navy pier yacht cruise

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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 Breeze Dinner Cruise is the perfect way to kick back, relax and take in the best of the city.

Select Dates from May – September

• A two-hour dinner cruise on Lake Michigan
• A tasty  Lakefront Breeze dinner menu
• Private table with the best views of Chicago’s skyline
• DJ and dance floor, interactive games (shuffleboard, giant jenga, etc.)

+1 (312) 222 2508

600 E Grand Ave, Chicago, IL 60611

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Your guide to Navy Pier

Completed in 1916, Navy Pier is undeniably one of Chicago’s top attractions. Stretching into Lake Michigan, this year-round destination truly comes to life in the summer, with fireworks displays, live music, theatre, and cruises setting sail daily. Come fall and winter, Navy Pier is still hopping, with special events, sights, and activities that span all ages and interests. Here’s just a glimpse of the fun to be had at Navy Pier.

Rides and games at Navy Pier

Centennial Wheel : The Centennial Wheel soars to nearly 200 feet, with year-round, climate-controlled gondolas for the most spectacular Ferris wheel ride ever. It’s an iconic part of the Chicago skyline and a treasured piece of Chicago history, harkening to the city’s 1893 World’s Fair. You can even book a VIP Centennial Wheel experience in a glass-bottomed, plush-seated gondola.

Pier Park : Pier Park is the epitome of fun. It’s where you’ll find the amazing Centennial Wheel, the Pepsi Wave Swinger, a 1920s-inspired musical carousel, and other nostalgic fairground rides — all with breathtaking skyline and waterfront views.

Amazing Chicago’s Funhouse Maze : This is Chicago’s only self-paced, full sensory maze experience. Navigate your way through 4,000 square feet of tunnels, mazes, and games.

Amazing Chicago’s Time Freak Game : Race against the block to gather points during this high-speed, all-ages game.

Cultural attractions and museums

Chicago Children’s Museum : Kids dig for bones on a dinosaur expedition, scale a three-story schooner, and even make a splash in a water playground. Chicago Children’s Museum is three floors of unadulterated fun for kids aged 10 and under. Don’t miss the Chicago Children’s Museum store while you’re there for fun, educational, and imagination-expanding toys and games.

Chicago Shakespeare Theater : This Tony Award-winning theatre hosts more than 650 performances a year, with a year-round season that presents plays, musicals, world premieres, and visiting touring companies. The theatre is particularly celebrated for The Yard, an engineering marvel in stage design, consisting of nine moveable towers that can be reconfigured to accomplish the vision of each production.

Outdoor adventures at Navy Pier

Boat cruises and tours : Whatever’s on your cruise wish list, you’ll find it at Navy Pier. Cruise on Lake Michigan and the Chicago River and experience everything from laid-back sightseeing and elegant dining to heart-pumping thrill rides and private charters. There’s even a cruise you and your dog can enjoy.

Bus and bike tours : Access any number of Chicago tours from Navy Pier, including Chicago Big Bus Tours, architecture and sightseeing cruises, Navy Pier food and history tours, and Bike & Roll Chicago tours. You can also rent bicycles to explore the lakefront at your own pace.

Public art and exhibitions : Navy Pier presents a rotating array of contemporary art designed to excite and inspire visitors. An ever-evolving schedule of art installations and exhibits keeps Navy Pier’s art scene hopping throughout the year.

Polk Bros Park : Polk Bros Fountain and Plaza at the entry to Navy Pier features a dramatic fountain with more than 150 jets that mimic the movement of waves, schools of fish, or flocks of birds. The Performance Lawns include two performance spaces to host live arts and cultural events, with Lake Michigan and the Chicago skyline as their backdrops. Definitely stop in at The Peoples Energy Welcome Pavilion, too, for information about things to do and see at the pier, guest maps, and more.

Navy Pier restaurants and bars

Beer Garden : This seasonal beer garden is one of Chicago’s go-to destinations for free, live, outdoor music. This lakeside venue also offers some of the city’s best lake and skyline views.

Offshore Rooftop & Bar : The nation’s largest rooftop bar, Offshore Rooftop & Bar offers panoramic lakefront and city views from atop Navy Pier’s Festival Hall. The space features a full-service kitchen, creative cocktails, cozy fire pits, and lounge seating.

Chef Art Smith’s Reunion : It’s all about coming together over simple, delicious food at Reunion, a welcoming and family-oriented spot helmed by acclaimed chef Art Smith. The menu offers comforting dishes with Southern flavors.

