chicago lake michigan sunset cruise

Chicago Sunset Cruise

Resumes April 19, 2024

Awe-inspiring with a casual vibe, watch the sun slowly set behind Chicago’s architectural backdrop. This lake cruise is light on narration and heavy on incredible and spectacular!

Schedule & Tickets

• Adult: $44.00
• Child (4-12): $20.00
• Under 4: Free (ticket required)

TICKETS ARE NON REFUNDABLE BUT ARE TRANSFERABLE.

• Parking & Directions
• More Information
• Boarding begins 15-30 minutes prior to scheduled departure time.
• All bags are subject to inspection.
• Prohibited Items: Outside Alcohol, Weapons of any kind (Firearms, Knives, etc.), Flammables, Explosives.

Your boat includes:

Drinks & Snacks

Full-service bar with wine, local beer, and craft cocktails, as well as an assortment of snacks, all for purchase. Pinkies up!

Climate-Controlled Lounge

Keeping you cool when it's warm and warm when it's cool (or freezing).

No need to hold it. We have changing tables for the little ones who don’t know what holding it is.

BOOK YOUR EXPERIENCE NOW

Vote Tall Ship Windy for USA Today's 10 Best - Best Boat Tour. Click to vote!

• Frequently Sells Out

Chicago Skyline Sunset Sail

Quick Details

• Hour Glass Duration: 75 Minutes
• User Ages: All Ages
• Calendar Availability: Daily
• Sailboat Sail: Chicago at Sunset Cruise
• Map Marker Departure: Chicago's Navy Pier

The famous Tall Ship Windy Sunset Sail is truly famous. Used in many world-renown photos, backdrops for special events, weddings and evenings out, the sunset sail aboard one of the only four-mast Schooners still in operation will not disappoint. You will enjoy a sail on Lake Michigan and at just the right moment, S/V Windy will gently turn toward the Chicago skyline for a view of our spectacular sunset. Sit back and relax, enjoy some soothing music and gently complete your day with this dramatic sunset.

Chicago’s Tall Ship Windy Sunset Cruise departs Navy Pier promptly at 7pm. The sunset cruise tends to sell out so we highly recommend the purchase of VIP tickets to ensure your choice of seating.

• Chevron down Beginning September 3: Enjoy a Sunset Skyline Sail at 5pm and a Late Summer Twilight Sail at 7pm

Our sailing schedule changes with the season. Beginning September 3, enjoy a Sunset Skyline sail at 5pm and a Late Summer Twilight Sail at 7pm.

On our Twilight Sail, enjoy the beautiful colors splashed across the post-sunset sky. You’ll enjoy an evening sail on Lake Michigan aboard Tall Ship Windy and take in the world-famous Chicago skyline as day transitions to night.

• Chevron down Board First with VIP Captains Boarding - Limited Tickets Available!

All seating on board Tall Ship Windy is first come, first served. Guests with  VIP Captains Boarding  tickets board first before General Admission ticket holders. A limited number of VIP tickets are available and are likely to sell out. Board first to choose your seat on one of Windy’s three decks: the forward, middle or aft.

All VIP Captains Boarding tickets also include trip insurance. Trip insurance allows you to change or cancel your reservation and receive a refund up to 8 hours before your scheduled sail time. General Admission tickets without trip insurance may only change or cancel a reservation and receive a refund up to 48 hours before their scheduled sail time.

• Chevron down Add-on Trip Insurance

$8.00 Per Guest | Add to your ticket at checkout

Trip insurance allows you to change or cancel your reservation and receive a refund up to 8 hours before your scheduled sail time. Refunds for cancelled charters are less the $8.00 cost of insurance and 3% booking fees.

General Admission tickets without trip insurance may only change or cancel a reservation and receive a refund up to 48 hours before their scheduled sail time.

• Chevron down Cancellation Policy
• RAIN OR SHINE EVENT: In the unlikely event that your tour is cancelled, you may exchange your ticket for another day or receive a refund.
• No-shows will not be eligible for rescheduling or refund. Guests must arrive at least 30 minutes before the scheduled departure time or risk forfeiture.
• The Captain reserves the right to postpone a sail for up to 15 minutes in the case of passing inclement weather.
• Add-on Trip Insurance: Allows you to change or cancel your reservation and receive a refund up to 8 hours before your scheduled sail time.

Related Sails

• Hour Glass 90 Minutes

Fireworks Cruise From Navy Pier Aboard Tall Ship Windy!

