Top Chicago Dinner Cruises

15 results

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).

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3.9

(85)

City Cruises Chicago: Fireworks Signature Dinner Cruise

2 to 3 hoursFree Cancellation

from $116

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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4.7

(3,112)

Chicago River 45-Minute Architecture Tour from Magnificent Mile

45 minutesFree Cancellation

from $28

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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3.9

(348)

City Cruises Chicago: Signature Lunch Cruise on Lake Michigan

2 hoursFree Cancellation

from $63

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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4.8

(15,932)

Chicago Architecture River Cruise

1 hour to 1 hour 30 minutesFree Cancellation

from $39

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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4.7

(9,835)

Chicago River 90-Minute Architecture Tour

1 hour 30 minutesFree Cancellation

from $45

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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4.4

(906)

Lake Michigan Skyline Cruise in Chicago

30 to 45 minutesFree Cancellation

from $33

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.

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4.3

(40)

City Cruises Chicago: River Architectural Lunch Cruise

2 hoursFree Cancellation

from $74

Visit the Skydeck, located on the 103rd floor of the Willis Tower (formerly the Sears Tower), with ease thanks to this prebooked ticket option. Avoid long lines at the ticket office and enter directly to access the highest point in Chicago. Peruse interactive displays and exhibits showcasing Chicago's history. Then walk out on to the Ledge, a glass balcony that offers unimpeded views of Navy Pier and Wrigley Field.

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4.3

(1,811)

Skydeck - Willis Tower Admission

30 minutes to 1 hour 30 minutesFree Cancellation

from $44

Discover the hidden gems of Chicago’s Loop area on a walking tour that showcases the best of the neighborhood’s stunning interiors and architectural must-sees. Step behind the facades to explore beautifully designed interiors—from art deco spaces to stained glass mosaics—as you follow a carefully curated route led by a guide. Along the way, learn about the city’s architecture, art, and history, and experience a side of Chicago often missed by travelers, all from a local’s perspective.

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5.0

(1,569)

Original Chicago Architecture Interiors Tour: Dazzling Interiors

2 hoursFree Cancellation

from $35

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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4.9

(5,690)

Chicago Architecture Center River Cruise aboard First Lady

1 hour 30 minutes

from $57

Likely to Sell Out

4.7

(2,315)

Chicago Lake and River Architecture Tour

1 hour 30 minutesFree Cancellation

from $45

Taste deep-dish pizza, a Chicago-style hot dog, Italian beef, Garrett’s popcorn & the original 1893 brownie on our top-rated Chicago Food Tours—the ultimate Chicago Culinary Tour experience!

Eat your way through downtown Chicago on a walking food tour. Visit Millennium Park, the Palmer House Hotel, and other city landmarks and taste quintessential Chicago foods such as deep-dish pizza, hot dogs, and chocolate brownies. All food tastings are included, and the tour covers an easy 1.5 miles (2.4 km) suitable for most fitness levels. A bike or kayak rental is also included in the tour cost.

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4.9

(2,029)

Chicago Favorites Ultimate Food and Walking Tour

3 hoursFree Cancellation

from $85

Likely to Sell Out

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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4.8

(713)

Chicago City Tour with Architecture River Cruise Option

2 to 4 hoursFree Cancellation

from $50

A picture of Chicago Chinatown’s landscape shows vibrant streets, iconic arches, and rich culture—everything guests explore on our Chinatown Food Tours. Food Tours in Chinatown bring it all to life.

Immerse yourself in one of Chicago's most vibrant neighborhoods—and head off the tourist trail to discover sights and bites many visitors miss—on this small-group Chinatown food and walking tour. With your guide in the lead, learn about the cuisine of different regions of China, and discover the history of Chicago's Chinatown. Along the way, enjoy a generous array of tastings, from dim sum to Sichuan cuisine and beyond.

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4.9

(640)

Chicago's Chinatown Food and Walking Tour

3 hoursFree Cancellation

from $80

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.

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4.1

(334)

Lake Michigan 30-Minute Speedboat Ride

30 minutesFree Cancellation

from $31

Top Attractions in Chicago

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Attractions

What are people saying about Chicago

Chicago's Chinatown Food and Walking Tour

elizzadizon1012, Apr 2026

Great Chinatown food tour

Had an amazing time on this Chinatown food tour! Alex was incredibly knowledgeable—not just about the food, but also the rich history behind the neighborhood and each dish we tried. It made the whole experience so much more meaningful. I’d definitely recommend this tour to any foodie who loves exploring culture through cuisine. Such a great mix of learning and eating!

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Chicago Favorites Ultimate Food and Walking Tour

Marsha_M, Apr 2026

5 STARS ASK FOR MICKY. Great entertainment

This food tour is more than just eating! Micky is a top notch guide and you learn the history and legends about Chicago. All the Food was fantastic! There are just enough places that you don't get too much. The nice walk around after each stop was timed well. The entire tour was entertaining. Ask for Micky as your guide.

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Chicago Crime and Mob Bus Tour

Danielle_K, Jan 2026

A fun tour

My boyfriend and I were visiting Chicago and decided to do the Crime and Mob Boss tour. Our guide, Dane, was a bit goofy and playing the showman, but it was still very educative. The small pamphlets he handed out at the beginning also helped. We got to see in daylight the parking lot that was the site of the St. Valentine's Day Massacre. (Yes, there was duplication between the tours, but I don't mind.) You stop at the Biograph Theatre, where John Dillinger was killed, and you can take photos of a mural dedicated to him. One of the Harry Caray Steakhouse locations has a mini mob museum that is a stop. You get to hear about Leopold and Loeb, two young men who decided to commit a murder for fun. It's more grim history of Chicago. I had a great time and definitely recommend it.

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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!

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What Chicago lacks in mountains, it more than makes up for with water. The city is built on the southwestern shore of Lake Michigan and has the Chicago River running through it. For that reason, Chicago dinner cruises are a rite of passage. Enjoy a seated multiple-course meal or an all-you-can-eat buffet while passing some of Chi-Town’s most famous sites, including Navy Pier and the Willis Tower. Many cruises include alcoholic beverages and provide a live DJ. Some cruises even culminate with a fireworks display.

Top Chicago Dinner Cruises

15 results

Top Attractions in Chicago

The Magnificent Mile

Chicago Theatre

Skydeck Chicago at Willis Tower (Sears Tower)

Chicago River

Chicago Riverwalk

Art Institute of Chicago

The Magnificent Mile

Chicago Theatre

Skydeck Chicago at Willis Tower (Sears Tower)

Chicago River

Chicago Riverwalk

Art Institute of Chicago

The Magnificent Mile

Chicago Theatre

Skydeck Chicago at Willis Tower (Sears Tower)

Chicago River

What are people saying about Chicago

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