There’s a never-ending array of food options on the Pier , representing some of Chicago’s most well-known cuisine. Here are just a few options:

• America’s Dog & Burger : Classic Chicago-style dogs and more
• Beat Kitchen Cantina : An outpost of a beloved neighborhood venue
• Big Bowl Chinese Express : Fast and casual Asian cuisine
• Billy Goat Tavern : Home of the world famous “cheezborger”
• Garrett Popcorn Shops : A local legend, don’t miss the classic Garrett’s Mix
• Giordano’s : Iconic deep dish pizza, an only-in-Chicago experience
• Harry Caray’s Tavern : Barbecue, local craft beer, and sports memorabilia
• Lirica : Elevated Latin-inspired fare with sweeping waterfront views
• The Original Rainbow Cone : A Chicago classic, five flavors piled high on a cake cone

Navy Pier summer fireworks and events

The annual summer fireworks at Navy Pier are a favorite among locals and visitors alike, drawing crowds to the lakefront for the twice-weekly show.

The summer fireworks display traditionally takes place on Wednesdays and Saturdays between Memorial Day and Labor Day. The show typically starts between 9:30 and 10:15 p.m., check the latest schedule for details.

You can see the fireworks from most areas of the lakefront immediately north and south of Navy Pier. But the show is particularly stunning from atop the Centennial Wheel or on an evening lakefront fireworks cruise.

Summer also brings a full line-up of fun and free events to the Pier. Check out some of the music, fitness, food, and family-friendly events you can expect each summer:

• Neighborhood Artisan Markets and Workshops
• Wave Wall Moves dance series and Wave Wall Wax DJ sets
• Live on the Lake! concerts at the Miller Lite Beer Garden
• Pier Fitness classes and Sunset Yoga
• Water Colors live jazz series
• Water Flicks outdoor movie screenings

Check out the Navy Pier events calendar for more.

Sable at Navy Pier

Sable at Navy Pier , part of the Curio Collection by Hilton, is the first and only hotel right on Navy Pier. Each room features jaw-dropping vistas of the surrounding lake and city skylines. Along with can’t-be-beat views, the hotel also features Lirica , with Latin-inspired cuisine, an expansive bar, and spacious outdoor seating with waterfront vistas. The best part of the Sable hotel — it’s just steps away from everything Navy Pier has to offer.

Accessibility at Navy Pier

Navy Pier is continuously working to create an inclusive environment where everyone feels welcome. Accessibility accommodations include wheelchair rentals, accessible parking and attractions, resources for those who are deaf or blind, and beyond. Learn more about accessibility at Navy Pier .

Getting to Navy Pier

Navy Pier RTA The Regional Transportation Authority (RTA) trip planner makes it easy to use CTA, Metra, and Pace buses and trains with real-time next-bus and next-train travel information. Access the latest transit information and the RTA trip planner .

Navy Pier Metra Transfer from your Metra train to CTA buses and travel directly to Navy Pier. Use CTA bus #124 from Union Station, Ogilvie Station, and Millennium Station and CTA bus #29 from LaSalle Street Station and Millennium Station. Plan your route .

Navy Pier CTA bus The following bus routes all serve Navy Pier: #29 State (serving Metra lines from LaSalle Street Station and Millennium Station) #65 Grand #66 Chicago #124 Navy Pier (serving Metra lines from Union Station, Ogilvie Station, Millennium Station) #2 Hyde Park Express (during weekday morning and evening rush hours only)

Taxis and rideshare You can get to Navy Pier via taxi and rideshare from anywhere in the city. In addition to hailing taxis, you can e-Hail and e-Pay with CHICABS -approved apps ARRO and CURB . Credit cards are accepted in all taxis.

Parking Navy Pier has two on-site parking garages , West Garage and East Garage. Self-park rates start at $16 for one hour. Discounted parking is available at select off-site parking garages.

Valet parking is available at Entrance 2, located just past the entrance and exit to West Parking. The Pier offers complimentary electric vehicle charging stations in both the East and West garages.

From this article

Theater & Performing Arts

Chicago shakespeare theater.

Streeterville

Tours & Attractions

Food & Beverage

Offshore rooftop.

