navy pier sailboat

Tall Ship Windy

Review Highlights

“ I was given an opportunity to help raise the sail , (hard work), and lots of great conversation with the crew. ” in 54 reviews

“ I was able to actually enjoy some downtime while the awesome crew regaled her with adorable pirate tales. ” in 65 reviews

“ (We took the water taxi to Navy Pier from near Union Station so water travel was kind of the theme of the day. ” in 65 reviews

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Location & Hours

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600 E Grand Ave

Chicago, IL 60611

Illinois St

Near North Side

Serving Chicago Area

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About the Business

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Scott and Hope S.

Business Owner

Explore Chicago’s scenic shores with a relaxing sail around Lake Michigan aboard Chicago's Official Ambassador Tall Ship Windy. Take in the world-famous skyline, enjoy spectacular views, and discover the Windy City from the water. Select from Skyline and Architecture Sailing Tours, Fireworks Sails, Educational Sails and Windy's Famous Friday Nite Pirates Pub Sail. Sailing from Navy Pier daily, Tall Ship Windy is a Chicago tradition and the last four-masted schooner built in the United States. At 148' feet, she is truly phenomenal to be on board. …

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Overall rating

472 reviews

A very enjoyable experience! Wife and I went out for a relaxing afternoon and got great views of Chicago. If we ever get back, we'll do it again! The crew members were a lot of fun and the prices at the bar were reasonable, being even to or slightly higher than what you'd expect to pay in the restaurants and bars around town.

Chicago skyline

Snore fest... Everyone on board was tired and told us so many times on the microphone. Lacked any type of pirate flare. No real sailing, the sails just flapped in the wind and 90 percent of the time no one held the helm and the wheel was spinning aimlessly back and forth with no one steering. $18 for a short run and coke. Some rude staff. We asked for the best place that they thought we should sit on the ship and the crew member answered "Just take a seat" and snarled. (Person with open shirt, scruffy blonde hair and unshowered look) The ship sat in front of the skyline for 45 m with people taking selfies everywhere. Incredible waste of money and time.

Went here on my birthday, it was amazing. The sounds of the water and the beautiful views. The boats aesthetic was so great and the crews outfits made it better. Alex had he best outfit though, he could really pass as a pirate. It made the experience so much more enjoyable. I recommend going here if you're planning to go on a boat.

Went on the Tall Ship Blues Cruise last night. The band was great! The sailing was not. We basically went 1/4-1/2 mile out from Navy Pier and sat. Not what I expected. Calling this a sailing cruise is not accurate

It was pretty fun. I'd definitely recommend it, even if you also do the river architecture tour, it's a fairly different experience. I'd say it's more about cruising and less about learning. The guy on the microphone eventually just started joking because while he had interesting facts, most people weren't really listening. The ship itself is impressive. It's laid out in a weird way but I enjoyed learning about it from the captain. There was a bar with snacks onboard and we all had a beer and watched the skyline go by. A great experience for locals or for people who are visiting. We went with my folks, in town from Texas.

Tall Ship Windy is a beautiful sail boat! Located at Navy Pier, it's a must have for anyone who loves sailing. I purchased the ticket online, and made reservation at the same time, online. It was pretty easy process. With the confirmation, I received the check-in instructions and directions to find the exact location. Check in was 15 minutes before sailing. On the boat, there was a bar with both alcoholic and nonalcoholic beverages, and some snacks for purchase. The crew members were entertaining and fun to watch the work done. They instructed everyone for safety and constantly kept us under control to keep us safe. The view of the city's skyline is amazing from the distance! I had a great time!

See all photos from Judit C. for Tall Ship Windy

Great time!!! Highly recommend! For kids and grown-ups. Tourists and Chicago natives as well.

The entire experience was fun. Great crew and guide. Interacted with us . Great experience to be on a schooner and watch and/or help hoist the sails. Passengers are free to walk around or sit. Tour guide was super. Highly recommend.

