Top Chicago Dinner Cruises

City Cruises Chicago: Fireworks Signature Dinner Cruise

2 to 3 hoursFree Cancellation

3.9

(90)

from $128

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

2 hoursFree Cancellation

4.0

(363)

from $63

City Cruises Chicago: River Architectural Lunch 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.

City Cruises Chicago: River Architectural Lunch Cruise

2 hoursFree Cancellation

4.3

(42)

from $74

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

4.7

(3,323)

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

1 hour 30 minutesFree Cancellation

4.7

(10,294)

from $45

Chicago Lake and River Architecture Tour

This tour cruises the Chicago River and Lake Michigan.

1 hour 30 minutesFree Cancellation

4.7

(2,351)

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.

Chicago Architecture River Cruise

1 hour to 1 hour 30 minutesFree Cancellation

4.8

(16,383)

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.

Chicago Architecture Center River Cruise aboard First Lady

1 hour 30 minutes

4.9

(6,262)

from $57

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.

Chicago's Chinatown Food and Walking Tour

3 hoursFree Cancellation

4.9

(724)

from $80

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

(927)

from $33

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.

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!

Chicago Favorites Ultimate Food and Walking Tour

3 hoursFree Cancellation

4.9

(2,148)

from $85

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.

Skydeck - Willis Tower Admission

30 minutes to 1 hour 30 minutesFree Cancellation

4.3

(1,854)

from $44

Chicago Sunset Tour by Open-Top Bus with Live Guide

1 hour 30 minutesFree Cancellation

4.1

(175)

from $39

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.

Lake Michigan 30-Minute Speedboat Ride

30 minutesFree Cancellation

4.1

(346)

from $36

Top Attractions in Chicago

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What are people saying about Chicago

Chicago Favorites Ultimate Food and Walking Tour

Yolanda_M, Jun 2026

You’ll be full!

I have a big appetite and thought the portions would not fill me up for dinner. However, I was wrong! We had a full slice of Gino’s Chicago style pizza, a Chicago dog, a small slice of an Italian sandwich with A LOT of meat and a donut. Most of the food was good. I didn’t care for the hot dog from Mister J’s and I have had better from other restaurants/vendors. The tour company does recommend that you bring a water bottle and you should. Some places do give you a cup of water. I did enjoy the 1 1/2 mile tour with Elizabeth as our guide. She was very attentive and informative.

Original Chicago Architecture Interiors Tour: Dazzling Interiors

Michelle_B, Jun 2026

Interior Architecture Tour in the Loop.

Our guide, Heath, was enthusiastic and extremely knowledgeable about the architecture and the arts in Chicago. We enjoyed his story telling and saw places I would have been unaware of if I had not taken the tour. The tour covered many blocks in the Loop but was an easy walk for anyone in relatively good health. I will definitely be recommending the tour to my travel clients, family, and friends. And when Heath tells you to check out the dome NOT on the TOUR in the The Cultural Building, make sure you follow his advice. It was absolutely stunning.

Chicago's Chinatown Food and Walking Tour

Betsy_S, Jun 2026

I loved this tour.

Our guide, York was fantastic! Extremely knowledgeable in the history of Chinatown as well as Chicago in general. The food was great and I was happily surprised by the portion sizes. You won’t leave hungry, that is for sure. Great experience. Leave yourself enough time to explore more of Chinatown on your own once the tour is through. Highly recommend this tour!

Lake Michigan Skyline Cruise in Chicago

Felicia_M, May 2026

Chicago trip for granddaughter and her boyfriend.

We had a great time. Got there early for our trip, and they allowed us to get on an earlier boat. If it is windy as it was for us, make sure you have a jacket. If wearing shorts a blanket. That was on us. We did have jackets, but my legs definitely got cold.

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!