Top Chicago Cruises &amp; Sailing

Chicago River 45-Minute Architecture Tour from Magnificent Mile

45 minutesFree Cancellation

(3,392)

from $28

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

(1,618)

from $45

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

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.

(10,470)

from $45

See Chicago's magnificent skyline at night!

Chicago By Night River and Lake Cruise

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.

(384)

from $50

Chicago Architecture River Cruise

1 hour to 1 hour 30 minutesFree Cancellation

4.8

(16,557)

from $39

Chicago 3D Fireworks Cruise

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).

4.2

(252)

from $52

Lake Michigan Skyline Cruise in Chicago

30 to 45 minutesFree Cancellation

4.4

(933)

from $34

City Cruises Chicago: Signature Lunch Cruise on Lake Michigan

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

3.9

(371)

from $63

Lake Michigan Fireworks Cruise in Chicago

2 to 3 hours

4.2

(131)

from $55

Chicago Architecture Center River Cruise aboard First Lady

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

(6,451)

from $57

Chicago River 90-Minute Architecture Boat Tour

4.8

(1,808)

from $37

Chicago Lake and River Architecture Tour

This tour cruises the Chicago River and Lake Michigan.

(2,373)

from $45

City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River

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.

(79)

from $85

Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and 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!

(643)

from $46

Chicago River Ghost & Dark History Night Cruise

Chicago River Ghost & Dark History Night Cruise

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.

4.1

(160)

from $46

Historical and Architectural Chicago Fireboat River & Lake Cruise

Historical and Architectural Chicago Fireboat River & Lake Cruise

4.9

(386)

from $47

Chicago Water Taxi River Fireworks Cruise

45 minutesFree Cancellation

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.

(12)

from $25

Small-Group Sightseeing Boat Tour in Chicago

Small-Group Sightseeing Boat Tour in Chicago

5.0

(104)

from $89

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.

City Cruises Chicago: River Architectural Lunch Cruise

City Cruises Chicago: River Architectural Lunch Cruise

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

4.3

(43)

from $74

1 hour 15 minutes

4.8

(24)

from $91

Chicago's Fireworks Show aboard Tall Ship Windy!

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.

Chicago's Fireworks Show aboard Tall Ship Windy!

1 hour 30 minutes

4.6

(21)

from $114

Chicago River Floating Tiki Bar Cruise Friday & Saturday

1 hour 15 minutes

5.0

(4)

from $42

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

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.

5.0

(70)

from $508

Per group

City Cruises Chicago: Premier Lake Michigan Brunch Cruise

City Cruises Chicago: Premier Lake Michigan Brunch Cruise

Historical and Architectural Chicago Fireboat River & Lake Cruise

3.8

(30)

from $105

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Top Attractions in Chicago

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What are people saying about Chicago

Carmen_L, Jul 2026

Wonderful Part of Chicago

This is a really cool experience and part of Chicago history! To actually see the history of the fire boat and the launching of it, along with the patches down below was amazing! I absolutely loved my entire experience. The crew members are very knowledgeable, and friendly. I would definitely take this tour with them again.

Chicago By Night River and Lake Cruise

Gabrielle_B, Jul 2026

Pleasant Suprise!

This was a wonderful experience. We chose the First Lady as a last‑minute excursion to close out our vacation, and it ended up being a highlight of our trip. The crew was friendly, professional, and exceptionally knowledgeable.I highly recommend taking the evening tour being out on the lake and river while the city lights reflect off the architecture creates an unforgettable atmosphere. It’s the perfect blend of learning about Chicago’s rich history and enjoying a relaxing, scenic experience.The gentleman leading the tour did an excellent job balancing insightful information with moments for us to take photos and simply enjoy the view, ensuring we never missed anything important.We can’t wait to do this again on our next visit. Well done 😊

Chicago CityPASS®

Dana_R, Jul 2026

Loved the City pass and...

Loved the City pass and the expedited lines that allowed us to make the most of our time in Chicago (no waiting in long lines). We had 5 days to see the sites and were able to plan all of our activities before we even arrived in Chicago. We stayed at the Sheraton Grand Riverwalk near Navy Pier over July 4th weekend.

Small-Group Sightseeing Boat Tour in Chicago

Carolina_M, Jul 2026

Thrilling and Beautiful

Thrilling and beautiful suitable for all ages Shows off Chicago and her history. Captain Ken has a charming personality and a great knowledge of Chicago. It is a little difficult to find but despite us being late he gave us the full tour. We would do this trip again if in Chicago PS When you reach the harbour Captain Ken can be found at Peir A

Lake Michigan Sunset Cruise in Chicago

Michelle_B, Jun 2026

Great views and a surprise on our tour!

Even the rain didn't dampen the experience. I chose this as our first tour in Chicago and of course it decided to rain most of the day. I almost considered cancelling this one but since it was non-refundable, we gave it a go. I am glad we did. There are interior areas on the boat so we were able to stay dry. The tour starts on the Chicago River and goes through the lock to get to Lake Michigan. The lake was choppy but the boat handles the waves fine and they moved to a calmer area so we could enjoy the Chicago Skyline from the lake. Had it not rained, we would have been able to see a fireworks show as well, but the lit up skyline was the real highlight of the tour. That is, until our new friends sitting at our table allowed us to witness their marriage proposal. She said "yes." Even without the proposal, and with all the rain, the tour was fun a gave us views of Chicago you just can't get on the shore.

Chicago Sightseeing River and Lake Cruise

REGINA_E, Jun 2026

Good choice for cruise

River cruise into Lake Michigan with an amazing guide who knew the entire history of Chicago. He points out a lot of buildings and other sights. Before you can go into the lake you have to wait for the water to settle which is interesting in itself. You will have a great view of Chicago from the water.

Chicago Architectural River Cruise

Amy_P, Jun 2026

Worth it, honestly.

This boat tour was excellent (and I’ve done a couple in Chicago) staff was pleasant, free soft drinks and lemonade, seating was good. We came very close to leaving time and sat on the side of the boat and was still great. Our tour guide Lynn was extremely knowledgeable and her voice was very pleasant. I would 100% do it again.

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 River 90-Minute Architecture Boat Tour

Sophia_S, May 2026

THIS is the tour.

I have been on 4+ Chicago Architecture boat tours in my life and this one, with Hillary, was by FAR the best. She knows the city like the back of her hand (literally) and it was the quickest 90 min tour in the best way. Hillary deserves her own stand up comedy Netflix special. My whole family was so impressed and for the price, this was immaculate. I could not recommend this tour enough and if I would recommend a tour to a friend, this would be it! 1000/10!

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!