Watching fireworks from Navy Pier has become a Chicago tradition and there is no better seat in the house to watch the show than sailing aboard 148′ Tall Ship Windy – the Official Flagship of the City of Chicago! Order a cold drink from our bar and enjoy a thrilling fireworks performance as you sail along the stunning and iconic Chicago skyline during this special event sail.

• Great for Children!

Educational Sail: Tall Ship Discovery Sail

History comes alive on this exciting Windy City boat tour. Enjoy an educational adventure for curious minds of all ages with the backdrop of the iconic Chicago skyline always in view. Led by our crew-educators, experience a hands-on sailing excursion in Chicago aboard Windy.

• Searay sundacer 35′ powerboat
• fireworks-sunset-cruise-wed-sat-nights
• Wheather Links

Testimonials

• Map of Chicago

(312) 587-3474

Chicago sunset cruise, sunset cruise.

Relax and Enjoy the Sunset!

Lean back and relax as you glide over the lake on a Four-hour sunset cruise. Bask in the glow of the setting sun and take in the breathtaking view of Chicago’s skyline.

As you set sail, the cruise will take you onto Lake Michigan, passing by beautiful landmarks such as the famous Willis (formerly Sears) Tower and the John Hancock Building.

Chicago's Breathtaking Boat Trip and Sunset Cruise

Want to spend a low-key evening away from the hustle-bustle of the city?

Prepare to be mesmerized by the stunning beauty of the sun gracefully setting behind Chicago’s magnificent skyline on a relaxing cruise trip. This premier voyage offers a relaxed yet vibrant atmosphere, allowing you to appreciate the breathtaking scenery while enjoying refreshing drinks.

Our Boat Rides Provide Chicago's Best Sunset Experience

Chicago is a stunning spectacle to behold during sunset. The famous skyline contrasts the fading colors of the setting sun, and our sunset boat ride in Chicago offers unmatched city views from afar. We’ll bet there isn’t a prettier spot in the city to capture the dipping sun.

1300 S Linn White Dr, Chicago, IL 60605

Contact/directions, chicago sailboat and yacht charters ©2023 all rights reserved.

Thank you for visiting our site! We noticed you are using a browser we no longer support. To have the best overall experience and avoid issues navigating the site, please click one of the supported browsers to the right to download the latest version for free:

Search Site

Back to Menu

Unforgettable views. Unparalleled experiences.

Cruises & Tours

Explore chicago by land, water or air.

Whether you’re in town for just one day or are a life-long resident, cruises and tours of Chicago are a great way to see the sights, discover something new, or treat yourself to an unforgettable experience.

From laid-back sightseeing cruises and elegant dining cruises to heart-pumping thrill rides to upscale private charters, Lake Michigan and Chicago River cruises departing from Navy Pier offer a memorable experience for all.

Our Cruises & Tours

Architecture & Sightseeing Cruises

Take in Chicago’s iconic skyline and the scenic Chicago River with sightseeing cruises at Navy Pier! These fun experiences offer guests panoramic city views along with entertaining and enlightening commentary about Chicago’s architecture and history.

Brunch, Lunch and Dinner Cruises

When you dine on Like Michigan, every table is the best in the house. Navy Pier’s brunch, lunch and dinner cruises pair world-class cuisine with panoramic views of the city and lakefront.

Speedboat Tours and Thrill Rides

This isn’t your parents’ leisure cruise! On these 30-minute speed boat rides, you’ll tear across Lake Michigan at up to 45 miles per hour while getting entertaining and informative commentary on Chicago.

Specialty and Holiday Cruises

There’s always something worth celebrating with cruises on Lake Michigan and the Chicago River. Our partners offer themed cruises for major holidays, as well as a wide variety of special events that are sure to get you in the party mood.

Groups And Private Charters

Perfect for corporate outings and special occasions, group cruises and private charters offer unforgettable experiences for up to 800 guests.

Bicycle Tours

Bike & Roll Chicago allows guests to rent bicycles for a fun experience on the lakefront.

Cruise & Tour Types

Shoreline Architecture River Tours

Take Shoreline’s award-winning 75-minute Architecture River Tour to discover Chicago’s renowned landmarks as presented by our expert and entertaining guides. You’ll learn how Chicago rose...

City Cruises – Premier Dinner Cruise on Lake Michigan

Lake Michigan dinner cruises are the perfect setting for celebrating with friends, connecting with colleagues, or a romantic evening. Odyssey Lake Michigan dinner cruises are...

