Sailing in Aurora, IL


Private BYOB Sailboat Cruise for Up to Six People from The Salty Dog Sailing Co. (Up to 50% Off)

The Salty Dog Sailing Co.

Burnham Harbor

At Burnham Harbor, board a 34-foot yacht for a nautical adventure on Lake Michigan complete with BYO food and drinks and skyline views

$550 $275

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

Offshore Adventures

Offshore Adventures

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

$220 $69

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

Groups climb aboard a 31-foot sailboat to enjoy a 2-hour cruise during the day, sunset or at night; BYOB friendly

$300 $173

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

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

Come Sailing

Chicago

Captain and full crew take groups of up to six people out onto Lake Michigan, where they can see breathtaking views of the shore and skyline

$350 $105

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

SeaBreeze Charter LLC

SeaBreeze Charter LLC

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

$356 $179

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

$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

75-Minute Sailing Tour for One Adult with Optional Beverage on Tall Ship Windy (38% Off)

Tall Ship Windy

Navy Pier

A 148-foot-long, traditional four-masted schooner sails throughout Lake Michigan for about 75 minutes

$30 $20

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

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

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

30-Minute Kayak Rental for Two or Four at Naperville Kayak (Up to 50% Off)

Naperville Kayak

Naperville Kayak

Float on the waters of downtown Naperville’s Paddleboat Quarry in a kayak

$20 $12

One or Two Full-Day Kayak Rentals with Beginner Land-Based Lessons from Kayak Morris (Up to 52% Off)

Kayak Morris

Morris

On-land lesson covers safety and essential strokes before students pilot craft on a nearby beginner waterway for the rest of the day

$80 $39

Amphibious-Duck Tour of the Wisconsin Dells for Two or Four from Original Wisconsin Ducks (Up to 37% Off)

Original Wisconsin Ducks®

Wisconsin Dells

In an amphibious vehicle, this tour hits Wisconsin Dells sights on land and water, including the Hawk’s Bill rock formation and Dawn Manor

$55.75 $35

Beer Tastings, Flights, and Unfilled Growlers for Two or Four at Metal Monkey Brewing (Up to 33% Off)

Metal Monkey Brewing

Metal Monkey Brewing

Learn about beer and enjoy plenty of samples at the brewery, such as Goodall Day Blonde and Big Chimpin IPA

$21 $14

$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

Amphibious Tour for Two or Four from Dells Army Duck Tour (Up to 38% Off)

Dells Army Duck Tour

Wisconsin Dells

Amphibious, WWII-era vehicles take groups on one-hour trips through the natural landscapes and waterways of the Wisconsin Dells

$60 $39

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

Go City Card

Online Deal

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

$49 $40.50

$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

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

$45 for a Wine-Tasting Package for Two at Waterman Winery and Vineyards, Inc. (Up to $59 Value)

Waterman Winery and Vineyards, Inc.

Clinton

Taste wines made on site, peruse the 12-acre vineyard on a self-guided tour, and take home one bottle of wine

$59 $45

$21 for $35 Worth of Wine and Food at Illinois River Winery

Illinois River Winery

Illinois River Winery

Sample more than 30 handcrafted wines in the tasting room, which serves food

$35 $21

Upper Dells Boat Tour for Two or Four from Dells Boat Tours (Up to 17% Off)

Dells Boat Tours

Upper Dells Boat Tour Dock

Take in all that’s magnificent about the Dells on this two-hour trek through the area’s sandstone formations and secret river passageways

$53.40 $45

Kayaking Class for One, Two, or Four with Naperville Kayak (Up to 51% Off)

Naperville Kayak

Naperville Kayak

Float on the waters of downtown Naperville’s Paddleboat Quarry in a kayak, and learn basic kayaking techniques

$59 $35

$199 for 3.5-Hour Hot Air Balloon Ride Experience from Chicago Balloon Rides Off ($275 Value)

Chicago Balloon Rides

Hampshire

Enjoy scenic countryside views and maybe spot the city skyline during balloon rides from FAA-certified pilots

$275 $199

Wine Tasting for Two, Four, or Six at Downers Grove Wine Shop (Up to 53% Off)

Downers Grove Wine Shop

Downers Grove

Samples of six wines accompany light appetizers during tasting sessions for two, four, or six

$20 $10

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

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

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

Select Local Merchants

Groupon Guide

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