Sailing in Summit, IL


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

Sailboat-X.com

Multiple Locations

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

$250 $132

Three-Hour BYOB Cruise or Four-Hour BYOB Fireworks Cruise for Up to Six from Celestial Sails (UP to 64% Off)

Celestial Sails

31st Street Harbor

Explore Lake Michigan aboard a 44-foot Beneteau Oceanis yacht; fireworks cruises include choice views of Navy Pier pyrotechnics

$250 $99

2.5-Hour Private, Hands-On Sailing Experience for Up to Six from Smelly Onion Sailing (Up to 41% Off)

Smelly Onion Sailing

Burnham Harbors

Private, hands-on sailing experience lets guests take over the role of the crew and sail the boat; captains teach them basic skills

$550 $325

$49 for a Mid-Day, Happy Hour, or Sunset Cruise for Two from Nauti Cat Cruises (up to an $80 Value)

Nauti Cat Cruises

Traverse City

Atop the largest commercial sailing catamaran on the Great Lakes, passengers take in the beautiful views and enchanting scents of the bay

$80 $49

Spirit Ships and Haunted Harbors of Chicago

Windy of chicago Inc, DBA: Tall Ship Windy

Chicago

$33.60 $33.60

Pontoon-Boat Rental for 8 or 12 from Corporate Tailgate Boat Rental (Up to 56% Off). Three Options Available.

Corporate Tailgate Boat Rentals-Chicago

Chicago

Pontoon boats cruise leisurely up and down the Chicago River on a waterfront tour; see Navy Pier fireworks; bring your own food and drinks

$300 $139

Two-Hour 21-Ft Electric or 22-Ft Pontoon Boat Rental for Up to 12 People from Vantage Boat Share (Up to 67% Off)

Vantage Boat Share

Vantage Boat Share

Luxury 21-foot electric boats or 22-foot pontoon boats host up to 12 guests in two-hour tours of area waterways

$250 $99

Two- or Three-Hour Boat Rental for Up to Six from Chicago Adventure Club (Up to 39% Off)

Chicago Adventure Club

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

Lake Michigan and Chicago River Architecture Cruise by Speedboat

Entertainment Cruises

Chicago

$39.38 $39.38

$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

Lake Michigan Speedboat Ride

Entertainment Cruises

Chicago

$25.46 $25.46

Full-Day SUP or Kayak Rental at Mill Race Cyclery (50% Off). Four Options Available.

Mill Race Cyclery

Geneva

Renters can choose to cruise the Fox River atop a stable standup paddleboard or sitting on a single-person or tandem kayak

$50 $30

Roller-Skating for Two, Four, or Six with Skate Rentals at Fleetwood Roller Rink (48% Off)

Fleetwood Roller Rink

Summit

Couples or groups boogie around the glass-smooth surface of this 75'x165' hard-maple rink on included rental skates

$22 $12

Admission for Two Adults, Family Pack, or Four-Day Family Pass at Pumpkin Patch Festival (Up to 81% Off)

Pumpkin Patch Festival

Summit

Celebrate all things autumn at Pumpkin Patch Festival, which features a pumpkin patch, petting zoo, carnival rides, food and pony rides

$30 $15

Groupon Exclusive: Free 45-Day Subscription to Hulu’s Limited Commercials Plan

Hulu

Online Deal

Unlimited instant streaming service offers a 45-day trial period to test out its content, which includes popular network TV shows and movies

$11.98 $0

$5 for a Movie Ticket at Studio Movie Grill ($10.75 Value)

Studio Movie Grill

Wheaton

A wide selection of new releases and cult classics is projected on towering screens as viewers watch from leather recliners and tables

$10.75 $5

Amusement-Parks Package for Two or Four from Haunted Trails Amusement Park (55% Off). Two Locations Available

Haunted Trails Amusement Park

Multiple Locations

Visitors enjoy game rooms and attractions like mini golf, go-karts, and jr. karts at both locations, plus laser tag at the Joliet location

$55.20 $26

Amusement-Park Package with Attractions and Tokens for Two or Four at Enchanted Castle (Up to 55% Off)

Enchanted Castle

Lombard

Guests enjoy an afternoon of fun with attractions such as bumper cars, go karts, and laser tag, plus tokens for the game room

$55.20 $26

Roller Skating with Skate Rentals for Two, Four, or Six at Lombard Roller Rink (Up to 52% Off)

Lombard Roller Rink

Lombard

Fun and inventive approaches to roller skating, including Family Night, 21+ events, and sessions set to the tune of R&B or organ music

$24 $12

Farm Admission for Two or Six at Odyssey Fun Farm (Up to 44% Off)

Odyssey Fun Farm

Odyssey Fun Farm

110-acre farm with corn mazes, hayrides, pumpkin patch and petting zoo, along with kids’ zone with inflatable slides and castles

$24 $14

Halloween Booze Cruises (And Saturday Night Cruises) on Lake Michigan from Yacht Party Chicago (Up to 50% Off).

Yacht Party Chicago

Chicago

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

$50 $35

Weekend Corn Maze and Fall Activities for Two, Four, or Six at Keller's Farmstand (Up to 52% Off)

Keller's Farmstand

Oswego

This family-run farmstand celebrates fall with a 12-acre corn maze, hayrides, an animal barn, and a play area

$18 $10

Visit to Chicago Toy & Game Fair at Navy Pier on November 19 or 20 (Up to 53% Off). Three Options Available.

Chicago Toy & Game Fair

Navy Pier

Two-day fair to play with toys and games from around world, meet inventors, enjoy interactive exhibits and stage events.

