We Found These Experiences For You (28)
Boat Tour and Illinois
Sea Ray 450 Believe Chicago
For all ages • 3 to 8 hour options • Fully inspected yacht with special weekday pricing!
At Believe Tours Charter Chicago, we offer the ultimate yachting experience on our luxurious Sea Ray 50 ft! The yacht comes equipped with a spacious living area, full kitchen, two bathrooms, and a comfy bedroom. Our experienced team of professionals goes above and beyond to ensure you and your guests ...
Chicago
3 to 8 hour options
Boat Rental, Boat Tour
Believe Chicago
Copy to Clipboard to Share
Lakefront Sightseeing
Chicago’s most iconic lakefront landmarks, all in one scenic cruise!
Take in Chicago from the water on a relaxed lakefront cruise that showcases the city from every angle. Glide past the historic Chicago Lighthouse, built in 1893, before cruising along Navy Pier—home to the grand ballroom, Sable Hotel, the largest rooftop bar, and the iconic Ferris wheel. Continue through ...
Chicago
1+ Hours
Boat Tour
Chicago Blue Water Charters
Copy to Clipboard to Share
Sunset Tour
Watch the sun melt into the horizon on a peaceful offshore Chicago sunset cruise!
Ease out onto open water and watch Chicago fade into silhouette as the sun sinks low on the horizon. About two miles offshore, the sky opens up for a front-row view of a stunning sunset—and if timing and luck are on your side, you might even catch the rare green flash. It’s a calm, unforgettable ...
Chicago
1+ Hours
Boat Tour
Chicago Blue Water Charters
Copy to Clipboard to Share
Fireworks Tour
Watch Navy Pier fireworks from the best seat on the water!
Skip the crowds and take in Chicago’s fireworks from the best seat in the city—out on the water. Cruise just offshore from Navy Pier and watch the sky light up in a full, unobstructed display, with the skyline glowing behind you and reflections dancing across Lake Michigan. It’s a laid-back, front-row ...
Chicago
1+ Hours
Boat Tour
Chicago Blue Water Charters
Copy to Clipboard to Share
Chicago Playpen Anchorage Area
Anchor, unwind, and turn up the fun at Chicago’s Playpen hotspot!
Head out to the iconic Chicago Playpen, the city’s ultimate on-the-water hangout where boats gather, music plays, and the energy is unmatched. Drop anchor in this lively spot and soak up the sun with the North Side skyline as your backdrop—perfect for swimming, relaxing, and turning up the fun at ...
Chicago
1+ Hours
Boat Tour
Chicago Blue Water Charters
Copy to Clipboard to Share
22 FT Private Pontoon Cruise - 2 Hours
Starting at $350 | Cruise the Chicago river for 2 hours!
Enjoy cruising the beautiful Chicago River for 2 hours The 22 ft pontoon has more space and a table for snacks and drinks. BYOB and food or allow us to cater so you have less to carry. You are the driver. Our crew will give you or someone in your group a lesson when you arrive Gas Powered, automatic. ...
Chicago
2 Hours
Private Tours
Boat Tour, Pontoon Boat Rental
Chicago Boat Rentals
Copy to Clipboard to Share
Evening Boat Rentals (Fireworks )
Starting at $400 | 2 sizes available
Enjoy cruising the beautiful Chicago River for 2 hours. This cruise includes the famous firework show located next to Navy Pier. This offer is available only Wednesday and Saturday nights, Memorial Day through Labor Day. You are the driver! BYOB or we can cater Lifejackets provided (under 13 must be ...
Chicago
2 Hours
Boat Cruise, Boat Tour, Cruise / Large Boat, Evening Cruise, Fireworks Cruise, River Cruise, Sternwheeler/Riverboat
Chicago Boat Rentals
Copy to Clipboard to Share
Annual VIP Membership
$250 • 50% off pontoon rentals for the season, yacht discounts, VIP perks
When purchased, members receive: -50% off any size pontoon rental -$100 off yacht rentals -Access to member-only events -No fee for cancellations and reschedules After membership is purchased, an exclusive code will be emailed. The code is exclusive to the customer who purchased and can be used to receive ...
