Top Chicago On the Water - page 2

City Cruises Chicago: Premier Lake Michigan Brunch Cruise

Chicago dogs, deep-dish pizza, brownies, and craft beer are all sampled on this half-day bike tour through the Windy City. Cover about 13 miles (21 km), following your guide at a moderate pace through Chicago neighborhoods. On the day tour, ride through Wrigleyville, Old Town, Lincoln Park, and Gold Coast. On the night tour, visit Chicago’s Riverwalk, Millennium Park, Buckingham Fountain and the Lakefront Trail. As you go, stop for generous food and beer tasters.

3.9

(29)

from $105

From deep-dish to hot dogs, taste Chicago Classic Dishes on our Chicago Food & Bike Tour. Ride by Bicycle, learn the stories, and savor every stop on the best Food & Bike Tour in Chicago.

Chicago Bike & Classic Food Tour: Bikes, Bites & Views - Adults

4 hours 30 minutesFree Cancellation

(754)

from $89

Chicago Crime and Mob Bus Tour

1 hour 30 minutes to 2 hoursFree Cancellation

4.6

(3,401)

from $49

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

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

(2,165)

from $85

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.

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

Chicago City Tour with Architecture River Cruise Option

2 to 4 hoursFree Cancellation

4.8

(728)

from $50

Chicago Water Taxi River Fireworks Cruise

45 minutesFree Cancellation

4.5

(11)

from $25

Private Lake Michigan Sailing Charter with Skyline Views

A private sailing charter on Lake Michigan offers a serene escape with stunning skyline views of Chicago. Departing from Montrose Harbor, enjoy a relaxed atmosphere ideal for families, couples, or casual groups looking for a break from city life. Experience the charm of a personal sailing trip as you glide across the water, capturing perfect moments of the skyline from your private vessel. This charter caters to visitors and locals alike, providing a unique perspective of the city while ensuring a peaceful outing on the lake. - Private sailboat reserved exclusively for your group - BYOB-friendly with restroom and cooler space onboard - Scenic views of the Chicago skyline and lakefront - Ideal for families, groups, couples, and first-time sailors

Private Lake Michigan Sailing Charter with Skyline Views

3 hoursFree Cancellation

4.5

from $1,150

Per group

City Cruises Chicago: Fireworks Premier Plus Dinner Cruise

Enjoy a celebratory way to sightsee—and a river cruise like no other—with this evening excursion along the Chicago River. Your modern, glass-enclosed boat makes for a comfortable ride, no matter the weather—and gives panoramic views of Chicago’s well-known architectural gems. As you go, indulge in a gourmet, multi-course meal while enjoying live entertainment, including a DJ and fireworks displays on Wednesdays and Saturdays.

City Cruises Chicago: Fireworks Premier Plus Dinner Cruise

2 to 3 hoursFree Cancellation

4.0

(6)

from $169

Chicago River Tiki Bar Party Cruise from Chicago Riverwalk

1 hour 15 minutes

4.0

(118)

from $42

Chicago River Sunday Funday Mimosa or Bloody Mary Party Cruise

1 hour 30 minutes

4.3

(30)

from $50

City Cruises Chicago: Fireworks Signature Dinner Cruise

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).

City Cruises Chicago: Fireworks Signature Dinner Cruise

2 to 3 hoursFree Cancellation

3.9

(91)

from $128

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

Chicago Fireboat Fireworks Cruise

1 hour 30 minutesFree Cancellation

(9)

from $57

Enjoy a fun and scenic 90-minute Cycleboat Cruise along the beautiful Chicago River! Take in stunning skyline views as you pedal, relax, and sip your favorite drinks with friends, family, or that special someone. • 1.5-hour cruise up and down the iconic Chicago River • Comfortable boat with 10 cycle stations and bench seating at the front • Maximum capacity of 16 passengers — perfect for smaller groups or couples • BYOB! Bring your own beverages and snacks to enjoy onboard • Departs from the Water Plaza on the Chicago Riverwalk (between Wells Street and LaSalle Street bridges) Whether you want a lively group outing or a relaxing ride through the city, this Cycleboat Cruise is one of the most unique ways to see Chicago from the water — no full-boat rental required!

