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Sailing in Des Plaines, IL


Offshore Adventures: Two-Hour BYOB Sailing Cruise for Two or Six from Offshore Adventures Chicago (Up to 70% Off)

Two-Hour BYOB Sailing Cruise for Two or Six from Offshore Adventures Chicago (Up to 70% Off)

Offshore Adventures

Chicago

Daytime or sunset Lake Michigan cruises delight with views of the Chicago skyline; passengers can bring their own drinks and playlists

$220 $69

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

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

3rd Coast Cruising

DuSable Harbor

US Coast Guard–certified captains and certified instructors welcome sailors aboard 30-foot or larger boat

$300 $99

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360 CHICAGO, Formerly John Hancock Observatory: Sun and Stars Admission for One, Two, or Four Adults at 360 CHICAGO (25% Off)

Sun and Stars Admission for One, Two, or Four Adults at 360 CHICAGO (25% Off)

360 CHICAGO, Formerly John Hancock Observatory

Chicago

94 floors up, take in stunning panoramas of Chicago and its sky-high architecture bordered by sparkling Lake Michigan

$24 $18

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Church Street Brewing Company: $26 for a Brew Package for 2 with Pints, Glasses, & Growler at Church Street Brewing Company ($41 Value)

$26 for a Brew Package for 2 with Pints, Glasses, & Growler at Church Street Brewing Company ($41 Value)

Church Street Brewing Company

Itasca

Traditional German brewing practices produce such star beers as the sweet, malty Heavenly helles and the nutty dark-amber Bob’s Your Dunkel

$41 $26

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Bike and Roll Chicago: Sunset Segway Tour from Millennium Park for One or Two from Bike and Roll Chicago (Up to 50% Off)

Sunset Segway Tour from Millennium Park for One or Two from Bike and Roll Chicago (Up to 50% Off)

Bike and Roll Chicago

Millenium Park

Easily maneuverable segway vehicles traverse the lakefront for views of the Chicago skyline, parks, and lakeside museums

$75 $39

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Chicago Hauntings Ghost Tour: Choice of Ghost Bus Tour for One or Two at Chicago Hauntings Ghost Tour (19% Off)

Choice of Ghost Bus Tour for One or Two at Chicago Hauntings Ghost Tour (19% Off)

Chicago Hauntings Ghost Tour

Chicago Hauntings Ghost

Paranormal experts narrate a bus tour; specialty tours explore haunted sites inspired by the city’s gothic past or the notorious H.H. Holmes

$36 $29

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Wateriders Kayak Tours: Architecture and History Kayak Tour or Shady Chicago Kayak Tour for Two or Four from Wateriders (Up to 52% Off)

Architecture and History Kayak Tour or Shady Chicago Kayak Tour for Two or Four from Wateriders (Up to 52% Off)

Wateriders Kayak Tours

Riverwalk

Guides spin true tales of Windy City history and architecture; the gritty underbelly takes center stage in the Ghosts and Gangsters tour

$130 $65

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Second City Tours: Chicago Food Crawl for One, Two, or Four from Second City Tours (Up to 60% Off)

Chicago Food Crawl for One, Two, or Four from Second City Tours (Up to 60% Off)

Second City Tours

Near North Side

Head to River North for deep-dish pizza, Chicago-style hot dogs, Mike Ditka’s favorite italian-beef sandwiches, and dessert

$50 $23

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Quincy Street Distillery: $20 for a Distillery Tour for Two with Two Glencairn Glasses at Quincy Street Distillery ($44 Value)

$20 for a Distillery Tour for Two with Two Glencairn Glasses at Quincy Street Distillery ($44 Value)

Quincy Street Distillery

Riverside

60- to 90-minute tour of a distillery that produces 12 artisanal, small-batch spirits; each guest brings home a Glencairn glass

$44 $20

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Second City Tours: Pizza Parade Tour for One, Two, or Four from Second City Tours (Up to 60% Off)

Pizza Parade Tour for One, Two, or Four from Second City Tours (Up to 60% Off)

Second City Tours

Chicago

Guides will lead you through River North to sample pizza from local eateries, including the original Uno Pizzeria & Grill

$50 $23

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Chicago Crime Tours: Tour by Bus for Two or Four from Chicago Crime Tours (Up to 44% Off)