Sports & Recreation

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Chef Art Smith’s Reunion

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• United States
• Chicago / Illinois
• River North (Chicago)

Odyssey Cruises Lake Michigan

• Great for scenic views
• Good for special occasions

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Additional information

• Dining style Casual Elegant
• Price $50 and over
• Cuisines Dinner Cruise, American
• Hours of operation Brunch: Sunday: 11:15am - 2:00pm Lunch: Monday - Friday: 11:00am - 1:45pm, Saturday: 12:30pm - 3:30pm Dinner: Monday - Thursday: 6:00pm - 10:00pm, Friday - Saturday: 7:00pm - 11:30pm, Sunday: 5:30pm - 9:00pm
• Phone number (888) 957-0181
• Website http://www.odysseycruises.com/chicago
• Payment options AMEX, Discover, Mastercard, Visa
• Dress code Smart Casual
• Private party facilities Nothing compares to the dynamic, unique experience of a group event on the water. Delicious food and drinks, top entertainment and stunning views combine for an experience your guests won’t forget. Aboard our ships events from business meetings to special celebrations take on a whole new energy.
• Private party contact Professional Event Planner: (866) 944-4086
• Location Navy Pier, 600 E. Grand Avenue, Chicago, IL 60611
• Neighborhood River North (Chicago)
• Cross street Lake Shore Drive
• Parking details Public parking is located in an 1800-space lot on Navy Pier, directly across from Mystic Blue Cruises. In the event the Navy Pier parking lot is filled to capacity, a number of nearby lots (3-4 blocks west) offer convenient parking. We suggest allowing an additional 30-minutes to park during the summer, weekends & holidays as space is limited.
• Public transit The CTA provides seven bus lines with more than 200 buses serving Navy Pier daily. These are #29 State St, #65 Grand Ave, #66 Chicago Ave. and the #124 Navy Pier Express.During weekday rush hours, the #2 Hyde Park Express (stops running at 9:10pm), #120 Northwestern/Wacker Express and the #121 Union/Wacker Express (stops running at 10:00pm).
• Entertainment DURING BOARDING: Light music played dockside will help you unwind. AFTER LEAVING THE DOCK: Your DJ will create a chill yet energizing atmosphere with popular music suited to your cruise, setting the tone for a night of dancing on beautiful Lake Michigan. WHILE DINING: Our cruise host will mingle with guests and celebrate everyone’s special occasion. Our rooftop lounge is the perfect place to relax with some light music and take in the world-famous Chicago skyline.
• Additional Banquet, Beer, Dancing, Entertainment, Full Bar, Late Night, Outdoor Smoking Area, Patio/Outdoor Dining, Private Room, View, Weekend Brunch, Wheelchair Access

Plated menu included on standard dinner cruises

Optional - for additional charge

Shrimp Cocktail

Sriracha Cocktail Sauce

Seafood Tower

Maine Lobster | Alaskan King Crab | Jumbo Shrimp | Bay Scallop Ceviche | Sriracha Cocktail Sauce | Parsley Aioli

First Course

Wedge salad.

Applewood Smoked Bacon | Sun-Dried Tomatoes | Chives & Italian Parsley | Buttermilk Ranch Dressing

Lobster Soup

Brioche Croutons | Chives

Smoked Moulard Duck Breast

Cranberry, Cherry & Caramelized Shallot Compote | Pickled Cornichons & Pearl Onions

Jumbo Lump Crab Cakes

Sweet Corn, Red Bell Pepper & Thyme Succotash | Cajun Cream Sauce

Oven Baked Atlantic Salmon Filet

Lemon Orzo with Red Onions & Sun-Dried Tomatoes | Citrus Dill Sauce

Maple & Mustard Glazed Chicken Breast

Fingerling Potatoes & Chives | Haricot Verts | Dijon Mustard Cream Sauce

Braised Beef Short Rib

Idaho Potato & Horseradish Mash | Baby Carrots | Pearl Onions & English Peas | Cabernet Sauvignon Sauce

Greek Zucchini Fritters

Lemon Orzo with Red Onions & Sun-Dried Tomatoes | Spring Onion & Cucumber Tzatziki

Filet Mignon & Lobster Tail

(for additional charge) Truffle Potatoes | Glazed Baby Carrots | Herb Butter

Duo of Sorbet

Seasonal Sorbet | Fresh Fruit

Granny Smith Apple Parfait

Cinnamon Spiced Apples | Almond & Oat Crumble | Candied Chili Bacon

Salted Caramel Cake

Dark Chocolate Ganache | Raspberry Sauce

Odyssey Signature Warm Butter Cake

Vanilla Bean Ice Cream | Blackberry Sauce

Plated menu included on Prix Fixe Dinner Cruises

Entrée Choices

Lemon Orzo with Red Onion & Sun-Dried Tomatoes | Citrus Dill Sauce

Odyssey Signature Dessert Station

Mini Pastry Cups | Cakes | Pastries | Seasonal Fruit

What 19 people are saying

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• 4.2 Service
• 4.4 Ambience

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How is Odyssey Cruises Lake Michigan restaurant rated?