Chicago River Cycleboat Cruise

1 hour 30 minutesFree Cancellation

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.

(10)

from $65

City Cruises Chicago: River Architectural Lunch Cruise

City Cruises Chicago: River Architectural Lunch Cruise

On A Boat Sailing offers an all-inclusive, private VIP sailing experience departing from the brand-new Navy Pier Marina in Downtown Chicago. If you appreciate attention to detail, hospitality, and sophisticated service, this is the boat rental for you! Amenities on board include: Pricing for private groups up to 7 guests. Custom pricing available for larger groups up to 12. Anchoring in the Chicago Playpen for swim and float parties. Swim platform with rinse shower-lily pad, noodles, life-jackets and floaties. Large open cockpit seating area. Complimentary beverages and snacks or BYO (alcohol allowed). Stereo surround sound speakers with Bluetooth connection. Fridge with ice, fully stocked kitchenware. Skyline views of Downtown Chicago, Navy Pier and the Chicago Lighthouse. Anchoring for concerts at Northerly Island. Kitchen, bathroom and changing room on board.

4.3

(42)

from $74

Navy Pier Chicago: Private Sailboat Charter with Captain

Navy Pier Chicago: Private Sailboat Charter with Captain

3 hoursFree Cancellation

from $1,099

Per group

Monday Night Concert Series: Blues and Views Aboard Tall Ship

Chase away your Monday blues with Chicago’s coolest concert at sea! Hop aboard the historic Tall Ship Windy for a 2-hour live blues music cruise on Lake Michigan, featuring city skyline views and a rotating roster of top local and international artists. With a full-service bar and plenty of space to move, relax, and dance, this floating music event blends unbeatable atmosphere with legendary sounds—perfect for date nights, group outings, or music lovers looking for a summer highlight. VIP boarding upgrades and kid discounts available. Book early; these shows sell out fast!

Monday Night Concert Series: Blues and Views Aboard Tall Ship

2 hours

Sample some of the Windy City's tastiest donuts—and head to locals-loved dessert destinations that most visitors miss—on this one-of-a-kind walking tour. With your guide in the lead, head to a number of Chicago’s tastiest donut bakeries, all while exploring the city's vibrant downtown Loop neighborhood. All tastings are included in the tour cost, and vegan, gluten-, and nut-free options are also available upon request.

(1)

from $81

Chicago's Downtown Donut & Family-Friendly History Walking Tour

Chicago's Downtown Donut & Family-Friendly History Walking Tour

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!

(1,459)

from $70

City Cruises Chicago: Signature Brunch Cruise on Lake Michigan

City Cruises Chicago: Signature Brunch Cruise on Lake Michigan

3.3

(7)

from $94

Get ready for the most complete adventure the city has to offer—an immersive Full Day Chicago Food Tour and Walking Tour that blends Chicago’s legendary flavors with its most iconic landmarks. Savor Chicago Pizza, Hot Dogs, Italian Beef, Garrett’s Chicago Mix Popcorn, and the original Palmer House Brownie, or elevate your day with our VIP craft beer upgrade. This unforgettable Chicago in a Day Tour explores Millennium Park, the Chicago Riverwalk, Michigan Avenue, Cloud Gate, Chicago Theater, and more, guided by true local experts. Enjoy a 5-hour journey through culture and cuisine, plus a FREE 2-hour bike or kayak rental to continue the adventure along Lake Michigan. Recently honored among the “Top 10 Food Tours in America” (USA Today) and “Top 20 Food Tours in the World” (TripAdvisor), this award-winning Culinary Tour is one of the top Things to do in Chicago. Don’t miss the most delicious, scenic Full Day Food Tour in Chicago—all in one extraordinary day.

A Chicago hot dog loaded with bold, colorful toppings is one of the tastiest Things to do in Chicago. Our Chicago Food Tours feature this classic bite, making Food Tours in Chicago unforgettable.

