Tours in Forest Park

Two or Four Tickets to a Tour of the Frank Lloyd Wright Home and Studio or Frederick C. Robie House (50% Off)

Frank Lloyd Wright Trust

Multiple Locations

Guided tour of one of two local architectural marvels that stand as seminal works in Frank Lloyd Wright’s legendary career

$34 $17

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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

Aurora

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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Wine and Cheese Tour of Chicago with 12 Tastings and Pairings from Great Food Tours (Up to 58% Off)

Great Food Tours

Near North Side

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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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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Fireball Santa Crawl for One, Two, or Four with Breakfast Buffet on Saturday, December 20 (Up to 51% Off)

Fireball Santa Crawl

Chicago

Start the day at Bar Louie with an egg and sausage buffet, then hit up four other watering holes for specials on Fireball shots and beer

$20 $12

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Four-Hour Inside Chicago Grand Tour by Bus for Two or Four from American Sightseeing Chicago (Up to 50% Off)

American Sightseeing Chicago

Palmer House Hilton, Ground Floor Gift Shop

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

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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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Chicago Pizza Walking Tour for Two or Four from Slice of Chicago Pizza Tours (Up to 54% Off)

Slice of Chicago Pizza Tours

Near North Side

2-hour, 1.2-mile walking tour hits several pizzerias like Pizzeria Uno and Giordano’s in River North to sample pizza and learn its history

$90 $44

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Architecture Tour by Boat for Two Adults from Shoreline Sightseeing

Shoreline Sightseeing

Multiple Locations

75-minute tours explore the history of more than 40 architectural landmarks while cruising down the branches of the Chicago River

$71.12 $49

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Tour by Bus for Two or Four from Chicago Crime Tours (Up to 49% Off)

Chicago Crime Tours

Chicago

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

$79.90 $42

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Walking Tour from WendyCity (Up to 51% 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 $25

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Arcade/Bar Tournament League from BUCKit List Events - Individual or Team Registration (Up to 55% Off)

BUCKit List Events

Multiple Locations

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

$80 $39

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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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Eat Hyde Park or Sweet Hyde Park Tour for 1, 2, or 4 from A Taste of Hyde Park Walking Tours (Up to 56% Value)

A Taste of Hyde Park

Multiple Locations

Guests sample hot dogs at Bergstein’s NY Deli, samosas at Rajun Cajun, and fudge at Kilwin’s

$50 $25

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$58 for a Ghost Investigation Tour for Two from Chicago Ghost Investigations ($116 Value)

Chicago Ghost Investigations

Pilsen

After a crash course in ghost hunting, small teams use tools to explore and communicate with ghosts of Al Capone’s underworld

$116 $58

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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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"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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Two-Hour Walking Ghost Tour of Aurora or Naperville for Two or Four from Haunted Hometowns (Up to 51% Off)

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

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Select Local Merchants

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

The labyrinthine streets of Chicago contain a wealth of bizarre secrets?it just takes the right person to find them. That's where the team of quirky guides behind Weird Chicago Tours come in. As a diverse group of amateur detectives, history buffs, and ghost-hunters, they've acquired the knowledge and experience necessary to lead others into the city's darkest corners. At some stops, passengers disembark and venture inside for a closer look.

Weird Chicago Tours is always devising new tour themes, such as the Roaring '20s Tour: an adults-only exploration of Prohibition and 1920s gangster activity through visits to a former brothel district and a series of bars. The Haunted History Tour recounts some of Chicago's most unusual ghost stories and stops at areas of reported paranormal activity. Other tours prowl sites tied to Al Capone's notorious career and the St. Valentine's Day massacre or grisly crime scenes straight out of the novel Devil in the White City.

600 N Clark St.
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

Shoreline Sightseeing has been whisking passengers along Lake Michigan since 1939. Traveling down the reverse-engineered Chicago River, Shoreline?s architecture tours explore the history of the city?s landmark buildings?from the Great Fire of 1871 to the work of famed architects Mies van der Rohe and Jeanne Gang. Colorful bursts illuminate the sky during fireworks cruises, and nighttime tours allow for glimpses of lit-up buildings. Classic lake tours drift into Lake Michigan, giving passengers a chance to espy the whole city, and water taxis connect visitors from one destination to the next, speeding between Navy Pier, the Museum Campus, Michigan Ave., and the Willis Tower.

401 N Michigan Ave.
Chicago,
IL
US

Groupon Guide