Sightseeing in Chicago


Chicago Chinese Cultural Institute: Discover Chinatown Walking Tour for Two or Four from the Chicago Chinese Cultural Institute (Up to 52% Off)

Discover Chinatown Walking Tour for Two or Four from the Chicago Chinese Cultural Institute (Up to 52% Off)

Chicago Chinese Cultural Institute

Armour Square

Chinatown walking tour showcases historical landmarks and great restaurants and teahouses on a 90-minute, 5-block jaunt

$20 $10

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City Winery Chicago: City Winery Chicago at City Winery Chicago

City Winery Chicago at City Winery Chicago

City Winery Chicago

City Winery

$10 $3.75

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Island Party Boat: $65 for a Three-Hour Thirsty Thursday Margarita Cruise from Island Party Boat ($125 Value)

$65 for a Three-Hour Thirsty Thursday Margarita Cruise from Island Party Boat ($125 Value)

Island Party Boat

Central Chicago

Enjoy a margarita, salsa music, and views of the Chicago skyline on an island-themed cruise

$125 $65

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

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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Chicago History Museum: Visit for One, Two, or Four to the Chicago History Museum (Up to 48% Off)

Visit for One, Two, or Four to the Chicago History Museum (Up to 48% Off)

Chicago History Museum

Chicago

Chicago museum brings history to life with 22 million artifacts & topical exhibits, including a look at railroad workers during WWI

$14 $8

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Seadog Cruises: Lakefront Speedboat Tour, Thrill Ride, or Architectural Tour from Seadog Cruises (Up to 43% Off)

Lakefront Speedboat Tour, Thrill Ride, or Architectural Tour from Seadog Cruises (Up to 43% Off)

Seadog Cruises

Navy Pier

Speedboats zip past famed Chicago landmarks along the lakefront and river; informative narration on city’s history and architecture

$32.42 $20

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Weird Chicago Tours: Three-Hour Historical Bus Tour for Two or Four from Weird Chicago Tours (Up to 39% Off)

Three-Hour Historical Bus Tour for Two or Four from Weird Chicago Tours (Up to 39% Off)

Weird Chicago Tours

Pick up location

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

$70 $45

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The Adler Planetarium: One-Year Individual or Family Membership at the Adler Planetarium (Up to 39% Off)

One-Year Individual or Family Membership at the Adler Planetarium (Up to 39% Off)

The Adler Planetarium

Museum Campus

See the Chicago night sky as it looked in 1913, view a Mars rover replica, and explore the makeup of the Universe—from galaxies to atoms

$89 $59

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Tall Ship Adventures of Chicago: 75-Minute Sailing Tour on Tall Ship "Windy" (Up to 33% Off). Three Options Available.

75-Minute Sailing Tour on Tall Ship "Windy" (Up to 33% Off). Three Options Available.

Tall Ship Adventures of Chicago

Navy Pier

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

$30 $20

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

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

Waxwing Puzzle Co.

Ravenswood

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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Tiki Boat Chicago: $349 for a Three-Hour Weekday Tiki-Boat Cruise from Tiki Boat Chicago ($705 Value)

$349 for a Three-Hour Weekday Tiki-Boat Cruise from Tiki Boat Chicago ($705 Value)

Tiki Boat Chicago

Chicago

Tiki boats with onboard water slides, barbecue grill & seating for up to 12 cruise to sites such as the Chicago River & 63rd Street Beach

$705 $349

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Urban Dare: $45 for an Urban Dare Adventure Race for a Two-Person Team (Up to $90 Value)

$45 for an Urban Dare Adventure Race for a Two-Person Team (Up to $90 Value)

Urban Dare

Bar Louie River North

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

$90 $45

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Cover Your Bases: $12 for Cover Your Bases Baseball-Themed Pub Crawl by Festa Parties on Saturday, May 9 ($22 Value)

$12 for Cover Your Bases Baseball-Themed Pub Crawl by Festa Parties on Saturday, May 9 ($22 Value)

Cover Your Bases

Murphy's Bleachers

Partiers stop at 12 bars and celebrate all things baseball

$22 $12

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Chicago Hauntings Ghost Tour: Haunted "Dead and Undead" Walking Tour for One, Two, or Four from Chicago Hauntings (44% Off)

Haunted "Dead and Undead" Walking Tour for One, Two, or Four from Chicago Hauntings (44% Off)