Odyssey Cruises Lake Michigan is rated 4.2 stars by 19 OpenTable diners.

Navy Pier, 600 E. Grand Avenue, Chicago, IL 60611

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Opening for the Season: May 17th, 2024! Click to book your next sail on board Tall Ship Windy!

Tall Ship Windy

The official flagship of the city of chicago chicago skyline sails & tours.

Initial Public Offering Announcement

AMDI plans to conduct its initial public offering (IPO) through the New York Stock Exchange American with the symbol ‘AMDI’ through its underwriter, Kingswood Investments, a division of Kingswood Capital Partners, LLC (or Kingswood), which is acting as the sole representative of the underwriters. AMDI anticipates a public offering price between $3.50 to $4.50.

AMDI is a maritime tour activity and attractions operator with the following wholly-owned operating units: Seas the Day Charters in the U.S. Virgin Islands, Tall Ship Windy in Chicago, Illinois and Paradise Adventures in Panama City Beach, Florida. The Company plans to use the proceeds of its IPO to acquire Paradise Yacht Management and Charter Smarter in the U.S. and British Virgin Islands and the Bahamas.

Interested parties may subscribe to the IPO or obtain a prospectus and more information at  Webull .

You may also obtain the Company’s prospectus and other information at the  SEC website .

Join us for Opening Weekend May 17 – May 19, 2024!

Tall Ship Windy offers an unforgettable sailing experience. Explore Chicago’s Skyline and choose from Sunset Sails, Skyline Sails and Educational Sails.

Sail in Florida and the Virgin Islands!

Thank you for another fantastic season! We’re already counting down the days until we can set sail with you again aboard Tall Ship Windy in 2024.

If you’re looking for other ways to sail, we invite you to explore our other exciting locations! Tall Ship Windy is proud to be a part of the Amphitrite Digital family of companies.

Join us at Paradise Adventures in Panama City Beach, Florida, where sun-kissed shores await. If you’re dreaming of a week-long yacht vacation, Charter Smarter in the Virgin Islands promises an unforgettable experience. For a full or half day on the water from St. Thomas and St. John in the US Virgin Islands, our team at Seas the Day Charters USVI is ready to make your dreams a reality.

No matter where your compass points, we’re here to create more unforgettable memories with you. Until then, fair winds and following seas.

Paradise Adventures Catamarans and Watersports

Enjoy top-rated boating adventures on the Florida Gulf Coast at Paradise Adventures Catamarans and Watersports!

• Experience inflatable fun on a Privateer Adventure Tour
• Snorkel and explore Shell Island
• Look for dolphins on a Sightseeing Tour or enjoy a Breathtaking Sunset Sail
• Book a private charter on a catamaran, sailboat, powerboat or pontoon boat

Learn more about Paradise Adventures

Charter Smarter

Explore the wonders of the Virgin Islands with an all-inclusive Charter Smarter yacht charter!

• Each week-long adventure includes a professional captain, a skilled chef and all meals and drinks
• Take advantage of all your catamaran’s amenities, water toys and land-based activities in paradise
• Bring your family or friends and create memories that will last a lifetime

Learn more about Charter Smarter

Seas the Day Charters USVI

Enjoy a full or a half-day adventure with Seas the Day Charters USVI!

• Luxury sailing excursions & fast powerboat adventures
• Private & semi-private charters available
• Snorkel with beautiful fish, coral and sea turtles and explore white sandy beaches
• Explore the US Virgin Islands or the British Virgin Islands

Learn more about Seas the Day Charters USVI

Chicago Skyline Sail

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

Hour Glass 75 Minutes | Starting at $39

• Hour Glass 2 Hours

Monday Night Blues Summer Concert Series

Kick-off your week and join us for a 2-hour concert sail from 7pm-9pm every Monday this summer. 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 blues.

• Hour Glass 90 minutes

Fireworks Cruise! 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.