Great experience, entertaining crew. magnificent views of the skyline. Only negative: I wish there were no music so we could have enjoyed the quietness of the boat bobbing on the water.

did the fireworks cruise on Saturday, was great atmosphere, great spot for watching the fireworks. Matt from Tall Ship Windy stellar host, quite the character to keep you enticed and laughing. Mark from the Queen Blue not so good was visiting Chicago for first time so only thing would have liked is more fun facts stuff since it went quiet for some time but is possible is just wrong cruise for skyline info/stories.

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Choose Windy City Sailing for your Chicago Sailboat Charter

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LUXURY ACCOMODATIONS

Our sailing yachts accommodate 1 to 10 people. We offer charters with captain and crew for groups up to six (6) or a bareboat charter for groups up to ten (10) with a USCG Licensed Captain paid separately. With up-to-date amenities and two bathrooms onboard, we assure the comfort of all our guests.

CUSTOMIZED CHICAGO SAILING CRUISES

All private Chicago sailboat charters depart and return according to your schedule. All Chicago sailboat cruises have three-hour minimums. Charter extensions are available upon request. Yes, we encourage you to bring food and refreshments, including alcoholic beverages.

Our yachts are professionally maintained and equipped.  In addition, we certify, train and employ United States Coast Guard Captains with over 20 years of experience. Because of this, rest assured that you are in excellent hands.  Also, all of our captains are enrolled in USCG mandated drug screening programs.

CONVENIENCE

The yachts are at the North End of Belmont Harbor, just east of Wrigley Field—or 15 minutes from the Chicago Downtown area. Windy City Sailing is easily accessible via Uber, Lyft, taxis, and bicycles. Also, parking is available via the City of Chicago. Gift certificates are available for all Chicago sailboat cruises and bareboat charters. We confirm reservations with a 50% deposit, fully refundable with a seven-day notice. Gratuity is at your discretion (we recommend 20% to our outstanding crew).

SPECIAL EVENT YACHT CHARTERS

4th of July Sailing Charter

​ Each year, the Fourth of July Sailing Charter gives the citizens of Chicago the chance to witness some of the nation's most spectacular firework displays from the comfort of a boat. The tour has become increasingly popular and is one of the highest rated Independence Day activities.

Chicago Air Show Charter

​ Chicago Air and Water Show is a remarkable event that has long been captivating city dwellers. By taking a sailboat charter from us, you can experience the show from the lakefront. You won't need to fight the crowds for the best view, as you will be luxuriating on your yacht with an unparalleled outlook of the show.

Navy Pier Firework Charter

​ During summer, the Navy Pier gives us breathtaking firework shows. For an unforgettable experience, there is no better way to appreciate these amazing visuals than to charter a yacht . Our dedicated captains and crew members make sure that all your needs are taken care of, so you don’t have to worry about anything else. With our exclusive amenities, it is not even worth considering any other way to view these displays.

Book Your Chicago Sailing Trip Now

WITH WINDY CITY SAILING

We know you will have questions about sailing charters, so feel free to reach out via phone or email.

Please contact Edwina at 773.868.0096 or  [email protected]  for details and pricing.

Frequently Asked Questions

Have you ever wanted to sail but were unsure what it would cost to charter a private yacht? If so, Windy City Sailing is here to help with all your sailing–related questions. We have made things easy to find by categorizing our questions, and if there’s anything you can’t find, feel free to reach out. Our knowledgeable staff is here to answer all your questions about sailing along the wonderful Chicago Lakeside. From planning the perfect corporate outing for out-of-town guests to helping you witness the incredible  4th of July fireworks , we have it all covered!

Review our  FAQ

Preferred Partners

Preferred Partners are the resources we depend on to deliver the highest quality service to our guests. We value them and appreciate their services.

