Sailing in Magnificent Mile, Chicago


One or Two Three-Hour Introductory Sailing or Racing Lessons from 3rd Coast Cruising (Up to 68% Off)

3rd Coast Cruising

DuSable Harbor

$189 for two three-hour introductory sailing or racing lessons ($600 value).

$300 $99

$449 for the "Fundamentals of Sailing" Course from Celestial Sails ($1,000 Value)

Celestial Sails

31st Street Harbor

Professional sailors offer an introductory course to sailing that takes place on 44-foot yacht.

$1,000 $449

One, Three, or Five Three-Hour Sailing Lessons at Sailboat-X.

Sailboat-X.com

Chicago

US Sailing–certified instructors teach students to rig the boat and take the helm on a 33-foot vessel.

$125 $66

Navy Pier Sailing Cruises at Celestial Sails (Up to 57% Off)

Celestial Sails

31st Street Harbor

Three-Hour Sailing Charter (Two People).

$550 $249

Private Lakefront Sailing Tours with Windy City Sailing (Up to 30% Off)

Windy City Sailing

North Side

Private Lakefront Sailing Tour: Monday - Friday .

$600 $425

$149 for Soaring Flight Orientation and 3,000 Foot Sail Plane Ride at Sky Soaring Glider Club ($299 Value)

Sky Soaring Glider Club

Hampshire, IL

2-seat glider soars 3,000 ft above Hampshire countryside while commercial pilot mans controls

$299 $149

Two-Hour Private Cruise for Up to 6 from New Buffalo Sailing Excursions (Up to 45% Off).

New Buffalo Sailing Excursions

New Buffalo

Here are some things to know about the sailing excursions.

$300 $169

Sublime with Rome & The Offspring on Friday, September 8, at 7 p.m.

Sublime with Rome & The Offspring

Huntington Bank Pavilion at Northerly Island

Sailing into the mainstream:.

$76.15 $45

Two or Three-Hour Pontoon Boat Rental for eight or 12 with Chicago Boat Rentals (Up to 56% Off)

Chicago Boat Rentals

Goose Island

Boat rental service specializes in providing pontoons for eight or 12 that can be driven by guests with a few minutes’ training

$300 $139

3-Hour Party-Boat Rental with Optional Fireworks for Up to 10 People from Island Party Boat (Up to 58% Off)

Island Party Boat

Downtown

Clients and their families or friends can experience an enjoyable day or night out on the water, topped by an optional fireworks show.

$616 $259

Three-Hour TikiBoat Cruise with a Crew at Chicago TikiBoat (Up to 60% Off)

Chicago TikiBoat

Monroe Harbor

Groups of up to 12 and a licensed captain hit the lake on a boat with a water slide, grill for barbecuing, and float rafts for lounging

$780 $315

Two-Hour Electric or Pontoon Boat Rental for up to Twelve People at Vantage Boat Share (Up to 50% Off)

Vantage Boat Share

Chicago

Boaters discover the beauty of Chicago’s local waterways surrounding the city during their boating experience

$200 $99

Two- or Three-Hour Boat Rental for Up to Six People from Chicago Adventure, Inc (Up to 45% Off)

Chicago Adventure, Inc

Burnham Harbors

Groups of up to six cruise the waters of Lake Michigan in a sleek Carver 350 Mariner yacht during two- or three-hour rentals

$740 $499

Three or Four-Night Cabin Stay and Daily Boat Rental for Two People at Gold Mine Camp (Up to 64% Off)

Gold Mine Camp

Gold Mine Camp

Explore the Vermilion River, the lake, and the wilderness of Northern Minnesota

$630 $229

One Booze Cruise Ticket for April 15, April 21, or April 28 at Yacht Party Chicago (Up to 50% Off)

Yacht Party Chicago

Boarding at DuSable Harbor

For up to three hours aboard a luxury yacht, guests dance as a DJ plays music; at some special events, fireworks explode overhead