Chicago’s Famous Friday Night Pirates Pub Sail

Sail into the night and embark on a two-hour party sail; join us for Chicago’s only Pirates Pub. Sail onboard a 148-foot Tall Ship in the Windy City! This is an event you will not want to miss. Enjoy an onboard DJ and the wind in your hair as you dance the night away with the mesmerizing Chicago skyline as your backdrop. Sing along to traditional pirate tunes and your favorite party anthems while soaking in the breathtaking sights of Lake Michigan.

• Great for Children!

Educational Sail: Tall Ship Discovery Sail

History comes alive on this exciting educational adventure for curious minds of all ages. Experience a hands-on sailing trip aboard Windy led by our crew-educators.

Choose a Sailing Category

Fireworks sails, special event sails, welcome aboard tall ship windy.

The Tall Ship Windy, located on Chicago’s Navy Pier, brings you exciting boat tours that are educational, creative, and inspiring. From our daily storytelling adventures and field trips for students to our concert sails, there is something for everyone. Come enjoy the Chicago skyline as you sail on our tall ship!

For groups or charters, email us at [email protected] or call us at: (312) 451-2700

The Tall Ship Windy offers the most spectacular fireworks experience during the Chicago summer.

Our sails are both fun and educational, which makes them the perfect way to see Lake Michigan.

Feel the spirit of centuries past and hoist the sails as part of your experience on Tall Ship Windy.

There is simply no better way to experience Chicago’s world-famous skyline than on the Tall Ship Windy.

Have a special event coming up?

Catch these five-star reviews from tripadvisor.

We went on the "pirate" cruise. They told tales of actual Lake Michigan pirates and made it very entertaining for the kids and the adults. I want to go on this cruise again!

We went on the Lakeside Architecture Tour. It was a very educational and relaxing seventy-five minutes. I highly recommend the experience.

I've set sail on Tall Ship Windy 4-5 times over the past few years, and it is always a good time. You get a nice view of the city and the crew is entertaining and knowledgeable.

If you want humor, entertainment, and an inclusive experience for young and the old, don’t miss this! I appreciate everything about this adventure, and Austin you’re the best!

Had a wonderful sail on a chilly, overcast night! Crew was professional, friendly and informative. Would recommend this trip to anyone, so relaxing. Oh, used a Groupon, an extra bonus!

Best view of the city! Highly recommend the 7pm sail to watch the sunset between the buildings. Fun and knowledgeable crew made the Windy the highlight of our Chicago visit.

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Go Visit Chicago Let's Discover the Windy City

Chicago odyssey dinner cruise.

Victor Blog , Boat Tours , Fireworks Cruises , Night Cruises , Tours Leave a comment

Chicago Odyssey Dinner Cruise - One of the best night cruises in Chicago. Excellent views of Chicago skyline at night, plus you can take advantage of fireworks show in summer season.

Chicago Odyssey Dinner Cruises on Lake Michigan

The Chicago Odyssey Dinner Cruise takes you along the Lake Michigan and offers unmatched views of the world-famous Chicago skyline. This 3 hours long tour is not to be missed even if you visit Chicago for a very short duration of time.

• 3-hour Chicago dinner cruise
• A distinctive 3-course dinner that has been freshly prepared
• A live band to provide on board entertainment
• Views of the world famous Chicago skyline
• Cruise along the Chicago Lakefront for exceptional views and attractions of Chicago like the Willis Tower, the John Hancock, the Shedd Aquarium and Aon Center.

View Pricing and Availability

To enjoy the Chicago Odyssey Dinner Cruise in the best possible manner, arrive well before the departure time and dress in your most festive attire. You get to enjoy the electric atmosphere of Navy Pier, alive with entertainers and remarkable views. These Chicago dinner cruises on Lake Michigan are operated by top dinner cruise lines including  Spirit of Chicago Dinner Cruise and Odyssey dinner cruise Chicago .

As soon as you step aboard, the Captain and crew will greet you and the ship’s photographer will record the moment. When you reach the deck, you are greeted by your host and escorted to a private table. Now the waiting staff will introduce themselves and the experience begins.

There are three climate-controlled dining decks featuring a unique setting with understated Art Deco accents, which is reminiscent of the classic ocean liners. One of the highlights is visiting Captain’s bridge, which is open to all passengers throughout most of the cruise.