Chicago Full-Day Walking Food Tour with Free Bike or Kayak Rental

5 hoursFree Cancellation

Delve into the world of natural history with admission to Chicago’s Field Museum. Choose general admission or upgrade to visit one or more special exhibits. Spend as long as you like exploring the museum's extensive collection of artifacts. Get to know SUE, the world's largest T. Rex, or stroll through the sparkling Hall of Gems. Also take advantage of daily tours led by knowledgeable Field Museum docents, free with admission.

(2)

from $99

Field Museum of Natural History Admission Tickets

4 hoursFree Cancellation

4.6

(545)

from $29

S. Silvera Charters offers a unique luxury yacht rental for those looking to create unforgettable memories on the water. Perfect for special events or leisurely cruising, this charter allows you to set your own schedule and enjoy a personalized experience. With a minimum rental of three hours, you can relax on board while exploring beautiful coastal views. Captain's fees are separate, ensuring a tailored experience for your group. - Exclusive yacht rental for luxury experiences - Flexible scheduling with afternoon and evening options - Minimum three-hour rental for ample exploration - Personalized service with optional captain at an additional fee

Chicago Private Rental Yacht Charter

3 to 8 hoursFree Cancellation

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.

(1)

from $1,300

Per group

Chicago's Fireworks Show aboard Tall Ship Windy!

Chicago's Fireworks Show aboard Tall Ship Windy!

1 hour 30 minutes

4.7

(18)

from $114

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.

Chicago Lake Michigan Skyline Sunday Funday Party Cruise

1 minute to 1 hour 30 minutes

4.2

(6)

from $42

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Top Attractions in Chicago

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Attractions

What are people saying about Chicago

Chicago's Lake Michigan Downtown Kayak Rental at Ohio Street Beach

alyssa_l, May 2026

Fun daytime activity in Chicago!

A fun activity for a beautiful Chicago day! The guide who greeted us was so friendly and helpful. He gave us great instructions, locked up my bag for when we were on the water, and got us all set up to go. The wind made the water a little choppy but it’s to be expected. The water color was gorgeous. Highly recommend!

Chicago's Downtown Donut & Family-Friendly History Walking Tour

kberteaux, May 2026

No notes

Super great introduction to several amazing downtown bakeries. My favorite was the Tahitian vanilla donut at Firecakes, followed by the red velvet at Dan's. There were PLENTY of donuts and I left happy and fully sugared out. This covers a lot of over a mile of walking, FYI. And it ended exactly on time which I always appreciate.

Chicago Bike & Classic Food Tour: Bikes, Bites & Views - Adults

Darcy_S, May 2026

Great food, great guide, great biking

This was an awesome tour. Matt was our guide and it was his first solo tour and he did a great job. Go hungry! This is not “tastes” of food, it is a full on meal by the end of the day. The biking was easy, you are on some city streets, Matt had everything under control and we felt safe the whole time. I would highly recommend this tour.

Field Museum of Natural History Admission Tickets

Heather_T, Feb 2026

Highly recommend!

Wow-what an incredible museum! I spent hours exploring! Highly recommend if you’re interested in earth’s history! So much to discover about plants, animals, and people. SUE is extraordinary! The ticket was super easy to purchase and I walked right in upon arrival. Overall, a fantastic experience!

City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River

chloe_b, Dec 2025

Thank you leslie <3

Leslie made our experience wonderful! We celebrated my girlfriend’s birthday by doing the brunch. Even though it was raining, it was still beautiful! Leslie made sure that our mimosas were filled, the staff was very friendly, and food was delicious. We will definitely be back for another brunch or dinner!

Chicago Seadog River & Lake Architectural Tour

Steve_S, Sep 2025

Ryan and his entire team...

Ryan and his entire team were fantastic. They provided fun and engaging tour also allowing time for questions. We highly recommend attending this tour. It is suitable for all ages and especially fun for those who are interested in learning about the architecture of the downtown area.

Small-Group Sightseeing Boat Tour in Chicago

Matthew_P, Aug 2025

Perfect ending to a great family trip to Chicgao!

This was an absolute awesome experience! Highly knowlegable and friendly captian! Good mix of excitement and information. Perfect for a family! Way better than one of those crowded commercial river tours...our captain previously worked for one of those and had extensive knowledge! 1000x recommend!