$50 $25

Lake Michigan and Chicago River Architecture Cruise by Speedboat

Entertainment Cruises

Chicago

$42.87 $42.87

Semi-Private 3-Hour Sunset Cruise for Up to 4 or 6 People from 3rd Coast Cruising (Up to 56% Off)

3rd Coast Cruising

DuSable Harbor

For three hours, you can cruise along Lake Michigan with a group of up to 5 friends as the sun sets in the distance

$900 $500

Pontoon or Runabout Rentals at SkipperBud's (Up to 51% Off)

SkipperBud's

Multiple Locations

Renters check in and experience an exciting, memory-filled day on the water with friends and family

$395 $195

$270 for a Two-Day Advanced Adventure Scuba Course with Five Dives from Dive Right In Scuba ($499 Value)

Dive Right In Scuba

Plainfield

Certified instructors who train police and fire department dive teams teach advanced scuba techniques during dives at a local quarry

$499 $270

BYOB Three-Hour Scenic Sailing Cruise for One, Two, Four, or Six at Sailboat-X (Up to 54% Off)

Sailboat-X.com

Chicago

Three-Hour Scenic Sailing Cruise for One.

$125 $66

Private Fireworks Cruise

Come Sailing, Inc.

Chicago

Boarding any sailboats operated by Come Sailing, Inc.

$389.76 $389.76

Private Day Sailing on Lake Michigan

Come Sailing, Inc.

Chicago

Boarding any sailboats operated by Come Sailing, Inc.

$389.76 $389.76

Private Morning Sail on Lake Michigan

Come Sailing, Inc.

Chicago

Furthermore, by boarding any of our sailboats you are granting Come Sailing, Inc.

$389.76 $389.76

Lake Michigan Speedboat Ride

Entertainment Cruises

Chicago

$27.79 $27.79

3- or 5-Hour Party Bus Rental for 25 Passengers from Party Bus Hoppers (Up to 67% Off)

Party Bus Hoppers

Chicago

Passengers cruise in high style to events on a party bus that can seat up to 25 passengers

$1,100 $399

$6 for Two Murder Mystery Party Games of Your Choice from Clean Murder Mysteries ($12 Value)

Clean Murder Mysteries

Online Deal

Add an extra element of suspense to any party – band together and solve the mystery before time runs out

$12 $6

Party-Bus Rental or SUV Transportation from Rokstars Chicago (Up to 46% Off). Four Options Available.

Rokstars Chicago

Chicago

Celebrate any occasion with up to 24 people on a rented party bus for three, four, or five hours, or get where you need to go in an SUV

$900 $499

Jimmy Buffett and Huey Lewis All-Inclusive Rooftop Experience on Saturday, July 15 at 7 p.m.

Jimmy Buffett and Huey Lewis

Skybox on Sheffield Rooftop

Legendary singer-songwriter behind “Margaritaville” joins forces with iconic pop-rocker of “The Power of Love” fame

$195.51 $99

All-Inclusive Rooftop View of Florida Georgia Line, Backstreet Boys, and Nelly at Wrigley Field on Saturday, August 12

Florida Georgia Line, Backstreet Boys, and Nelly

Skybox on Sheffield

Enjoy rooftop views while singing along to hits such as “This Is How We Roll,” “I Want It That Way,” and “Hot in Herre”

$222.39 $159

All-Inclusive Florida Georgia Line, Backstreet Boys, and Nelly Concert Rooftop Ticket on Saturday, August 12

Florida Georgia Line, Backstreet Boys, and Nelly

Lakeview Baseball Club

Country-pop duo deliver chart-topping hits like “Cruise” and “This Is How We Roll;” Backstreet Boys and Nelly join