Tour by Bus for Two or Four from Chicago Crime Tours (Up to 44% Off)

Chicago Crime Tours

Near North Side

Learn about more than 100 years of Chicago’s crime history in a 90-minute tour of famous crime scenes and landmarks

$79.90 $49

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Second City Tours: Winter Whiskey Crawl for One, Two, or Four from Second City Tours (Up to 59% Off)

Winter Whiskey Crawl for One, Two, or Four from Second City Tours (Up to 59% Off)

Second City Tours

Near North Side

Explore River North hotspots and sip blended and malt whiskeys paired with breads, cheeses, and meats

$100 $49

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Second City Tours: Cupcake Crawl for One, Two, or Four from Second City Tours (Up to 60% Off)

Cupcake Crawl for One, Two, or Four from Second City Tours (Up to 60% Off)

Second City Tours

Water Tower Place

The city’s favorite cupcake hot spots are visited during this tour: Sprinkles, Sacred Grounds, More, and Crumbs

$50 $23

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Second City Tours: Chocolate Crawl for One, Two, or Four from Second City Tours (Up to 60% Off)

Chocolate Crawl for One, Two, or Four from Second City Tours (Up to 60% Off)

Second City Tours

Water Tower Place

Get your chocolate fix during this tour that visits five of the city’s most beloved sweet-treat havens

$50 $23

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Second City Tours: One, Two, or Four Tickets to the Beer & Bacon Binge Food Tour from Second City Tours (Up to 59% Off)

One, Two, or Four Tickets to the Beer & Bacon Binge Food Tour from Second City Tours (Up to 59% Off)

Second City Tours

Near North Side

Explore three River North hotspots and sip craft beer paired with bacon snacks

$100 $49

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Second City Tours: Underground Pedway Tour for One, Two, or Four from Second City Tours (Up to 61% Off)

Underground Pedway Tour for One, Two, or Four from Second City Tours (Up to 61% Off)

Second City Tours

The Loop

90-minute walking tour takes guests through the underground walkways that connect a number of Chicago buildings

$30 $14

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Second City Tours: One, Two, or Four Tickets to the Wine and Cheese Walk from Second City Tours (Up to 59% Off

One, Two, or Four Tickets to the Wine and Cheese Walk from Second City Tours (Up to 59% Off

Second City Tours

Near North Side

Travel to three upscale restaurants and bars and sip nine or more samples of wine paired with assorted cheeses and small bites

$100 $49

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Best Tours: Wine and Cheese Tour of Chicago with 12 Tastings and Pairings from Best Tours (Up to 58% Off)

Wine and Cheese Tour of Chicago with 12 Tastings and Pairings from Best Tours (Up to 58% Off)

Best Tours

Chicago

Stroll along the Magnificent Mile and through the Gold Coast as you sample 12 bites of cheese paired with sips of wine

$100 $49

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Penrose Brewing Company: $15 for a Brewery Tour for Two or Four with Beer at Penrose Brewing Company ($20 Value)

$15 for a Brewery Tour for Two or Four with Beer at Penrose Brewing Company ($20 Value)

Penrose Brewing Company

Geneva

Learn about the Geneva brewery’s craft-beer brewing process and sip two 12 oz. beers

$40 $29

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Best Tours: Drunk History of Chicago Tour at Four Pubs for One, Two, or Four from Best Tours (Up to 60% Off)

Drunk History of Chicago Tour at Four Pubs for One, Two, or Four from Best Tours (Up to 60% Off)

Best Tours

Chicago

Visit four local pubs to sample alcoholic beverages and shots, learn about the history of the city, and pick up some fake history too

$50 $25

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Best Tours: Cupcake Tour of Chicago with Six Tastings for One, Two, or Four from Best Tours (Up to 68% Off)

Cupcake Tour of Chicago with Six Tastings for One, Two, or Four from Best Tours (Up to 68% Off)

Best Tours

Chicago

Tours make six stops along Michigan Avenue, visiting a century-old shop, one with 50 varieties of cupcake, and another with gelato

$50 $19

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Argus Brewery: 90-Minute Brewery Tour for Two, Four, or Six with Tastings, Snacks, and Glasses at Argus Brewery (Up to 57% Off)