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Tour the Windy City from the water

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Architecture River Tour

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• 75-minute, guided boat tour
• Unique views from the water create an entirely new perspective of the city
• 40+ landmarks including the Tribune Tower, the Wrigley Building, and Marina City

Skyline Lake Cruise

• 45-minute cruise on Lake Michigan
• Stops on the North and South side of the lake front for two iconic skyline photo ops
• Spectacular views of Chicago’s iconic architecture

• Fireworks Tour
• Front-row views of the Navy Pier fireworks display
• View iconic landmarks
• Enjoy the illuminated Chicago skyline at night from Lake Michigan

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Sightseeing in Chicago? Chicago CityPass saves 48% on premier admission tickets  to Chicago’s top 5 attractions, including the Architecture River Tour.

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Now in its 83rd season, Shoreline Sightseeing operates Chicago's largest and most diverse fleet of cruise boats and water taxis with 11 major tour vessels and 7 water taxis.

(312) 222-9328 ext. 1 [email protected]

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5 reasons to experience the U.S. Sail Grand Prix Chicago at Navy Pier

Published on June 12, 2023 by Choose Chicago

The Rolex United States Sail Grand Prix Chicago at Navy Pier brings action-packed racing to Lake Michigan, Chicago’s Skyline Stadium , on June 16 – 17, 2023 to kick off the summer of racing.

National teams from the United States and all around the world will race hydro-foiling 50-foot race boats that literally fly over the water while sailing at 60+ mph speeds, thrilling crowds on land and on water, all in the heart of the Windy City. 

Chicago is the only freshwater venue in the world, and is the first event to open SailGP’s season four! Here are five reasons to come experience the adrenaline-fueled racing at Navy Pier:

1. Race boats that literally fly out of the water. Really! The F50 catamaran uses hydrofoils to lift out of the water and achieve highway speeds, faster than almost any power boat! This means close racing, crashes, capsizes, and drama — definitely not your normal day on the water.

2. Come for the party, stay for the racing! Tickets start at just $35 for general admission on Friday or Saturday. The Race Stadium opens at 3 p.m. and racing begins at 4 p.m. each day.

New to the festivities this year: the White Claw™ Beach Club. With panoramic views of the racecourse, the Beach Club is located right at the water’s edge and is the best place to witness the fast and furious racing action of SailGP. 

3. Feel the spray of the F50s flying by Navy Pier. SailGP brings fans closer into the action than any other sporting event with opportunities to meet world-class athletes on shore and catch a glimpse of the race boats up close!

4. Bring your own boat! Yes, Chicago’s Skyline Stadium really will feel like a race course and you have the opportunity to bring a boat (or ask a friend) and anchor right next to the race course for an unparalleled, up-close race experience!

5. Don’t have your own boat — no problem! Another new option is the On-Water Premium Presented By White Claw™ Spirits. Treat yourself to an exclusive race experience onboard the SailGP spectator boat fleet with unique viewing opportunities located immediately next to the race course.  

How to watch Sail Grand Prix

Join the party on land or on water! Navy Pier is race stadium headquarters and will host the weekend party to watch as the turbo-charged 50-foot race boats fly only a few feet away, across Chicago’s Skyline Stadium. Enjoy live music and DJs, premium food and beverage experiences, fan shops, big screen TVs, fireworks, and more!

Racing takes place between Navy Pier and Adler Planetarium, guaranteeing a front-row seat along the waterfront as well.

When is Sail Grand Prix

Race day 1 | Friday, June 16 SailGP Stadium | 3 p.m. – 7 p.m. Race times | 4 p.m. – 5:30 p.m.

Race day 2 | Saturday, June 17 SailGP Stadium | 3 p.m. – 7 p.m. Race times | 4 p.m. – 5:30 p.m.

Get more information and purchase tickets .

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Dock with us

The premier Lake Michigan boating destination

Located in the heart of iconic Navy Pier, Chicago’s only all-transient marina brings world-class amenities, service, dining, shopping, and entertainment directly to Lake Michigan’s boating community. Check back often for updates on our progress as we pioneer this one-of-a-kind facility in the heart of Chicago.

Something to look forward to

These amenities and more…coming 2025!

Docking options

We offer flexible, short-term docking options ideal for any type of guest: Loopers, locals, charters, sailing, yachting, boating clubs, and vacationers. Come for lunch, dinner, or some overnights. We look forward to seeing you on the docks!

