Sailing in Old Irving Park, Chicago


Semi-Private Sunset Cruise for Two or Basic Intro to Sailing Course at Chicago Yacht Share (52% Off)

Chicago Yacht Share
Lakeview/Lincoln Park

Instructor teaches basic sailing techniques to complete novices on Lake Michigan; couples enjoy a romantic sunset cruise

$400 $190

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

Offshore Adventures
Chicago

$199 for private two-hour BYOB sailing cruise for six ($660 value).

$220 $69

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Two-Hour Sailing Charter for Up to Six from Come Sailing (Up to 70% Off). Three Options Available.

Come Sailing
Chicago

$175 for a two-hour sailing charter for up to six people, valid weekdays after 10 a.

$350 $105

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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

$399 for a three-hour private BYOB sailing charter for up to six ($750 value).

$250 $99

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Two-Hour Sailing Charter for Up to Six from SeaBreeze Charter (50% Off). Two Options.

SeaBreeze Charter LLC
Chicago

American Sailing Association–certified captain entertains passengers during two-hour charters on Lake Michigan; BYOB and food

$356 $179

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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

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$499 for Three-Hour BYOB Sailing Cruise for Up to Six on Luxury Yacht from Windy City Sailing ($600 Value)

Windy City Sailing
Lakeview

Take in one-of-a-kind views of Chicago on this three-hour BYOB cruise aboard a luxury sailing yacht

$600 $499

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Two-Hour Private Cruise for Up to 6 from New Buffalo Sailing Excursions (Up to 44%Off). Four Options Available.

New Buffalo Sailing Excursions
New Buffalo

Here are some things to know about the sailing excursions.

$300 $173

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Maze Visit and Games for Two, Four, or Eight at Amazing Chicago's Funhouse Maze on Navy Pier (Up to 62% Off)

Amazing Chicago's Funhouse Maze on Navy Pier
Amazing Chicago's Funhouse Maze at Navy Pier

A spinning tunnel and the corridor of confusion lay inside a 4,000-square-foot, Chicago-history-themed maze on Navy Pier

$25.98 $14

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Tickets to the Pub Night Sail on Tall Ship Windy (Up to 55% Off)

Tall Ship Windy of Chicago
Navy Pier

A 148-foot-long, traditional four-masted schooner sails throughout Lake Michigan

$50 $25

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

3rd Coast Cruising
DuSable Harbor

$99 for one three-hour introductory sailing or racing lesson ($300 value).

$300 $99

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Chicago Explorer Pass Including Admission to Three or Five Attractions from 20+ Options. Pay Nothing at Gate.

Go City Card
Burnham Harbor

Card grants free admission to 3 or 5 Chicago museums, tours, and attractions, chosen from over 20 options

$49 $40.50

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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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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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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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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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Sunset Nature Kayak Tour for One or Two from Chicago River Paddle & Kayak (40% Off)

Chicago River Paddle & Kayak
Roscoe Village

Guests float down the Chicago River in kayaks or canoes, spying native wildlife such as waterfowl and turtles

$50 $30

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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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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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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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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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Monday Night Sunset Cocktail Cruise Aboard the Anita Dee II Yacht

Anita Dee II Yacht
Chicago

$25 $16.50

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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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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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Downtown Naperville Food Tour for One or Two from Naperville Bites and Sites (Up to 22% Off)

Naperville Bites and Sites
Chicago

Eat, walk, and discover Naperville’s historic neighborhood during a culinary and cultural food tour

$48 $40

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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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$20 for $40 worth of Drinks at O 'Donnell's pub (Up to 40% Off)

O 'Donnell's pub
Mayfair

Enjoy cold beers and cocktails and friendly conversation at this neighborhood corner pub

$20 $12

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Interactive Walking Tours of Chicago from Stray Boots (50% Off). Four Options Available.