90-Minute Brewery Tour for Two, Four, or Six with Tastings, Snacks, and Glasses at Argus Brewery (Up to 57% Off)

Argus Brewery

Roseland

During a 90-minute tour, guests learn about the historic origins of the brewery and the neighborhood while sampling craft brews

$30 $15

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Frank Lloyd Wright Home and Studio: Tour the Frank Lloyd Wright Home and Studio at Frank Lloyd Wright Home and Studio

Tour the Frank Lloyd Wright Home and Studio at Frank Lloyd Wright Home and Studio

Frank Lloyd Wright Home and Studio

Oak Park

$17 $9.50

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Second City Tours: Coffee & Hot Cocoa Crawl for One, Two, or Four from Second City Tours (Up to 60% Off)

Coffee & Hot Cocoa Crawl for One, Two, or Four from Second City Tours (Up to 60% Off)

Second City Tours

Chicago

Tour-goers sample coffees, cocoa, desserts, and pastries at some of River North’s most delicious spots

$50 $23

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Best Tours: Chicago Ghost Walk for One, Two, or Four from Best Tours (Up to 65% Off)

Chicago Ghost Walk for One, Two, or Four from Best Tours (Up to 65% Off)

Best Tours

Chicago

Tours visit haunted spots in search of apparitions, including the sites of the Iroquois Theatre fire and the Eastland shipwreck

$35 $17

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Best Tours (Chicago): Admission for One, Two, or Four to the Chicago Riverwalk Food Tour from Best Tours (Up to 60% Off)

Admission for One, Two, or Four to the Chicago Riverwalk Food Tour from Best Tours (Up to 60% Off)

Best Tours (Chicago)

Chicago

Tours make stops at eateries located along the Chicago Riverwalk and introduce tour-goers to Chicago’s history and famous architecture

$50 $25

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Best Tours (Chicago): Gangster Tour of Chicago for One, Two, or Four from Best Tours (Up to 65% Off)

Gangster Tour of Chicago for One, Two, or Four from Best Tours (Up to 65% Off)

Best Tours (Chicago)

Chicago

Tour-goers take a 90-minute jaunt past iconic landmarks and mob movie filming locations while learning about Chicago’s gangster past

$35 $17

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Cannonball Productions: $79 for a Southwest Michigan Winery Day Tour for One from Cannonball Productions ($150 Value)

$79 for a Southwest Michigan Winery Day Tour for One from Cannonball Productions ($150 Value)

Cannonball Productions

 

Sample wines from Southwest Michigan wineries including Lemon Creek, St. Julian, and Round Barn on this day tour; includes lunch

$150 $79

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Best Tours: Great Food Tour of Chicago with Six Tastings for One, Two, or Four from Best Tours (Up to 60% Off)

Great Food Tour of Chicago with Six Tastings for One, Two, or Four from Best Tours (Up to 60% Off)

Best Tours

Chicago

Tours make six stops along Michigan Avenue, visiting the originator of deep-dish pizza and an eatery serving up Chicago-style hot dogs

$50 $25

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Fox River Distilling Company: Tour for Two or Four with Bloody-Mary Mix, Hats, and Rocks Glasses at Fox River Distilling Company (Up to 43% Off)

Tour for Two or Four with Bloody-Mary Mix, Hats, and Rocks Glasses at Fox River Distilling Company (Up to 43% Off)

Fox River Distilling Company

Geneva

Tour the distillery, which produces vodka, gin, and moonshine, and leave with bloody-mary mixes, hats, and rocks glasses

$47 $27

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Haunted Hometowns, Corp.: Three-Hour Elgin Cemetery Ghost Hunt for One, Two, or Four from Haunted Hometowns (55% Off)

Three-Hour Elgin Cemetery Ghost Hunt for One, Two, or Four from Haunted Hometowns (55% Off)

Haunted Hometowns, Corp.