5-Star Accommodations

With concierge assistance, seamless online booking, and 24-hour staffed surveillance, you’ll really be able to relax in Chicago.

Experience Navy Pier

Dock right in the heart of the world-renowned destination of Navy Pier! Step off the boat into hundreds of dining, shopping, and entertainment options in the heart of the city of Chicago.

Explore Lake Michigan

We serve boats up to 130’ with no minimum size requirements—however you enjoy Lake Michigan, Navy Pier Marina is happy to provide docking space. Take advantage of our on-site laundry, washrooms, showers, and bring your dog!

An unmatched boating experience

Welcome to Navy Pier Marina, the newest boating destination on Lake Michigan. We are excited to offer Lake Michigan boaters a one-of-a-kind Chicago experience–coming soon!

QUICK LINKS

2610 Lake Cook Rd, Ste 250 Riverwoods, IL 60015

(847) 444-5788

• [email protected]

Sign up for our newsletter to stay informed about Lake Michigan’s only dedicated transient marina construction progress, opening date, and how to reserve a slip.

Wilco front man Jeff Tweedy to headline annual ‘Chicago Live!’ performing arts festival at Navy Pier

C HICAGO — Wilco front man Jeff Tweedy will headline this year’s ‘Chicago Live!’ a free annual performing arts festival returning to the Navy Pier in September.

Chicago Live! exclusively features performances from Chicago-based and Chicago-grown artists across five stages at the Navy Pier over two days.

Organizers say this year’s event will be the largest yet and will feature performances from 111 different groups and artists.

Tweedy is set to kick off this year’s event with a solo acoustical set on the first evening of the festival.

“Chicago’s lakefront is one of my favorite places on earth and I’ll jump at any opportunity to play on its shores,” Tweedy said.

According to organizers, Tweedy’s performance at the festival will be his only solo concert to take place in the Chicago area this summer.

“Jeff Tweedy’s songs have been reaching fans across multiple genres for decades in ways that are both deeply personal and collectively shared,” Arnie Rivera, the Chief Administrative and Equity Officer for Navy Pier, said in a press release on Wednesday morning. “As a person and a performer, he embodies the spirit and inclusivity of Chicago Live! and we could not be more delighted to welcome him to this year’s festival.”

Chicago Live! Launched in 2021 as a way to reconnect audiences with the local performing arts community following a year-and-a-half of venue closures sparked by the COVID-19 pandemic. The annual event is supported by the Pritzker Foundation and Peoples Gas.

This year’s event will take place over two days, on Saturday, Sept. 21, and Sunday, Sept. 22.

Visit the Navy Pier website for more information or to view a full list of artists set to perform at the upcoming event.

For the latest news, weather, sports, and streaming video, head to WGN-TV.

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

Fireworks Cruise From Navy Pier Aboard Tall Ship Windy!

Quick details.

• Hour Glass Duration: 90 Minutes
• User Ages: All Ages
• Calendar Availability: Wednesdays & Saturdays from Memorial Day weekend through Labor Day weekend
• Sailboat Sail: Chicago Fireworks Cruise
• Map Marker Departure: Chicago's Navy Pier

The Wednesday Fireworks Sail departs promptly at 8:45pm. The Saturday Fireworks Sail departs promptly at 9:15pm.

See Stunning Fireworks over the Chicago Skyline

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. Sailing on Lake Michigan past the beaches and skyline, you will not only enjoy the stunning fireworks show, but also great music, stories and drinks. This is the famous fireworks sail on Lake Michigan, so book early as it sells out quickly.

• 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. On special sails like this one, trip insurance allows you to change or cancel your reservation and receive a refund up to 24 hours before your scheduled sail time. General Admission tickets on special sails without trip insurance may not change or cancel a reservation.

• Chevron down Add-on Trip Insurance

$8.00 Per Guest | Add to your ticket at checkout

On special sails like this one, trip insurance allows you to change or cancel your reservation and receive a refund up to 24 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 on special sails without trip insurance may not change or cancel a reservation.