The menu is truly creative and appetizing consisting of seasonal hors d’oeuvres, appetizers, entrees and desserts and is freshly prepared on-board daily. The wine list is absolutely impressive and the entire experience is enhanced further by the presence of soft piano music and spacious dance floors with live music provided by a five-piece band.

The entertainment continues until well after the ship returns to the pier. This dinner cruise is perfect to enjoy an unforgettable evening of great food and great music.

Chicago Fireworks Dinner Cruise

During summer season, you can even choose to upgrade your Chicago Dinner Cruise to include a spectacular fireworks display on Wednesdays and Saturdays. You get the opportunity to witness the spectacular show from the decks of the ship as the gorgeous sky is all lit up at night.

Chicago Odyssey Dinner Cruise Schedule Details

Chicago Dinner Cruise

Departure Point: Cruise departs from the south side of Navy Pier

Departure Time: Sunday: 6:30pm Monday-Thursday: 7pm Friday, Saturday, Sunday – 7:30pm

Boarding on Chicago odyssey dinner cruise begins one hour prior to above times. All departure times are subject to change

Duration: 3 hours (approx.)

Additional Information

Inclusions:

• Three-hour dinner cruise
• Three-course dinner with coffee, tea and iced tea
• Service charges
• Local Taxes and fees

Exclusions:

• Alcoholic drinks (available to purchase)
• Confirmation is subject to availability and will be received within 48 hours of booking
• All interior areas of the ship are non-smoking. Guests who smoke may do so on the outdoor observation decks only.  

Chicago Fireworks Cruises

View the spectacular 30-minute pyro-musical program fireworks display with the world famous Chicago Skyline as a backdrop for your unforgettable evening. If you are looking for something for Sunday brunch, then I also recommend you Sunday brunch cruise on Lake Michigan .

Firework Schedule from June 1 – August 31

• Wednesday 9:30 pm
• Saturday 10:15 pm

Dress Code :

It is strictly recommended that men dress up in jackets and women in cocktail attire.

The cruise does not permit wearing of jeans, shorts, tank tops or halter tops.

Itinerary :

SAMPLE MENU: (subject to change)

********************************************* First Course

• Caramelized Duck en Croûte: Duck Confit, Forest Mushrooms, Sage and Monterrey Jack Cheese baked in a Puff Pastry, served over Spaghetti Squash, with Dried Cherries, Candied Pecans and drizzle of Marsala Wine Demi-glace
• Mixed Greens with Apples and Strawberries Fresh salad Greens tossed with Granny Smith Apples, Caramelized Pecans, Strawberries, Grape Tomatoes and crumbled Bleu Cheese, in a Raspberry Vinaigrette
• Lobster Bisque: Lobster simmered in sweet cream Butter and blended with Sherry and Crème Fraiche, served with an herbed Crouton
• Seafood Mélange Fresh Atlantic Sea Scallops, Gulf Shrimp and Blue Crab baked with Peppers and Dijon into a cake, accompanied with toasted Crostini

********************************************* Main Course

• Maple-Glazed Chipotle Chicken: Pan-roasted Smoked Chicken Breast, served with a fiery Vegetable Ratatouille and roasted Yukon Gold Potatoes, topped with a Chipotle Tomato Cream
• Argentinean Salmon: Pan-seared fresh Salmon fillet marinated in spicy Chimichurri Sauce, served over a fried mashed Yucca Cake, topped with a sweet Corn Posole and crispy Corn Tortilla Strips
• Seafood Ravioli Gratinee: Jumbo Ravioli filled with imported Italian Cheeses, topped with Gulf Shrimp, Bay Scallops, and a rustic Pomodoro Sauce
• Mushroom Braised Short Ribs: Braised Beef Short Ribs marinated in a Shallot and Wild Mushroom Gravy, served with Garlic Mashed Potatoes, Puff Pastry and crispy Onion Straws
• Roasted Vegetable Napoleon: Ragoût of Tomato, Zucchini, Eggplant and Summer Squash, layered with a White Bean Purée between crispy Lavash, served with a fresh Basil Marinara

********************************************* Desserts

• New York Style Cheesecake Traditional rich Cheesecake atop a seasonal Glaze
• Decadent Chocolate Truffle Torte Rich two layer moist Cake filled with a delicate Chocolate Mousse fully enrobed in a smooth Dark Chocolate Ganache
• Bread Pudding Baked with Dried Currants, Cranberries and Coconut, served warm with Vanilla Bean Ice Cream sprinkled with Toasted Coconut
• Peach and Blueberry Crisp Fruit Crisp served warm with Vanilla Bean Ice Cream and a light Blueberry Purée

Terms and Conditions :

All sales are final and incur 100% cancellation penalties.

