May 2026

The trip was good sight...

The trip was good sight seeing was great. Tour guide was good made a lot of jokes. It was fun, but for me all they had was alcohol so water for free will all have been nice instead of only getting alcohol for free. And the regular boarding line is so long and we delayed for almost 25 minutes before we started our tour.

City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River

Fatmata_B, May 2026

The Trip was great. Good...

The Trip was great. Good ambience, Trish was exceptional she made us feel welcome and very comfortable. The food was great and the scenery is spectacular if you need to take pictures. The Dj on board was great he played good music and also his tour guide was great. This trip is definitely worth it.

Chicago Lake and River Architecture Tour

Nathan_C, Oct 2025

Excellent very happy

Visiting Chicago from Ireland for first time with friends and this was an excellent way to kick off the holiday. Gives you good view of Chicago, learn a bit of history from your guide, indoors available if it’s cold. Overall perfect and price was perfect too very happy with it. Drinks were available on board but I didn’t like the coffee however you could just bring coffee with you on board from somewhere near by. Overall excellent experience.

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.

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.

Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago

Kira_M, Jul 2025

Best Part of Our Trip

We took a two hour sail for our daughter’s 24th birthday. It was fantastic! Everyone in the family felt like it was the best part of our vacation. Captain Mike was awesome and answered all kinds of questions about sailing and some Chicago history. I cannot recommend this enough!