City Cruises – Premier Lunch Cruise on Lake Michigan

A two-hour Lake Michigan lunch cruise is the perfect way to enjoy time with family or the company of great friends. Retreat from a busy...

City Cruises – Signature Dinner Cruise on Lake Michigan

Celebrate a special occasion, host a group event or share a romantic evening aboard Spirit of Chicago. Great for parties of all sizes, a Spirit...

City Cruises – Spirit of Chicago Dinner Cruise

Catch the Chicago skyline at sunset during the most beautiful time of the year, and join us for a fun, laid-back, 2-hour cruise. Spirit's Lakefront...

City Cruises – Odyssey Lake Michigan Dinner Cruises

Odyssey Lake Michigan presents special prix fixe dinner cruises, offering guests the opportunity to try one of Chicago’s most unique dining experiences at an incredible...

City Cruises – Spirit of Chicago Brunch Cruises

Whether you’re a native Chicagoan, newcomer, or just visiting, a Spirit of Chicago brunch cruise is the perfect weekend outing. See well-known Chicago attractions from...

City Cruises – Signature Lunch Cruise on Lake Michigan

With the sunshine reflecting off the lakefront, there’s no better place to enjoy an afternoon in Chicago than aboard a lunch cruise. Departing from Navy...

City Cruises – Seadog River and Lake Architecture Tour

Enjoy Chicago’s iconic skyline with an exciting architecture cruise on the Chicago River. Departing from Navy Pier, this 75-minute narrated cruise is the best way...

City Cruises – Seadog Lakefront Speedboat Tour

Our Lakefront Speedboat Tour is the best way to view Chicago from the lake, combining an exciting speedboat ride along the shoreline with informative and...

City Cruises – Seadog Extreme Thrill Rides

With exhilarating high speeds and full 360° spins, this jet-propelled ride blasts off to start and splashes down to stop. Experience full throttle slalom runs,...

City Cruises – Odyssey Lake Michigan Brunch Cruise

This two-hour brunch cruise on Odyssey Lake Michigan, departing from Navy Pier, is ideal for capping off an incredible weekend. Enjoy a delicious menu stocked...

City Cruises – Odyssey Lake Michigan Groups

Host a truly unforgettable event on Lake Michigan. Book your group aboard one of Odyssey's regularly scheduled lunch or dinner cruises, or have an event...

Shoreline Sightseeing Group Tours

Adventures are meant to be shared. Turn your next family gathering or corporate outing into an awesome adventure by booking with Shoreline. We offer special...

City Cruises – Chicago Elite Private Events

It's your yacht. Let our professional event planners create a custom event just for your group aboard the Chicago Elite. With two fully enClosed ,...

City Cruises – Seadog Groups

Planning a special outing for your group? Charter Seadog for an event everyone will enjoy! With the ability to travel both the lake and river,...

Shoreline Sightseeing Water Taxis

Shoreline Sightseeing’s water taxis are a great way to get around town. Starting in May and running through September, our water taxi service offers fast...

City Cruises – Spirit of Chicago Group Cruises

Host an event unlike any other in the city! Book your group aboard one of Spirit’s regularly scheduled lunch, brunch, cocktail or dinner cruises, or...

City Cruises – Premier Brunch Cruise on Lake Michigan

Experience the city’s most unique floating event venue! City Cruises offers all-inclusive packages, chef-prepared menus, full bar options, and entertainment customized to fit your needs—all...

City Cruises – Signature Brunch Cruise on Lake Michigan

Shoreline Skyline Lake Tours

Shoreline’s 40-minute Skyline Lake Tour offers a relaxing way to experience the panoramic of the city’s famed skyline as seen from majestic Lake Michigan. The...

Tall Ship Windy Chicago Skyline Sail

Tall Ship Windy is closed for the season and will reopen in May 2024. Visit the Tall Ship Windy website to stay up to date...

Tall Ship Windy Private Charters & Weddings in Chicago

A Beautiful Stage for Your Event Set sail on Windy for weddings, parties, corporate functions, reunions, church outings, tour groups, team building and more! Windy...

Festivals, Fairs & Special Events

Chicago women’s pride fireworks cruise.

• Share this post:

3-Hour Evening Cruise on Lake Michigan. Enjoy the Lovely Night Sky, Dancing, Cocktails and the Amazing View of the Chicago Skyline aboard the Cozy, Classy and Luxurious Free Spirit Yacht as we Catch the Sunset and await the Fireworks Show. Offering Open Bar and Complimentary Appetizers with LIVE music by Chicago’s Own DJ GLORIA.

