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      Up to 55% Off Chicago Architecture Walking Tour

      Inside Chicago Walking Tours

      A former teacher and improv comedian offers a slice of Chicago architecture during engaging walking tour

      $20 $10

      Up to 60% Off Chocolate Tour of Chicago

      Great Food Tours

      Chicago (0.7 miles)

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

      $50 $25

      57% Off Chicago Prohibition Tour from Chicago Pizza Tours

      Chicago Pizza Tours

      A bus shuttles you to Chicago's former speakeasies while a guide regales the group with tales of Prohibition-era Chicago

      $90 $39

      Up to 67% Off BYOB Cruises from Carefree Boat Club

      Carefree Boat Club

      South of McCormick Place (3.2 miles)

      Sail out from 31st Street Harbor to watch the sunset or admire fireworks

      $175 $69

      Up to 55% Off Running Tours

      Chicago Running Tours & More

      Central Chicago (0.3 miles)

      Professional guides lead sightseeing tours at a jogging pace during excursions that emphasize fun and learning over speed

      $32 $15

      Up to 60% Off the Great Food Tour of Chicago

      Great Food Tours

      Chicago (0.8 miles)

      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

      Up to 60% Off Cupcake Tour of Chicago

      Great Food Tours

      Chicago (0.8 miles)

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

      $50 $25

      Up to 53% Off from Chicago Crime Tours

      Chicago Crime Tours

      Chicago (1.2 miles)

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

      $79.90 $38

      Up to 52% Off Chicago Sports Tour

      Chicago Sports Tours

      Chicago (1.3 miles)

      Saturday sports tours explore Chicago's rich history of football, baseball, basketball, and hockey

      $42 $21

      Up to 51% Off Walking Tour

      WendyCity

      Multiple Locations (0.4 miles)

      Tour the Mag Mile and learn some of its history during a relaxed walk before the stores open

      $50 $25

      Up to 56% Off Pizza Walking Tour

      Slice of Chicago Pizza Tours

      Near North Side (0.9 miles)

      2-hour, 1.2-mile walking tour hits Pizzeria Uno, Pizzeria Ora, and Giordano's in River North to sample deep-dish pizza and learn its history

      $90 $42

      Up to 60% Off an Italian Food Tour of Chicago

      Great Food Tours

      Chicago (0.8 miles)

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

      $50 $25

      Up to 64% Off Chicago Ghost Walk

      Great Food Tours

      Chicago (0.3 miles)

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

      $35 $17

      Half Off a Private Walking Tour

      Free Tours by Foot

      Walking tours visit Lincoln Park landmarks and blues joints or well-known sites in the Loop such as Millennium Park and Daley Plaza

      $150 $75

      53% Off at Wheel Fun Rentals

      Wheel Fun Rentals

      Foster Beach (6.8 miles)

      Bicycles and kayaks help renters discover the Foster Beach area; snacks include sodas, ice cream, and hot dogs

      $43 $20

      Hand-Roll and Decorate Your Own Truffles with a Chocolatier

      Chocolate Truffle-Making Class

      Chocolat (1.9 miles)

      The owner of Chocolat Uzma Sharif demonstrates how to roll chocolate truffles from scratch, incorporating spices, fruits, and liqueurs

      $49

      Explore the Kinetics of Chicago's Massive Moving Bridges

      One-Hour Bridge Lift Tour

      Near North Side (0.8 miles)

      Walk along the Chicago River with a retired civil engineer who explains the history and architecture of the city's movable bridges

      $15

      For the Love of Beer Event at Blackfinn Ameripub

      Fall Beer-Tasting Event at Blackfinn Ameripub

      Blackfinn Ameripub (0.7 miles)

      3 hours of casual merriment at a sports bar in the heart of River North includes bar bites, samples of 6 fall beers, and $3 pints thereafter

      $21.49 $12

      Half Off Interactive Walking Tours

      Stray Boots

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

      $24 $12

      Up to 70% Off Foodie Walking Tour

      Food Tank

      Explore downtown Chicago’s food scene and local landmarks on a walking tour that starts at Millennium Park and ends at the Field Museum

      $65 $25

      Craft Argentine Pastries from Scratch with an Artisan Baker

      Argentinian Pastry-Making Class

      Lucila's Homemade (6.4 miles)

      Lucila Giagrande reveals the secrets of making authentic “alfajores”—Argentine cookies filled with rich dulce de leche