• Chevron down Special Sails Cancellation Policy

All sales are final. General Admission tickets on special sails without trip insurance may not change or cancel a reservation.

• 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 24 hours before your scheduled sail time.

Related Sails

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Chicago Skyline Sail Aboard 148' Tall Ship Windy

Explore Chicago’s scenic shores and enjoy this Windy City boat tour with a relaxing sail around Lake Michigan. Take in the world-famous Chicago skyline, enjoy spectacular city views and discover the Windy City from the water. Select from Pirates and Maritime stories at 1pm, Architectural Tour and Skyline at 3pm and 5pm or a Chicago Sunset Cruise at 7pm.

• Frequently Sells Out

Chicago Skyline Sunset Sail

For the best Chicago sunset, visitors and residents alike, join us aboard the 148′ Tall Ship Windy – the official ambassador for the City of Chicago. Departing from Navy Pier daily, you will enjoy a spectacular sailing cruise and enjoy the breathtaking moments as the sun sets gently behind the Chicago Skyline. There is nothing like Chicago at sunset.

• WEATHER ALERT Flood Warning Full Story

Boating team sets new record in Chicago Yacht Club's Race to Mackinac

CHICAGO (WLS) -- While storms hurt some teams in the annual Race to Mackinac , it also helped one team set a new record.

The video in the player above is from a previous report.

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

Team Maverick made it all the way to Mackinac Island in 22 hours, 24 minutes, and 23 seconds, beating the previous record set 22 years ago by more than an hour.

Three boats in the Race to Mackinac were damaged from Saturday night's storms.

The Chicago Yacht Club said the boats reported dismasting and thankfully no one was injured.

Video was shared with ABC7 by Parade of Boats before storms moved in.

The Race to Mackinac is the world's longest annual freshwater race. The length of the race is 333 miles from Navy Pier to the Round Island Channel, just off of Mackinac Island, Michigan.

More than 250 boats and 2,100 racers from around the world participated in the race. The first Race to Mackinac took place in 1898.

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Race to Mackinac gets underway Friday

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City Politics | Navy announces $78 million workcenter for…

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Subscriber only, city politics | navy announces $78 million workcenter for sailors, shipyard workers in newport news.

Naval Sea Systems Command (NAVSEA) wrote in LinkedIn post that the funding is for the planning, design, and construction of a carrier refueling overhaul workcenter for sailors’ and shipbuilders’ use while assigned to ships in refueling and complex overhaul at Newport News Shipbuilding.

“The building will provide approximately 80,000 square feet of dedicated space near the ship that will include office spaces for sailors and shipbuilders, as well as a fitness center, counseling offices, and other areas sailors can utilize while executing RCOH,” the post read.

Plans are for construction to be complete by June 2026. NAVSEA said it is “committed to quality-of-service improvements for our sailors and shipbuilders at Newport News Shipbuilding.”

HII spokesperson Todd Corillo said the building will be located mid-yard, between the dry dock and the outfitting pier that support refueling and complex overhaul work. He said the process for selecting a contractor is underway.

Naval Sea Systems Command did not provide any comments by press time.

The work center is one of many recent announcements the Navy has made regarding improving the quality of life for shipyard workers and sailors assigned to ships in maintenance periods. Many of these efforts were made in response to a wave of suicides among Hampton Roads-based sailors.

Last year, the Navy announced a series of upgrades , including off-ship housing, free Wi-Fi and more access to food for USS John C. Stennis sailors while the aircraft carrier undergoes a multiyear refueling and complex overhaul at Newport News Shipbuilding.

Additional plans are also in the works. A vice admiral announced this month that the Navy is looking at creating 8,000 new beds for sailors in Hampton Roads and that 1,000-1,500 beds would likely be in Newport News.

Last month, the Navy and Newport News Shipbuilding announced the construction of a new parking garage that will bring 2,000 new parking spaces to downtown Newport News for use by shipbuilders and sailors assigned to the shipyard.