$23 $12

Fast Pass Admission for One or Two to HellsGate Haunted House (Up to 44% Off)

HellsGate Haunted House

Hells Gate Haunted House

Visitors can scare themselves silly at this intense haunted house while using a Fast Pass to shorten their wait and skip the lines

$35 $20

Movie with Popcorn and Drinks for One, Two, or Four at Village of Bensenville (Up to 50% Off)

Village of Bensenville

Bensenville

Guests grab buckets of popcorn and large sodas before heading into intimate twin theaters to view recent releases

$44 $22

$6 for Credit Towards First Three Rides ($8x3) from Uber for New Customers

Uber

Online Deal

Through the use of a free-to-download mobile app, this ride-service connects you with a driver in real time to take you where you need to go

$24 $6

Ice Skating with Skate Rental for Two or Four at Rocket Ice Arena (Up to 55% Off)

Rocket Ice Arena

Bolingbrook

Skaters of all levels hone their moves during open skates while supporters cheer them on from lodge with fireplace, free WiFi & café

$40 $18

Two Hours of Bowling with Shoe Rental for Six at Burr Oak Bowl (62% Off)

Burr Oak Bowl

Burr Oak Bowl

Spend two hours aiming for strikes on a gleaming lane with your friends

$62.50 $24

Admission for One, Two, or Four to the Illinois Railway Museum (Up to 50% Off)

Illinois Railway Museum

Evergreen Park

Watch restored antique train cars in operation, then check out memorabilia from the Chicagoland and national rail industries

$14 $8

50 Shades Male Revue Show on Friday, October 7 and Saturday, October 8

50 Shades Male Revue Show

Stereo Nightclub

Male dance revue comprised of muscle bound hunks excite crowds with sensual moves and Vegas showmanship. Excellent for a ladies night out

$32.64 $15

Select Local Merchants

  • Go Sailing Chicago
    Gliding across Lake Michigan, the sailing party watches the sun sink beneath the Chicago skyline. As the last rays fade from view, the city's skyscrapers throw their light onto the lake's surface. The captain steers the ship past Grant Park and Millennium Park, and then veers out toward Navy Pier, where the ship's passengers find a prime viewing spot for the Saturday-night fireworks show. In addition to charters like these, the captains of Go Sailing Chicago—all holding US Coast Guard Master Captain licenses and certifications from the American Sailing Association and US Sailing—furnish beginner through advanced sailors with sailing gloves and life jackets before leading hands-on instruction in proper seamanship. Launching from DuSable and Monroe Harbor, and sometimes other points along the lakeshore, Go Sailing Chicago's four-boat fleet meets or exceeds the safety standards set down by the USCG and the most persnickety of ship-in-a-bottle builders.
    Read More
    Chicago, IL US
    +17737107245
  • Tall Ship Windy
    The massive schooner gently bobs in the Lake Michigan waters as the Chicago skyline towers on the shore. Onboard, hardy sailors relate tales of piracy as they train their passengers to tie knots and unfurl sails. Period lessons abound onboard Windy, the lone vessel helmed by US Coast Guard-certified captains and crews. The nostalgic steed is used to educate visitors on the lake's maritime traditions and explore coastal waters. Windy also plays host to themed adventures that include fireworks shows, pirates explaining city architecture, and pirates complaining about the popularity of pool noodles. Crews strive to make each tour unique, with sailors who expound on their skills as well as performers and educators versed in history, maritime lore, art, and theater.
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    Chicago, IL US
    +13124512700
  • Marine Navigation
    If it's the boater's life for you, you'll want to check out the incredible seaworthy vessels for rent at Marine Navigation in La Grange. Parking is plentiful, so visitors can feel free to bring their vehicles.
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    La Grange, IL US
    +17083520606
  • 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
    +13125271977
  • Millennium Sailing
    What services does your business offer and what makes your business stand out from the competition? Large, comfortable, 40 ft pristine luxury sailing yacht; fully equipped with everything you need for your party including 2 bathrooms, refrigerator, serviceware, grill, pool toys, and play your own music with an iPod connection. Ice and water is also included. What is the experience customers can expect? Amazing views of the city skyline. Experience the quiet motion of the boat under sail and even take the helm if desired. Captain shares knowledge of local city history & architecture. Watch transformation from daylight to city lights on evening cruises. A safe, fun, memorable summer experience! What was the inspiration to start or run this business? After 30 years of sailing experiences while raising my family and entertaining friends on our sailboat, I wanted to share my love of sailing with others. What do you love most about your job? Sailing itself while making a boat move only under the power of the wind and sails, stimulating conversations with clients, Entertaining guests with humor and knowledge with personal stories while sharing information about the skyline and Chicago history and watching clients enjoy themselves!
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    Chicago, IL US
    +16303382785
  • Carefree Boat Club Chicago
    Carefree Boat Club was founded on the principle that adventuring on a boat is always more fun without the chores associated with ownership. Over time, the owners gathered a huge fleet of speedboats, pontoons, and sailboats, launching them into prime boating waters from 27 harbors around the nation. They also assembled a team of maintenance experts to care for the vehicles, removing cleanup and repair responsibilities from club members' agendas. Then, they set their membership rules, keeping a strict ration of ten members to every one vehicle in their fleet to ensure easy boating access. Today, the company maintains a fledgling branch of their operation out of the 31st Street Harbor in Chicago. Their growing fleet already includes a variety of speed boats ready to zip across the smooth surface of Lake Michigan, such as the Sea Ray 240s, 260s, and 270s. In addition to providing unlimited vessel access for members and rentals for non-members, they also arrange a variety of club events at each location. Members go on annual picnics, gather together on holidays, and host seminars for boating-related subjects such as safety, navigation, and how to trick everybody into calling you admiral.
    Read More
    Chicago, IL US
    +18884471540

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