Chicago
Private Tours
Boat Tour, Cruise / Large Boat
Chicago Boat Rentals
Copy to Clipboard to Share
18 FT Private Pontoon Cruise - 2 Hours
Starting at $150 | Cruise the Chicago river for 2 hours!
Enjoy cruising the beautiful Chicago River for 2 hours You are the driver! Our dock crew will train you or someone in your group when you arrive. Gas Powered, automatic. simple to drive. BYOB and snacks are welcome or we will be happy to cater to you. Although our boats have bluetooth capabilities, we ...
Chicago
2 Hours
Private Tours
Boat Tour, Pontoon Boat Rental
Chicago Boat Rentals
Copy to Clipboard to Share
Private Boat Tour
For all ages! • 2.5 Hours
Join Dave for a cruise on the Chicago River in your own private vessel for up to 10 people. Learn about the Chicago skyline and how innovative architecture shaped the city and changed the world. Ditch the herd with the microphone and the same old speech for an interesting local perspective and find out ...
Chicago
2.5 Hours
Private Tours
Boat Tour
Chicago by Dave
Copy to Clipboard to Share
Historical and Architectural Lake & River Tour
April 2026-November 2026
🚤 Discover Chicago by Water: History, Architecture & Firefighting Legacy Step aboard and let our expert docents guide you through the fascinating story of Chicago—told from the best seat in the city: the deck of our historic fireboat. 🌆 World-Famous Architecture Marvel at Chicago’s skyline ...
Chicago
90m - 2hrs
Boat Tour
Chicago Fireboat Tours
Copy to Clipboard to Share
2026 Air Show Cruises
3.5 Hours | Unforgettable Event
This is going to be an unforgettable event! Rates Adult: $175 Child: $90 Duration 3.5 Hours About The Chicago Air & Water Show is an annual air show held on the shore of Lake Michigan in Chicago, Illinois. The show has been held each year since 1959 and is Chicago's second most popular festival. ...
Chicago
Boat Tour
Chicago Fireboat Tours
Copy to Clipboard to Share
51′ Sea Ray Sundancer Powerboat
All Ages • 3 to 8 Hours • Up to 12 People
An incredible boating experience! Duration Three to Eight Hours About The Yacht has a huge front of the boat that can fit the entire group plus a sun pad. The back seating area of the boat has a plenty of room and turns into a lounger. She is a two bathroom, two bedroom sailboat with a great dining and ...
Chicago
Boat Tour
Chicago Sailboat & Yacht Charters
Copy to Clipboard to Share
Day Cruise (Endless Summer)
For all ages! • 3-6 Hours • Up to 13 Guests
Welcome aboard the luxurious 32 ft Larson Cabrio, a spacious cabin cruiser designed for ultimate comfort and enjoyment. Relax in a cozy bedroom, prepare meals in the fully equipped kitchen, and freshen up in the convenient bathroom. Our amenities include two fridges to keep your refreshments cool and ...
Chicago
3-6 Hours
Boat Tour
Endless Summer Chi
Copy to Clipboard to Share
Architectural Tour
Most Popular • 3 Hours • All Ages • Online discount
Reserve online & Save $2 each! Paddle the architectural canyons of the Chicago River on our architectural tour! Join us as we embark on a voyage of history and architecture through downtown Chicago. Your tour begins with a lesson in paddle strokes, safety, and rules of the water. In addition, after ...
Chicago
3 Hours
Boat Tour, Kayak
Kayak Chicago
Copy to Clipboard to Share
City Lights Night Paddle
All Ages • 3 Hours • Online discount
Reserve online & Save $2 each! The city lights are gorgeous at night, and the Spring and Summer weather is perfect for an evening paddle. We will start at dark and paddle down the Chicago River to enjoy the city lights reflecting in the river and off the buildings. With lights on your boat we will ...
Chicago
3 Hours
Boat Tour, Kayak
Kayak Chicago
Copy to Clipboard to Share
Sunset on the Chicago River
All Ages • 3 Hours • Online discount
Reserve online & Save $2 each! Enjoy the sunset on the Chicago River. See the sunset as it reflects off of the towers of glass and steel and onto the water beneath you. Your evening begins with an orientation to kayaking. You will begin the evening by meeting your guides near the North Branch of ...