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Spirit of Navy Pier – City Cruises

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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!

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Cruising the Moskva River: A short guide to boat trips in Russia’s capital

There’s hardly a better way to absorb Moscow’s atmosphere than on a ship sailing up and down the Moskva River. While complicated ticketing, loud music and chilling winds might dampen the anticipated fun, this checklist will help you to enjoy the scenic views and not fall into common tourist traps.

How to find the right boat?

There are plenty of boats and selecting the right one might be challenging. The size of the boat should be your main criteria.

Plenty of small boats cruise the Moskva River, and the most vivid one is this yellow Lay’s-branded boat. Everyone who has ever visited Moscow probably has seen it.

This option might leave a passenger disembarking partially deaf as the merciless Russian pop music blasts onboard. A free spirit, however, will find partying on such a vessel to be an unforgettable and authentic experience that’s almost a metaphor for life in modern Russia: too loud, and sometimes too welcoming. Tickets start at $13 (800 rubles) per person.

Bigger boats offer smoother sailing and tend to attract foreign visitors because of their distinct Soviet aura. Indeed, many of the older vessels must have seen better days. They are still afloat, however, and getting aboard is a unique ‘cultural’ experience. Sometimes the crew might offer lunch or dinner to passengers, but this option must be purchased with the ticket. Here is one such  option  offering dinner for $24 (1,490 rubles).

If you want to travel in style, consider Flotilla Radisson. These large, modern vessels are quite posh, with a cozy restaurant and an attentive crew at your service. Even though the selection of wines and food is modest, these vessels are still much better than other boats.

Surprisingly, the luxurious boats are priced rather modestly, and a single ticket goes for $17-$32 (1,100-2,000 rubles); also expect a reasonable restaurant bill on top.

How to buy tickets?

Women holding photos of ships promise huge discounts to “the young and beautiful,” and give personal invitations for river tours. They sound and look nice, but there’s a small catch: their ticket prices are usually more than those purchased online.

“We bought tickets from street hawkers for 900 rubles each, only to later discover that the other passengers bought their tickets twice as cheap!”  wrote  (in Russian) a disappointed Rostislav on a travel company website.

Nevertheless, buying from street hawkers has one considerable advantage: they personally escort you to the vessel so that you don’t waste time looking for the boat on your own.

Prices start at $13 (800 rubles) for one ride, and for an additional $6.5 (400 rubles) you can purchase an unlimited number of tours on the same boat on any given day.

Flotilla Radisson has official ticket offices at Gorky Park and Hotel Ukraine, but they’re often sold out.

Buying online is an option that might save some cash. Websites such as  this   offer considerable discounts for tickets sold online. On a busy Friday night an online purchase might be the only chance to get a ticket on a Flotilla Radisson boat.

This  website  (in Russian) offers multiple options for short river cruises in and around the city center, including offbeat options such as ‘disco cruises’ and ‘children cruises.’ This other  website  sells tickets online, but doesn’t have an English version. The interface is intuitive, however.

Buying tickets online has its bad points, however. The most common is confusing which pier you should go to and missing your river tour.

“I once bought tickets online to save with the discount that the website offered,” said Igor Shvarkin from Moscow. “The pier was initially marked as ‘Park Kultury,’ but when I arrived it wasn’t easy to find my boat because there were too many there. My guests had to walk a considerable distance before I finally found the vessel that accepted my tickets purchased online,” said the man.

There are two main boarding piers in the city center:  Hotel Ukraine  and  Park Kultury . Always take note of your particular berth when buying tickets online.

Where to sit onboard?

Even on a warm day, the headwind might be chilly for passengers on deck. Make sure you have warm clothes, or that the crew has blankets ready upon request.

The glass-encased hold makes the tour much more comfortable, but not at the expense of having an enjoyable experience.

Getting off the boat requires preparation as well. Ideally, you should be able to disembark on any pier along the way. In reality, passengers never know where the boat’s captain will make the next stop. Street hawkers often tell passengers in advance where they’ll be able to disembark. If you buy tickets online then you’ll have to research it yourself.

There’s a chance that the captain won’t make any stops at all and will take you back to where the tour began, which is the case with Flotilla Radisson. The safest option is to automatically expect that you’ll return to the pier where you started.

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