Stray Boots
Burnham Harbor

Clues, trivia, and riddles lead explorers through vibrant neighborhoods via the Stray Boots iPhone or Android app

$24 $12

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$49 for a Six-Bottle In-Home Wine Tasting for Up to 12 from PRP Wine International ($200 Value)

PRP Wine International
Chicago

Wine enthusiasts sample up to six global wines in-home as a staffer expounds on the winemaking process and shares food-pairing ideas

$200 $49

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$55 for a Two-Hour Wine Tasting for 12 to 16 People from Wines for Humanity ($250 Value)

Wines for Humanity
Burnham Harbor

Professional wine advisor teaches guests to discern distinctive notes in six exclusive vintages and pair them with appropriate dishes

$250 $55

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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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Lake Paddle

Kayak Chicago - North Avenue Beach
North Side

$75.21 $45.11

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Sidewalk Food Tours of Chicago: Wicker Park

Wicker Park
Bucktown

$55 $43.75

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Little Arabia Culture and Food Tour for One or Two from Spice of Life Tours (Up to 51% Off)

Spice of Life Tours
Chicago

Tour introduces participants to the food and culture of Little Arabia in Albany Park, and includes tastings and a henna tattoo

$140 $69

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3.5-Hour Food and Culture Tour for One or Two from Spice of Life Tours (Up to 54% Off)

Spice of Life Tours
India Book House

Tour introduces participants to the food and culture of Devon Avenue, and includes tastings and a stop by a henna tattoo parlor

$170 $79

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Wednesday Night Sunset & Fireworks Cruise

Anita Dee II Yacht at DuSable Harbor
Chicago

$31 $17.25

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$62 for a 90-Minute Architectural Boat Tour for Two from Chicago Line Cruises ($84 Value)

Chicago Line Cruises
Chicago

Award-winning Docents tell the stories behind over 50 “cloud busters” and narrate historical events that influenced the present-day skyline

$84 $62

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Chicago Helicopter Tour for Two in the Daytime or Nighttime from Chicago Helicopter Experience

Chicago Helicopter Experience
Bridgeport

Passengers soar over the skyline, marveling at the Willis Tower, John Hancock Building, and Trump Tower

$296 $275

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Sightseeing Tour or Brunch Tour for One or Two from Chicago's Finest Tours (Up to 52% Off)

Chicago's Finest River Walk Tour
Wrigley Building Plaza

Tours take guests along Chicago’s historic River Walk, around the Loop, or to a hearty brunch buffet

$50 $24

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Pepsi Tall Ships Chicago Festival 2016 on July 28 - 31 (Up to 23% Off)

Pepsi Tall Ships Chicago 2016
Navy Pier

Navy Pier fills up with 14 tall ships such as two-masted schooners and a Viking longboat during this four day festival

$70 $55

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Tour by Bus for Two or Four from Chicago Crime Tours (Up to 38% 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

$159.80 $99

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$75 for a Lazy River Tubing Outing with Round-Trip Transport from Cannonball Productions ($93.65 Value)

Cannonball Productions
Bus Pick-Up

Enjoy a day of river floating and an afternoon at the park, basketball, slip n’ slide, volleyball, and an all-you-can-eat taco bar

$93.65 $75

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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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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

$60 $28

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River North Wine Fest - Saturday September 17, 2016 / Noon to 4:00pm

Moe's Cantina and Old Crow Smokehouse River North
Near North Side

$50 $29

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Walking Food Tour for One or Two from Sidewalk Food Tours of Chicago (Up to 37% Off)

Sidewalk Food Tours of Chicago
Wicker Park

Enjoy a roving lunch of five different tastings while learning about the history and culture of either River North or Wicker Park

$55 $35

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Gangster History Tour from The Barrel Run (Up to 40% Off)

The Barrel Run
Near North Side

A bus styled to look like an actual beer barrel sets a party-friendly tone for these educational tours of Chicago’s gangster-filled history

$70 $49

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Sunset Paddle - Sunday August 28, 2016 / 7:00pm

Kayak Chicago - Chicago River
Goose Island

$64.31 $38.91

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One, Two, or Four Tickets to the Chicago Gangster Tour from Second City Tours (Up to 61% Off)

Second City Tours
Holy Name Cathedral

Guides recount local legends about Al Capone, Dillenger, and more during a 90-minute gangster tour

$30 $14

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Select Local Merchants

  • Pat Hays
    When you need something to do on your day off, visit Pat Hays in Chicago and indulge in a day filled with fun and adventure. For a different kind of sport, strike up a game of paintball at Pat Hays. Join hot yoga enthusiasts at Pat Hays and open up your mind, body (and pores) to a healthier lifestyle. Stretch your body to the max at aerial yoga classes. Parking is plentiful, so guests can feel free to bring their vehicles. So as you can see, Pat Hays is the place to be this weekend.
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    4637 North Milwaukee Ave
    Chicago, IL US

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