Bluff City Cemetery

Ghost-seekers walk through moon-lit a cemetery in the dead of night holding EMF meters during tour as guides relate tales of local specters

$70 $35

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Lake Katherine Nature Ctr/Botanic Garden: Two-Hour Kayaking for One or Two from Lake Katherine Nature Ctr/Botanic Garden (Up to 31% Off)

Two-Hour Kayaking for One or Two from Lake Katherine Nature Ctr/Botanic Garden (Up to 31% Off)

Lake Katherine Nature Ctr/Botanic Garden

Palos Heights

Guests rent kayaks for paddling past beavers, herons, and turtles of Lake Katherine, with walks through scenic botanical gardens afterwards

$16 $12

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Best Tours: Chocolate Tour of Chicago with Seven Tastings for One, Two, or Four from Best Tours (Up to 60% Off)

Chocolate Tour of Chicago with Seven Tastings for One, Two, or Four from Best Tours (Up to 60% Off)

Best Tours

Chicago

Sample Aztec chocolate drinks, cupcakes, truffles, and chocolate donuts during two-hour chocolate tour along the Magnificent Mile

$50 $25

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Best Tours (Chicago): Admission for One, Two, or Four to the Beer & Bacon Tour of Chicago from Best Tours (Up to 58% Off)

Admission for One, Two, or Four to the Beer & Bacon Tour of Chicago from Best Tours (Up to 58% Off)

Best Tours (Chicago)

Chicago

Visit local eateries to try five seasonal beer and bacon samples

$100 $49

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Best Tours (Chicago): Admission for One, Two, or Four to the Chinatown Food Tour of Chicago from Best Tours (Up to 60% Off)

Admission for One, Two, or Four to the Chinatown Food Tour of Chicago from Best Tours (Up to 60% Off)

Best Tours (Chicago)

Chicago

Tours of Chicago’s Chinatown make stops for dumplings, tea, and fortune and almond cookies

$50 $25

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Acquaviva Winery -: Winery Tour for Two or Four Plus Bottles to Take Home at Acquaviva Winery (Up to 41% Off)

Winery Tour for Two or Four Plus Bottles to Take Home at Acquaviva Winery (Up to 41% Off)

Acquaviva Winery -

Maple Park

Tour a picturesque winery with striking architecture before enjoying a glass of wine in the tasting room and selecting a bottle to take home

$64 $39

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Second City Tours: One, Two, or Four Tickets to Belmont Food Binge Tour from Second City Tours (Up to 60% Off

One, Two, or Four Tickets to Belmont Food Binge Tour from Second City Tours (Up to 60% Off

Second City Tours

Lakeview

Enjoy Lakeview’s ethnic- and American-food offerings, including tacos, French pastries, falafel, and grilled cheese

$50 $23

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Second City Tours: Ghost Tour for One, Two, or Four from Second City Tours (Up to 61% Off)

Ghost Tour for One, Two, or Four from Second City Tours (Up to 61% Off)

Second City Tours

John Hancock Center

90-minute tour explores the tragic side of Chicago history with stops to locales said to be marked by paranormal activity

$30 $14

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Robie House: Frederick C. Robie House Tour at Robie House

Frederick C. Robie House Tour at Robie House

Robie House

Hyde Park

$17 $9.50

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Big Bus Tours-Chicago: 24- or 48-Hour Kid or Adult Ticket for a Hop On, Hop Off Chicago Bus Tour from Big Bus Tours

24- or 48-Hour Kid or Adult Ticket for a Hop On, Hop Off Chicago Bus Tour from Big Bus Tours

Big Bus Tours-Chicago

Chicago

Narrated double-decker bus tour of Chicago sights; hop on and off at your leisure, with discounts and free treats at local businesses

$39

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Brews Cruise Chicago: Brewery Tour in Southwest Chicagoland from Brews Cruise Chicago (Up to  Off). Two Options Available.

Brewery Tour in Southwest Chicagoland from Brews Cruise Chicago (Up to Off). Two Options Available.

Brews Cruise Chicago

Chicago

A half-day tour takes you to working breweries where you’ll sample beverages and learn what makes some of your favorite beers so good

$130 $65

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Best Tours (Chicago): Pizza Tour of Chicago for One, Two, or Four from Best Tours (Up to 60% Off)

Pizza Tour of Chicago for One, Two, or Four from Best Tours (Up to 60% Off)

Best Tours (Chicago)

Chicago

Guest stroll past famous Chicago landmarks on their way to the city’s best pizza joints for samples, demos, and history lessons

$50 $22

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Mike's E-Bikes: Starved Rock Electric Bike Tour for Two, Three, or Four from Mike's E-Bikes (Up to 49% Off)