Chicago
3 Hours
Boat Tour, Kayak
Kayak Chicago
Copy to Clipboard to Share
St. Paddy’s Day Green River Tour
All Ages • 3 Hours • Online discount
Reserve online & Save $2 each! Come join us for St. Paddy’s day as we paddle the emerald water for the annual dying of the Chicago River! Be one of the few to experience the green water as thousands of on-lookers crowd the bridges and river banks. Paddle a single or double kayak or embark in our ...
Chicago
3 Hours
Boat Tour, Kayak
Kayak Chicago
Copy to Clipboard to Share
Lake Shore Skyline Paddle
All Ages & Skills • 2.5 hours • Save $2 each online!
Your skyline paddle tour begins with an orientation to paddling. You will learn basic paddle strokes, safety, and rules of the water. Once on the water, our guides will lead you along the shoreline for an incredible view of the city. Together we'll paddle past beaches & breakwalls truly experiencing ...
Chicago
2.5 Hours
Boat Tour, Kayak
Kayak Chicago
Copy to Clipboard to Share
Day Cruise
For all ages! • 3-6 Hours • Up to 13 Guests
Set sail with Poseidon Chicago Charters for an unforgettable daytime experience on the magnificent Lake Michigan! The Chicago skyline provides a stunning backdrop to your special occasion. Whether you're celebrating a momentous bachelor or bachelorette party, marking a milestone birthday, orchestrating ...
Chicago
3-6 Hours
Private Tours
Boat Tour
Poseidon Chicago Charters
Copy to Clipboard to Share
The Chicago River Cruise
For all ages! • 3-6 Hours • Up to 13 Guests
Embark on a captivating journey through the heart of the Windy City with a unique Chicago River cruise! Discover hidden gems and gain an entirely new perspective as you navigate the bustling waterways, where architectural marvels rise majestically along the banks. Imagine gliding past the lively Chicago ...
Chicago
3-6 Hours
Boat Tour
Poseidon Chicago Charters
Copy to Clipboard to Share
Contemporary Chicago Blues ~LIVE~ with Michael Charles!!
All ages • 2 Hours • Chase your Monday BLUES away!
Kick-off your week and join us for a 2-hour concert sail from 7pm-9pm every Monday this Summer. About We’ll help you chase your Monday BLUES away aboard the 148-foot Tall Ship Windy as you enjoy the breathtaking views of Chicago from the waters of Lake Michigan accompanied by the sweet sounds of the ...
Chicago
2 hours
Kid-Friendly
Boat Tour
Tall Ship Windy
Copy to Clipboard to Share
Independence Day Weekend Kick Off Sail
All ages • 2 Hours • Best View in the City Aboard 148 foot Schooner Windy
Duration 2 Hours About A SPECIAL EVENT SAIL! Treat yourself to an Independence Day Sail from the best seat in town! Order a cool drink from our bar, then relax and enjoy a leisurely evening listening to patriotic music and enjoying the Chicago skyline. The City of Chicago MAY also have fireworks on July ...
Chicago
2 hours
Boat Tour
Tall Ship Windy
Copy to Clipboard to Share
Fireworks Cruise!
A Chicago tradition aboard the Official Flagship of the City of Chicago
Duration 90 Min. The Wednesday Fireworks Boat Tour starts promptly at 8:45pm. The Saturday tour starts promptly at 9:15pm. About A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seat in town! Grab a cool drink from our bar, relax, and enjoy a leisurely ...
Chicago
Boat Cruise, Boat Tour, Cruise / Large Boat, Evening Cruise, Fireworks Cruise, Sailing
Tall Ship Windy
Copy to Clipboard to Share
Chicago Skyline Sail
All ages • 75 Minutes • Great for friends & family!
Duration Each sail is approximately 75 minutes. About AVAILABLE NOW SAIL DAILY MAY THROUGH SEPTEMBER! Leave the hustle and bustle behind! Explore Chicago’s shoreline, with a leisurely trip on Lake Michigan. Take in the world-famous skyline, enjoy spectacular views and discover the Windy City from the ...
Chicago
75 minutes
Boat Tour
Tall Ship Windy
Copy to Clipboard to Share
Viewing 1 to 25 of 28 Experiences