$222.39 $169

Select Local Merchants

  • Pinnacle Yachts
    Put your cares aside and sail away at Pinnacle Yachts in Chicago. Whether you're looking for a quick snack or a full meal, the restaurant at this center is sure to dish out something delicious. Don't leave the kids at home — youngsters will love the family-friendly activities at this center just as much as mom and dad. Parking is plentiful, so patrons can feel free to bring their vehicles.
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    Chicago, IL US
    +13128960777
  • SideTour - Leisure
    Chicago's SideTour - Leisure is a great place to stop in for some fun. Beginners and experts alike are invited to practice hot yoga at SideTour - Leisure, but be prepared for an ultimate workout. Aerial yoga will help you work out your inner core. Ready, set, go! Navigate the field at SideTour - Leisure but remember to throw on some safety gear before the paintballing begins. Parking is plentiful, so visitors can feel free to bring their vehicles. SideTour - Leisure is obviously the place to be, so get your calendar out and make plans to visit it soon.
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    Chicago, IL US
  • Chicago First Lady
    The history buffs of Chicago's Finest Tours lead engaging and dynamic tours of two very different parts of the city. During the summer, intimate groups of up to 20 traverse the various walkways of the bustling yet majestic riverfront or climb aboard a boat for a sunny river voyage, soaking in vistas of Chicago's many architectural wonders. In the winter, tourgoers head below the sidewalks with torch in hand to explore the troll-populated tunnels of the Pedway, Chicago's underground network of shops, hotels, train stations, and eateries. Regardless of the tour, the knowledgeable guides engage strollers in a two-way conversation about the Windy City, enlightening audiences with historical yarns and humorous anecdotes.
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    Chicago, IL US
    +18473581330
  • SideTour - Leisure
    Switch up your normal routine and head to SideTour - Leisure in Chicago and experience something new. Yogis of all experience levels can enjoy a fun and adventurous aerial yoga class. Who's ready to play some paintball? Color yourself silly at SideTour - Leisure and let the games begin! Heat things up (and sweat out the impurities) with SideTour - Leisure's hot yoga classes. Parking is plentiful, so patrons can feel free to bring their vehicles. SideTour - Leisure is sure to be a fun experience for the whole family!
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    Chicago, IL US
  • SideTour - Leisure
    SideTour - Leisure is Chicago is a place where the fun doesn't stop. Ready, set, go! Navigate the field at SideTour - Leisure but remember to throw on some safety gear before the paintballing begins. It's about time you took advantage of their low-impact but exhausting aerial yoga. Join hot yoga enthusiasts at SideTour - Leisure and open up your mind, body (and pores) to a healthier lifestyle. Parking is plentiful, so guests can feel free to bring their vehicles. If you're ready to try something new, come to SideTour - Leisure!
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    Chicago, IL US
  • Chicago Line Cruises
    Sometimes all it takes is a suggestion. Terry Johnson and Paul McCarthy founded their vessel-chartering business in 1980. But when a good friend recommended they offer expertly narrated tours on the history and the iconic architecture of Chicago, the pair jumped at the opportunity. Praised as the “Best architecture tour available” by the Chicago Sun-Times and “Most engaging tour of the bunch” by Time Out Chicago, their river cruises take passengers on three types of educational, 90-minute tours of the city. Chicago Line Cruises has transported more than three million Chicagoans and visitors along the river for entertainment, stunning views, and a deeper appreciation for architectural design. Architectural Cruises Learn how Chicago became the birthplace of the first buildings to be dubbed "skyscrapers." Hear how the Great Chicago Fire paved the way for an architectural renaissance. See a broad selection of modern architectural styles and discover the distinctive characteristics of each. Experience Chicago's first architectural river cruise. Historical Cruises Hear the overarching story of how Chicago transformed from a swampy marshland to a world-class city. Learn about the Chicagoans whose innovations helped influence architecture and commerce around the world. Savor a cup of Starbucks coffee while a guide recounts Chicago's triumphant and tragic moments. Historical tours are presented in partnership with the Chicago History Museum. Chartered Cruises Private outings are available for 20–173 passengers. Full-service bars and professional sound systems are available for special events. Celebrate while savoring views of the Chicago skyline from a different perspective. Choose from three vessels: the Ft. Dearborn, the Innisfree, and the Marquette.
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    Chicago, IL US
    +13125272002
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