Starved Rock Electric Bike Tour for Two, Three, or Four from Mike's E-Bikes (Up to 49% Off)

Mike's E-Bikes

Starved Rock

See Starved Rock’s pictureqsue landscapes and canyons on a fun and scenic bike tour

$135 $89

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Best Tours: Italian Food Tour of Chicago with Five Tastings for One, Two, or Four from Best Tours (Up to 60% Off)

Italian Food Tour of Chicago with Five Tastings for One, Two, or Four from Best Tours (Up to 60% Off)

Best Tours

Chicago

Sample Chicago-style pizza, italian beef, and artisan products during a two-hour Italian-food tour along the Magnificent Mile

$50 $25

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Second City Tours: One, Two, or Four Tickets to the Burger & Beer Binge Food Tour from Second City Tours (Up to 59% Off)

One, Two, or Four Tickets to the Burger & Beer Binge Food Tour from Second City Tours (Up to 59% Off)

Second City Tours

Near North Side

Explore three River North hotspots and sip craft beers paired with specialty burgers

$100 $49

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Haunted Hometowns, Corp.: Two-Hour Walking Ghost Tour of Aurora or Naperville for One, Two, or Four from Haunted Hometowns (Up to 56% Off)

Two-Hour Walking Ghost Tour of Aurora or Naperville for One, Two, or Four from Haunted Hometowns (Up to 56% Off)

Haunted Hometowns, Corp.

Multiple Locations

Ghost-seekers clutch EMF meters on lantern-lit tours through historic and haunted sites as guides relate tales of local specters

$20 $12

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Slice of Chicago Pizza Tours: Chicago Pizza Walking Tour for Two or Four from Slice of Chicago Pizza Tours (Up to 44% Off)

Chicago Pizza Walking Tour for Two or Four from Slice of Chicago Pizza Tours (Up to 44% Off)

Slice of Chicago Pizza Tours

Near North Side

2-hour, 1.2-mile walking tour hits several pizzerias like Pizzeria Uno and Giordano’s in River North to sample pizza and learn its history

$100 $60

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Second City Tours: Loop Architecture Tour for One, Two, or Four from Second City Tours (Up to 61% Off)

Loop Architecture Tour for One, Two, or Four from Second City Tours (Up to 61% Off)

Second City Tours

The Loop

90-minute walking tour takes guests to view some of the city’s most remarkable buildings

$30 $14

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Gray Line Chicago: 4-Hour Grand Tour with Pizza or Hancock Observation-Deck Visit for One from Gray Line Chicago (Up to 29% Off)

4-Hour Grand Tour with Pizza or Hancock Observation-Deck Visit for One from Gray Line Chicago (Up to 29% Off)

Gray Line Chicago

Palmer House Hilton - Gift Shop

A bus takes sightseers to the best Chicago locales, then treats them to a pizza or a trip up to the Hancock Center’s observation deck

$39 $29

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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.
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    400 East Monroe Street
    Chicago, IL US
  • 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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    600 E Grand Ave.
    Chicago, IL US
  • Denna Lawn & Marine
    Get your sea legs ready! Denna Lawn and Marine in Bensenville provides quality vessels so you can have a boating experience that is both relaxing and fun. Parking is plentiful, so patrons can feel free to bring their vehicles.
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    560 North York Road
    Bensenville, IL US
  • Wilmette Park District
    Nature lovers will appreciate Wilmette's Wilmette Park District. From front kicks to roundhouses, these kickboxing classes will teach you the fundamentals. Parking is plentiful, so guests can feel free to bring their vehicles.
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    200 Lake Avenue
    Wilmette, IL US
  • Laserperformance Hedlund Marine Sports
    Take a nautical adventure around Evanston when you rent a vessel from Laserperformance Hedlund Marine Sports. Parking is plentiful, so visitors can feel free to bring their vehicles.
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    2112 Jackson Avenue
    Evanston, IL US
  • Boater's World Discount Marine Center
    Cast away all your troubles and take a relaxing boating trip with Boater's World Discount Marine Center in Schaumburg. Parking is plentiful, so patrons can feel free to bring their vehicles.
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    697 East Golf Road
    Schaumburg, IL US

Groupon Guide

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