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      Up to 51% Off a Helicopter Tour of Chicago

      Chicago Helicopter Express


      Helicopters cruise 800 feet above the Chicago skyline past such famed sights as Willis Tower, Wrigley Field, and Navy Pier

      $360 $199

      Up to 60% Off Chocolate Tour of Chicago

      Great Food Tours


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

      $50 $25

      Up to 51% Off an After-Work Cruise


      Cruises aboard a yacht with dance floors and bars provide brilliant evening views of the Chicago skyline

      $25 $13

      Up to 60% Off Cupcake Tour of Chicago

      Great Food Tours


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

      $50 $25

      Discover the Kinetic Art of Chicago's Moving Bridges

      Moving-Bridge Walking Tour


      Walk the streets of the Loop with civil engineer Jim Phillips and watch the Chicago River's movable bridges in action


      50% Off Segway Tours for Two

      Bike and Roll Chicago

      Multiple Locations

      Segways effortlessly glide through the city streets, allowing riders to breeze by Frank Lloyd Wright's Robie House or Soldier Field

      $138 $69

      Up to 38% Off from Weird Chicago Tours

      Weird Chicago Tours

      Near North Side

      Travel by bus to the former crime scenes, red-light districts, gangster hangouts, or ghost-sighting spots of Chicago's storied past

      $60 $39

      Up to Half Off Chicago History Tour in the Pedway

      Chicago's Finest Tours

      The Loop

      The Pedway's network of heated tunnels and sky bridges ferries guests between landmarks; choose one of three 2.5-hour tours

      $50 $25

      Up to 51% Off Walking Ghost Tour for Two or Four

      Haunted Hometowns

      Multiple Locations

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

      $40 $20

      Up to 53% Off from Chicago Crime Tours

      Chicago Crime Tours


      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

      37% Off Sunset Tour for Two from Chicago Helicopter Express

      Chicago Helicopter Express


      Climate-controlled helicopters with leather seats and noise-canceling headsets take twosomes 800-1200 feet up for a unique view of Chicago

      $429 $269

      41% Off a Stunt-Airplane or Warplane Ride

      Gauntlet Warbirds

      Sugar Grove

      A seasoned flight instructor leads a 40-minute joy ride aboard an Extra 300L aerobatic plane or a T-6 Texan warplane

      $440 $259

      Up to 60% Off the Great Food Tour of Chicago

      Great Food Tours


      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 Half Off Urban Dare Adventure Race for Two

      Urban Dare

      Allstars Sports Bar

      Fast-paced competition challenges teams of two with trivia, photo hunts, and mental and physical challenges

      $90 $45

      Up to 50% Off Absolutely Chicago Segway Tours

      Absolutely Chicago Segway Tours


      Ride up to some of Chicago's most iconic landmarks as the sun sets and the skyline begins to glow

      $50 $30

      Up to 44% Off Loop Interior Architecture Tour for Two

      Chicago Detours

      The Loop

      Featured in the Chicago Reader, guides lead groups through architecturally striking interiors and share photos and videos via iPads

      $52 $29

      Up to 50% Off Fine Wine

      Glunz Family Winery & Cellars


      Variety of wine made in small batches, including table wine, seasonal wine, and fortified wine

      $20 $11

      Up to 78% Off from TikiBoat Chicago

      TikiBoat Chicago

      Monroe Harbor

      36-foot party barge with water slide ferries guests onto Lake Michigan and Chicago River; amenities include stereo, grill, and full bathroom

      $1799 $399

      Up to 56% Off Pizza Walking Tour

      Slice of Chicago Pizza Tours

      Near North Side

      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

      50% Pub Crawl or Brunch Tour

      Chicago's Finest Tours

      The Loop

      Groups roam the pedway's watering holes while hearing about prohibition days, or combine history with brunch

      $80 $40

      Chicago Architecture Foundation – $13 for a "Must-See Chicago"...

      Chicago Architecture Foundation


      Stroll past such Chicago icons as the Art Institute, Willis (Sears) Tower, Wrigley Building, Chicago Theatre, and John Hancock Center

      $20 $13

      Up to 57% Off Social Game Experience

      Waxwing Puzzle Co.

      Logan Square

      Players take part in a role-playing event that is set in the prohibition era and pulls from mob folklore

      $40 $20

      54% Off Scavenger Dash

      Sierra Adventure Sports

      Near North Side

      Teams of two traverse the streets of Chicago as they find clues, collect items, take pictures, and complete challenges

      $127.59 $59

      Up to 55% Off Chicago Architecture Walking Tour

      Inside Chicago Walking Tours

      On Location

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

      $20 $10

      50% Off a Haunted-History Walking Tour

      Spirit Expeditions

      South Loop

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

      $50 $25

      Up to 61% Off Urban Scavenger Hunt

      CityScape Adventures

      Cubby Bear

      Five-hour scavenger hunt takes participants through 12 challenges that encourage them to explore the city while testing their mettle

      $100 $40

      Up to 57% Off Urban Scavenger Race

      Race & Seek

      Dick's Last Resort

      Teams navigate the city in search of 14 clues, which they must document via smart phone; first prize is $500 and entry for the championship

      $80 $39

      Half Off a Private Walking Tour

      Free Tours by Foot

      On Location

      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

      Up to 50% Off an Inside Chicago Grand Tour

      American Sightseeing Chicago

      The Loop

      A bus ferries visitors to the North and South Sides, showing them major parks, the Museum Campus, and the sights along Lake Shore Drive

      $45 $25

      50% Off Flight Lesson

      South Chicago Flying Lessons

      South Chicago Flying Lessons

      Give the gift of flight as an FAA-certified instructor guides 30-minute flight where the students can fly the plane for up to 15 minutes

      $199.99 $99

      2014 Haunted America Conference – Up to 51% Off Tickets

      2014 Haunted America Conference

      Lincoln Theater

      Watch experts such as Troy Taylor, April Slaughter, and Rick Redfern talk on subjects such as ghost hunting and cryptozoology

      $50 $25

      51% off Cemetery Ghost Hunt from Haunted Hometowns

      Haunted Hometowns, Corp.


      Ghost-seekers walk through moon-lit cemeteries in the dead of night during tour as guides relate tales of local specters

      $90 $45

      Forage for Wild Edibles with a Foodie Farmer

      Scenic Foraging Excursion


      Farmer April Morris teaches you to find morels, garlic mustard, and raspberry shoots in the wild—and how to use them in the kitchen


      Half Off Interactive Walking Tours

      Stray Boots

      Online Deal

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

      $24 $12