Return to events calendar

Explore hotels, flights, deals, and more

Plan your trip.

Chicago Newsletter

Stay in the know.

Visitors Guide

Start planning today.

Get the guide

Your Favorites

Quick access links.

Chicagoans find confidence and adventure sailing on Lake Michigan

3rd coast cruising, a sailing academy, has helped hundreds of chicagoans — many over the age of 50 — discover new adventures on the lake..

3rd Coast Cruising participants set sail on Lake Michigan.

3rd Coast Cruising

From the helm of his 38-foot catamaran on Lake Michigan, sails hoisted and billowing in the wind, Capt. Jim Miranda has spotted magnificent double rainbows, “roll clouds” that resemble Death Star lasers cutting across the sky and sunsets that leave him and fellow sailors speechless.

“There is no end to the tapestry that Mother Nature can paint over the city,” said Miranda. As owner of the sailing academy 3rd Coast Cruising, he has taught hundreds of Chicagoans, including many over the age of 50, to tackle the lake’s fickle and challenging conditions.

“A lot of our students are in [a phase of] metamorphic change,” Miranda said. “They’ve recently gone through a divorce or heartbreak, or death, or they moved to Chicago and didn’t know anybody. And they’re looking to figure out who they are again. … Sailing is that vehicle, and they develop confidence they never knew they had.”

Batavia resident Scott Marquardt, 63, discovered sailing as a way to reconnect with his reputation as a “water guy.” It started in the Navy and extended to annual family canoe trips in the Wisconsin River until 2017, when the water level rose and Marquardt was forced to seek an alternative. Google and Yelp led him to 3rd Coast, and he was hooked by the challenges it presented.

“In sailing, no matter how much experience you have, every year, you’re stunned at how much more you have to learn,” said Marquardt, who trained under Miranda to reach the rank of “skipper” and take out boats on his own.

Marquardt’s most memorable sailing trips are ones where something goes wrong — never to a life-threatening degree, but sometimes the wind dies, or the water chops a little harder than normal. Perhaps he got wet. Challenges have always led to discoveries, he said, like the time the wind was blowing hard to the east and he joked to Miranda that they should try sailing in reverse. They did, and it worked.

Susan Maivald, a 58-year-old Skokie native, sailed for the first time on her 52nd birthday, and the experience set her life on a new tack. She and husband, Jim, a lifelong sailor, eventually owned two boats — they named them the “Lucille Marie” and “Clara Marie,” for their respective mothers — and would race against fellow Waukegan Yacht Club members on Wednesdays. They took longer trips across the lake to Michigan, spending last summer harboring in cities along the coast meeting other sailors, floating under the stars and playing poker for Splenda packets. Jim died late last year. Susan and her friends are planning to sail as a group and spread her husband’s ashes in Lake Michigan.

One of the most important lessons sailing taught Maivald was how to let go.

“[Jim] would say, ‘You need to know your boat,’” she said. “I trusted him, and I’m still here.”

To get started sailing, Marquardt recommends purchasing a trial membership or introductory lesson with a local sailing club, like 3rd Coast or Columbia Sailing School (prices range from $50 to $300), and joining Facebook groups like “Chicago Sailors.” The sailing community is a close-knit but welcoming, Miranda said. He points beginners to Monroe Harbor, which is known as the “Sailors Circle” because the nearby Loop buildings absorb some of the wind, creating calmer conditions.

He also said that the right mindset can make all the difference. Prepare for rough seas and embrace the adventure, Marquardt advised.

“If you’re worried about getting wet or cold, or how the boat might seem tipsy, make a deliberate decision not to have those worries,” he said. “There’s a ‘seize the day’ aspect to it.”

• Chicago-area stages are primed for a summer filled with comedy, drama, musicals, magic and more

Mercury Cruises kicks off boating season this week on Chicago River, Lake Michigan

M ercury Cruises is about to kick off its 89th season on the Chicago River and Lake Michigan, and this year it is offering a whole new kind of tour.

The Mercury Cruises season starts this Friday.

ABC7 Chicago is now streaming 24/7. Click here to watch

Captain Alejandro Rodriguez joined ABC7 on Wednesday to talk about the boating experience.

New this year is the "Creepy Cruise." It starts after dark.

Rodriguez about the offerings and what makes Mercury unique. He also spoke about his experience as a captain.

The full interview can be viewed in the video player above.

For more information, visit the Mercury Cruises website .