      $48

      Up to Half Off Haunted Halloween Bicycle Tour

      Bobby's Bike Hike

      Streeterville (1.0 miles)

      Professional actors bring Chicago's most famous ghosts to life as groups bike through a former cemetery and other spooky sites

      $49 $25

      50% Off a Haunted-History Walking Tour

      Spirit Expeditions

      South Loop (6.9 miles)

      A two-hour walking tour covers most haunted areas and allows guests to conduct their own paranormal investigation

      $50 $25

      47% Off Day Trip to Michigan Wine Country

      Michigan Wine-County Day Trip

      Chicago (1.1 miles)

      Visit 4 Michigan wineries and taste up to 20 wines during a 9-hour excursion with a hearty lunch and round-trip transportation included

      $150 $79

      42% Off Booze Cruise from Yacht Party Chicago

      Yacht Party Chicago

      Multiple Locations (0.8 miles)

      Yacht sails down Lake Michigan for a three-hour cruise with drinking and dancing, followed by an after party

      $50 $29

      Handcraft a Custom Flower Fascinator with a Professional Milliner

      BYOB Fashion-Design Class

      Oak Park (8.0 miles)

      Milliner and fashion designer Jean Foley teaches you how to make a lovely fabric flower fascinator—materials included—during BYOB classes

      $50

      40% Off a Tour of The Gold Pyramid

      The Gold Pyramid

      The Gold Pyramid (40.4 miles)

      Built as a private home in 1977, the 17,000 sq. ft. pyramid features statues, a moat, a three-pyramid garage, and Egyptian-style furnishings

      $15 $9

      Create Your Own Kimchi Flavor with an Herbal Alchemist

      Kimchi-Making Class

      Eco Collective (3.3 miles)

      Andrea Mattson treats you to several varieties of kimchi before you make your own with local ingredients

      $30

      Make Letterpress Posters with Vintage Wood Type

      BYOB Letterpress Printing Class

      Private Studio - Floyd A. Davis IV (2.2 miles)

      Designer Elizabeth Isakson teaches the basics of letterpressing before you mix ink and craft 5 unique posters using vintage wood type

      $55

      String Together a Beaded Bracelet in a BYOB Jewelry Class

      BYOB Jewelry-Making Class

      Logan Square (5.4 miles)

      Art teacher Katie Netti helps you craft your own bracelet using colorful findings and beads made of metal, glass, and other materials

      $30

      50% Off a Quincy Street Distillery Tour

      Quincy Street Distillery

      Riverside (10.6 miles)

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

      $44 $22

      Valentino Vineyards & Winery – 60% Off Tasting, Tour & Seminar

      Valentino Vineyards & Winery

      Long Grove (27.7 miles)

      Following a brief tour in the vineyard, guests enter a winery to sample five estate wines during wine appreciation seminar

      $48 $19

      Use Leaves to Print Greeting Cards at a BYOB Workshop

      BYOB Card-Printing Workshop

      Albany Park (7.5 miles)

      Jenny Dey teaches you how to print custom greeting cards with fabric, paper, and local plant leaves during a BYOB workshop

      $40

      Start a Sketchbook Journal Devoted to Your Pet During a BYOB...

      BYOB Pet Sketchbook Class

      Ravenswood (6.6 miles)

      Painter Anne Leuck Feldhaus explains her creative process & helps you create a sketchbook filled with drawings and text about a favorite pet

      $48

      50% Off Tour at Ellwood House Museum

      Ellwood House Museum

      DeKalb (58.2 miles)

      Tours of the estate of Isaac Ellwood, one of the wealthiest men in Illinois in the late 1800s, feature a barbed-wire exhibit and a playhouse

      $16 $8

      Up to 50% Off at Illinois River Winery

      Illinois River Winery

      North Utica (81.0 miles)

      Sample more than 30 handcrafted wines from the tasting room or sip wines while touring the facility

      $30 $17

      Up to 55% Off Bahamas Cruise for Two

      Celebration Cruise Line

      West Palm Beach to Bahamas (1129.9 miles)

      Caribbean ocean liner cruises from West Palm Beach toward Bahamas; spa, pool, Las Vegas–style casino, and free meals on board

      $398 $179

      ✈ 8-Day Kenya Safari with Airfare

      Safari in Kenya with Airfare

      Intercontinental Hotel Nairobi (7953.3 miles)

      Visit an elephant nursery, ride a boat through Lake Naivasha, and take game drives through Masai Mara reserve on this 8-day Kenya safari

      $2,299