Tours in Griffith

$50 for an Architectural Boat Tour for Two ($84 Value). Reservation through Groupon Required.

Chicago Line Cruises

Chicago

Docent-narrated tours cover the history of Chicago’s architectural innovations and how they influenced the present-day skyline

$84 $50

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Take in Chicago's Best Holiday Lights on a BYOB Trolley

BYOB Holiday Trolley Tour

Matilda's

Climb aboard a vintage trolley and marvel at some of the Windy City’s cheeriest holiday sights while sipping on BYO beverages

$65 $45

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$12 for a Two-Hour Guided Walking Tour from the Chicago Architecture Foundation ($20 Value)

Chicago Architecture Foundation

CAF Shop & Tour Center

Stroll past Chicago icons designed by renowned architects such as Frank Lloyd Wright, Daniel Burnham, Louis Sullivan, and Frank Gehry

$20 $12

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$24 for a Chicago History Tour in the Pedway for Two from Chicago's Finest Tours (Up to $50 Value)

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 $24

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$69 for a Segways at Sunset Tour for Two from Bike and Roll Chicago (Up to $138 value)

Bike and Roll Chicago

Millennium Park

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

$138 $69

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Walking Tour from WendyCity (Up to 55% Off). Two Options Available.

WendyCity

Multiple Locations

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

$50 $23

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

Great Food 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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Arcade/Bar Tournament League from BUCKit List Events - Individual or Team Registration (Up to 68% Off)

BUCKit List Events

Multiple Locations

Three-person teams go head-to-head in seven-week arcade tournament with one week of playoffs

$80 $27

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"Speakeasy" Social Game Experience for One, Two, Four, or Eight at Waxwing Puzzle Co. (Up to 57% Off)

Waxwing Puzzle Co.

Lincoln Square

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

$40 $20

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Running Tours of Downtown Chicago from Chicago Running Tours & More (Up to 55% Off)

Chicago Running Tours & More

Central Chicago

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

$32 $15

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$37 for a Two-Hour Segway Tour of Downtown Chicago from Segway Experience of Chicago (Up to $65 Value)

Segway Experience of Chicago

The Loop

Atop a latest-generation Segway PT, guests coast past Buckingham Fountain and Millennium Park, occasionally pausing for photo ops

$65 $37

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40-Minute Ride in a Extra 300L Stunt Airplane or T-6 Texan Trainer Warplane from Gauntlet Warbirds (41% Off)

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

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Select Local Merchants

Rotorzen instills students with the skills and savvy needed to command the open-air cockpit of a powered parachute. Certified instructors nurse knowledge over 60 minutes of pre-flight training, teaching aspiring daredevils how to handle instrumentation and sneak up on cirrus clouds from behind. Students next take to the skies for 30 minutes of turbine-charged cruising as they skim over and sail through the air above the Lansing Municipal Airport. Flight lessons depend upon wind conditions and are offered Friday evenings, Saturday mornings, Saturday evenings, and Sunday mornings. While powered parachutes accommodate only one pilot at a time, individuals can bring along fellow flyers to join in on the acrobatic antics. All flight time can be applied toward FAA sport pilot certification and subsequent opportunities to tickle the moon into sneezing green cheese.

6640 South Cicero Avenue
Bedford Park,
IL
US

Founder Amanda Scotese, an avid traveler and freelance writer for Rick Steves's renowned travel guides, delegates sure-footed guides to lead sightseers to iconic landmarks and down the back alleys and lesser-known nooks of the Windy City. Tours probe the ins and outs of the Chicago's neighborhoods, such as the Loop, where they fill eyes with the sights of world-renowned architecture and minds with the secrets of the Pedway, an underground walkway that connects buildings throughout the business district with the Ninja Turtles' lair. The Historic Chicago Bar Tour, born of Chicago Detours' desire to spread knowledge of the city's entertainment history, takes tour-goers to three historic bars in an exploration of how the city had fun. Private group Jazz, Blues & Beyond tours explore historic neighborhoods on the North and South sides, and include diversions such as harmonica lessons from a bona fide blues blower. Chicago Detours also offers private-group tours for birthdays, family reunions, and corporate team-building exercises. Private group tour options also include Meat History of Fulton Market and Chicago Neighborhoods and Cultural Diversity.

10 South Dearborn Street
Chicago,
IL
US

Owner Valerie Beck and her team of chocophile tour guides lead guests on walking tours of Chicago’s historical bakeries and chocolatiers, narrating the history of beloved sweets while walking an easy route through vistas of Chicago’s stunning architectural heritage. While snacking on samples of sweets, guests learn about chocolate’s storied history, the cupcake’s rise to prominence, and how to guess the flavor of filling inside Oompa Loompas by sight. Tours convene throughout Chicago’s many neighborhoods, giving guests a sneak peek into Chicago's signature confections, boutique shops, and mobile sweet-vending trucks. The chocolate or cupcake jaunts provide the perfect setting for a girls’ day out or bachelorette party, showing tour-goers the sweeter side of the city without getting caught in construction sites of shoddily built gingerbread houses.

500 North Michigan Avenue
Chicago,
IL
US

Chicago Chinese Cultural Institute was created with a mission in mind: to conduct programs and events that promote Chinese language and culture, and to facilitate relationships between Chinese and American cultures. Chicago Chinese Cultural Institute offers corporate services such as cross-cultural and language training, helping bridge any gaps between employees who might travel between countries or consider dipping hands in a vat of honey before sealing a business deal. Chicago Chinese Cultural Institute also hosts various tours: walking tours guide explorers through Chinatown, exploring architectural fixtures and businesses of the area, whereas food tours entreat guests to visit several restaurants and shops, sampling appetizers, entrees, and teas.

2109B S China Pl
Chicago,
IL
US

Led by a team of knowledge-packed guides, Joyce Walks Chicago introduces out-of-towners and natives alike to the Second City's historic hoods during a full schedule of weekly walking tours. Each unique jaunt showcases a variety of hidden gems and well-known attractions, such as the Lincoln Park and Old Town tour, which weaves along the lakefront, or the Loop Art & Architecture tour, which lets participants examine The Picasso and solicit autographs from famous skyscrapers. The company's well-researched repertoire also includes seasonal treks that unveil some of the city's most decorated dwellings, affording tour takers the chance to absorb winter's twinkling lights and summer's stickball games between neighborhood pigeons.

4001 North Clark Street
Chicago,
IL
US

It's safe to say that Frank Lloyd Wright is a household name, partly because he put his name on so many houses. The sites overseen by the Frank Lloyd Wright Trust receive as many as 150,000 visitors a year—tangible proof that the visionary's impact on architecture, design, and culture remains alive and well. To ensure that legacy continues, the Chicago-based nonprofit maintains several of Wright's buildings and hosts various educational programs.

  • Size: five Frank Lloyd Wright architectural sites throughout Chicago and Oak Park
  • Crown Jewel: the Frank Lloyd Wright home and studio in Oak Park, where the visionary spent the first 20 years of his career
  • Eye Catcher: The Rookery Building's Light Court, a luminous Chicago landmark at the center of the Financial District
  • Don't Miss:Unity Temple. Made of exposed and reinforced concrete, this is the only surviving public building from Wright's Prairie Period.
  • Instead of Squinting Over Wright's Blueprints: see the trust's sites in person via guided walking, bus, and bike tours
  • Special Programs: Trust sites host concerts, arts and crafts workshops, and other programs for both kids and adults
5757 South Woodlawn Avenue
Chicago,
IL
US

Groupon Guide