Chicago Hauntings Ghost Tour

Near North Side

Get an inside peek in Chicago’s dark and sinister past with a haunted walking tour

$34 $19

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Bike and Roll Chicago: $35 for a Bike and Yoga Tour for One from Bike and Roll Chicago ($60 Value)

$35 for a Bike and Yoga Tour for One from Bike and Roll Chicago ($60 Value)

Bike and Roll Chicago

Millenium Park

Bike down the Lakefront Trail to various parks, where the surroundings will lend serenity to Vinyasa yoga classes

$60 $35

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Bike and Roll Chicago: $69 for a Bike Tour and Tasting for Two at Lagunitas Brewing Co. from Bike and Roll ($138 Value)

$69 for a Bike Tour and Tasting for Two at Lagunitas Brewing Co. from Bike and Roll ($138 Value)

Bike and Roll Chicago

Millenium Park

Guests bike Chicago’s historic neighborhoods, tasting dishes from popular restaurants, ending with tour, tasting at Lagunitas Brewing Co.

$138 $69

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Chicago Loop Bridges: Explore the History of Chicago's Massive Downtown Bridges

Explore the History of Chicago's Massive Downtown Bridges

Chicago Loop Bridges

The Loop

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

$20

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

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

Slice of Chicago Pizza Tours

Chicago

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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Chicago Line Cruises: $59 for a 90-Minute Architectural Boat Tour for Two from Chicago Line Cruises ($84 Value)

$59 for a 90-Minute Architectural Boat Tour for Two from Chicago Line Cruises ($84 Value)

Chicago Line Cruises

Near North Side

Professional docents tell the stories behind over 50 “cloud busters” and narrate historical events that influenced the present-day skyline

$84 $59

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Select Local Merchants

  • Chicago Detours
    facet: Main type: Traditional locale: en_US title: Chicago Detours facet_type_id: bbcf7c70-5f37-1032-8e47-ad35deb884bd html_text: 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.
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    10 S Dearborn St.
    Chicago, IL US
  • Art Institute of Chicago
    The Art Institute of Chicago was founded as both a museum and school for the fine arts in 1879, a critical era in the history of Chicago as civic energies were devoted to rebuilding the metropolis that had been destroyed by the Great Fire of 1871. Its first collections consisting primarily of plaster casts, the Art Institute found its permanent home in 1893, when it moved into a building, constructed jointly with the city of Chicago for the World's Columbian Exposition, at the intersection of Michigan Avenue and Adams Street. That building, its entry flanked by the two famous bronze lions, remains the "front door" of the museum even today. In keeping with the academic origins of the institution, a research library was constructed in 1901; eight major expansions for gallery and administrative space have followed, with the latest being the Modern Wing, which opened in 2009. The permanent collection has grown from plaster casts to nearly 300,000 works of art in fields ranging from Chinese bronzes to contemporary design and from textiles to installation art. Together, the School of the Art Institute of Chicago and the museum of the Art Institute of Chicago are now internationally recognized as two of the leading fine-arts institutions in the United States.
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    111 S Michigan Ave
    Chicago, IL US
  • Weird Chicago Tours
    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.
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    600 N Clark St.
    Chicago, IL US
  • Chicago Chinese Cultural Institute
    facet: Main type: Traditional locale: en_US title: Chicago Chinese Cultural Institute facet_type_id: 9bc689e0-5f38-1032-b2cd-ff09c7258e8f html_text: '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.'
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    2121B South China Place Chicago, IL 60616
    Chicago, IL US
  • Chicago Architecture Foundation
    The Chicago Architecture Foundation works to promote the city of Chicago as a major architectural center. Additionally, they provide a forum for professionals who are interested in or involved in architectural design. The Foundation encourages citizens to become involved in every facet of architecture including the design and engineering phases. The organization was formed in 1966 by concerned members of the community who were dedicated to preserving the Glessner House from demolition. Their successful efforts not only saved the private residence designed by H.H. Richardson, but also led to the founding of the organization. They offer regular exhibits and educational programs for adults and children and do accept all types of donations. They are located at 224 S. Michigan Avenue in Chicago, Illinois and continue to work in the community to preserve beautiful structures and educate the public on the intrinsic value of amazing architecture.
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    224 S Michigan Ave.
    Chicago, IL US
  • Chicago Chocolate Tours
    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.
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    500 North Michigan Avenue
    Chicago, IL US

Groupon Guide