Top Chicago Sightseeing Cruises

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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).

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Lake Michigan Skyline Cruise in Chicago

30 to 45 minutesFree Cancellation

4.4

(948)

from $34

Likely to Sell Out

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

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.

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Chicago River 45-Minute Architecture Tour from Magnificent Mile

45 minutesFree Cancellation

4.7

(3,586)

from $28

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.

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Chicago Sightseeing River and Lake Cruise

1 hour 30 minutesFree Cancellation

4.7

(723)

from $46

Likely to Sell Out

This tour cruises the Chicago River and Lake Michigan.

Chicago Lake and River Architecture Tour

1 hour 30 minutesFree Cancellation

4.7

(2,438)

from $45

Likely to Sell Out

Explore Chicago's legendary architecture and history.

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.

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Chicago River 90-Minute Architecture Tour

1 hour 30 minutesFree Cancellation

4.7

(10,928)

from $45

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.

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Chicago Architecture River Cruise

1 hour to 1 hour 30 minutesFree Cancellation

4.8

(16,982)

from $39

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.

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Chicago Architecture Center River Cruise aboard First Lady

1 hour 30 minutes

4.9

(7,060)

from $57

Likely to Sell Out

360 panoramic views of the Chicago skyline at sunset.

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.

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Lake Michigan Sunset Cruise in Chicago

1 hour 30 minutesFree Cancellation

4.5

(1,688)

from $45

Likely to Sell Out

Chicago River 90-Minute Architecture Boat Tour

1 hour 30 minutesFree Cancellation

4.8

(1,889)

from $37

Chicago River Tiki Bar Party Cruise from Chicago River Wednesdays

1 hour 15 minutes

4.0

(128)

from $42

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.

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Chicago By Night River and Lake Cruise

1 hour 30 minutesFree Cancellation

4.5

(432)

from $50

Likely to Sell Out

Lake Michigan Fireworks Cruise in Chicago

2 to 3 hours

4.2

(142)

from $60

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.

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Chicago Architectural River Cruise

1 hour 30 minutesFree Cancellation

4.7

(859)

from $50

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.

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City Cruises Chicago: Signature Lunch Cruise on Lake Michigan

2 hoursFree Cancellation

4.0

(384)

from $63

Likely to Sell Out

City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River

2 hoursFree Cancellation

4.5

(81)

from $85

Small-Group Sightseeing Boat Tour in Chicago

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.

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Small-Group Sightseeing Boat Tour in Chicago

2 hoursFree Cancellation

5.0

(119)

from $89

Historical and Architectural Chicago Fireboat River & Lake 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.

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Historical and Architectural Chicago Fireboat River & Lake Cruise

2 hoursFree Cancellation

4.9

(483)

from $47

The Chicago River, as seen from our stop on wacky Wacker Drive

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.

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Chicago City Tour with Architecture River Cruise Option

2 to 4 hoursFree Cancellation

4.8

(735)

from $50

City Cruises Chicago: Premier Lake Michigan Brunch Cruise

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.

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City Cruises Chicago: Premier Lake Michigan Brunch Cruise

2 hoursFree Cancellation

3.9

(33)

from $105

Chicago Skyline Tiki Chic Party Cruise on Lake Michigan

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!

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Chicago Skyline Tiki Chic Party Cruise on Lake Michigan

1 hour 30 minutes

4.0

(36)

from $42

Chicago River Sunday Funday Mimosa or Bloody Mary Party Cruise

1 hour 30 minutes

4.3

(31)

from $42

Chicago Lake Michigan Skyline Sunday Funday Party Cruise

Enjoy a fun, festive, and one-of-a-kind way to admire the Chicago skyline and views over Lake Michigan aboard this tiki boat tour. Choose from several start times, meet your tiki-themed vessel right on the Chicago Riverwalk, and climb aboard. As you sail along the Chicago River and out onto Lake Michigan, you’ll enjoy a new perspective on the Windy City—and can purchase mimosas and other beverages at the on-board cash bar.

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Chicago Lake Michigan Skyline Sunday Funday Party Cruise

1 minute to 1 hour 30 minutes

4.5

(10)

from $42

Get the most out of your trip to Chicago as you enjoy discount access to five of the city’s top attractions with the CityPASS®. This easy-to-use mobile ticket grants you free entry into top-tier sights including the Chicago's most famous aquarium and Skydeck Chicago, plus your choice of admission to three of the following attractions: Field Museum, Art Institute of Chicago, Museum of Science and Industry, 360 CHICAGO Observation Deck, Adler Planetarium, or Shoreline Sightseeing Architecture River Tour.

from $144

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!

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City Cruises Chicago: Signature Brunch Cruise on Lake Michigan

2 hoursFree Cancellation

3.7

(9)

from $105

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Top Attractions in Chicago

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Chicago boasts some of the most spectacular views in the Midwest—from the glittering lakefront to the soaring skyscrapers that make up the city’s unmistakable skyline. And the best way to take in the views? Opt for a Chicago sightseeing cruise to experience it all. Book a seat on a Chicago River architecture tour, enjoy a private sail on Lake Michigan, or join a small-group tour that showcases the city’s most famous waterside sights.

Top Chicago Sightseeing Cruises

27 results

Top Attractions in Chicago

Chicago Riverwalk

The Magnificent Mile

Skydeck Chicago at Willis Tower (Sears Tower)

Chicago Theatre

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