Josh Janney, [email protected]

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Now Open The Butterfly House at Navy Pier

Walk through this immersive exhibit in a safe, family friendly environment with hundreds of live butterflies from all over the world.

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Jul. 18, 2024

Navy Pier After Dark

Navy pier’s nightlife scene after dark, is unmatched, with fireworks, cocktails, and live music all in one place., nightlife on navy pier is unlike anywhere else in the city of chicago after dark. from firework displays to cocktails and live music, navy pier has it all., navy pier fireworks after dark.

Navy Pier has been named ‘ Best Place to See Fireworks ‘ for the second year in a row in the USA TODAY 10Best Readers’ Choice Travel Awards contest. Whether you choose a cozy spot on the Pier or a prime viewing location, the spectacle promises to be a highlight of your evening in Chicago.

So, experience the magic of summer nights at Navy Pier. The Pier offers breathtaking fireworks illuminating the sky every Wednesday and Saturday night!

Moonlit Adventures with Night Cruises on the Pier

Next, embark on an unforgettable adventure at Navy Pier with numerous options for Chicago boat tours and cruises at night.

Whether you crave the thrill of a Shoreline Lakefront Fireworks Cruise  or the elegance of City Cruises , we cater to every desire. For those enchanted by history and immaculate skyline views, set sail on the Tall Ship Windy Sunset and Skyline Sail , where tales of the city unfold against a spectacular back drop.

At Navy Pier, the night is yours to explore, with each cruise promising an experience as unique as the city itself.

Sunset Cocktails

As the sunsets, the night comes alive with the promise of a refreshing beverage. From the roof heights of Offshore Rooftop to the relaxed atmosphere of the Beer Garden , and the island-inspired cocktails of Jimmy Buffett’s Margaritaville Bar and Grill , each venue offers a unique experience. Don’t forget to swing by Windy City Ribs for your favorite menu items, craft cocktails, and whiskey bar, ensuring you savor the same great food, service, and vibes all night long.

Whether you’re savoring skyline views, enjoying a laid-back beer garden vibe, or indulging in tropical drinks, Navy Pier’s restaurants and bars promise the perfect setting for an unforgettable evening. Because no visit to Navy Pier is complete without discovering its diverse dining and bar scene, where every sip is a taste of Chicago’s vibrant spirit.

Rhythms by the Water: Live Music Series

Navy Pier offers a variety of live music options with events nearly every day. From Skyline Sessions to Wave Wall Wax, there’s something for everyone.

Wave Wall Wax features top Chicago DJs on Saturday playing your favorite house and dance music. While Skyline Sessions , showcases solo artists and small ensembles against the stunning skyline on Thursdays and Fridays. Additionally, Live on the Lake! presents Chicago’s best bands and national acts every weekend.

Get together with friends, enjoy the music, and relax with the lovely lakeside and city views.

Centennial Wheel After Sunset

Finally, take a ride on the iconic Navy Pier Centennial Wheel. This Chicago Ferris Wheel operates until 10 PM on Fridays and Saturdays, and until 9 PM Sunday through Thursday during the summer season. Rising nearly 200 feet above ground, it offers sweeping 360-degree views of the Chicago skyline and Lake Michigan. Its enclosed gondolas ensure a comfortable experience and breathtaking scene, no matter the time of the year.

The Centennial Wheel also offers a special VIP experience after dark. Featuring a glass-bottomed gondola, plush seating, and other exclusive premium amenities for guests. Whether celebrating a special occasion or attempting to create lasting memories, guests can reserve the VIP Gondola in advance through online booking.

In essence, with so much to explore at Navy Pier after the sun goes down, be sure to check our calendar for the latest events and public programming before planning your visit.

More Information

Summer fireworks are best at Navy Pier.

Take a cruise on Lake Michigan now!

Grab your favorite cocktail at one of our spots.

Experience the best of live music after dark!

Best views of Chicago on the Centennial Wheel.

Watch the sunset over the water with a beverage!