Sightseeing in Chicago

$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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$39 for a Two-Hour Wednesday-Night Fireworks Cruise from Island Party Boat ($75 Value)

Island Party Boat

Chicago

Take in fireworks lighting up the Chicago skyline on an island-themed 50-foot boat equipped with a sundeck, lounge, and premium sound system

$75 $39

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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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"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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General, Family, or Friend Sponsor Annual Membership to the APR Pullman Porter Museum (50% Off)

APR Pullman Porter Museum

Far South Chicago

Museum celebrates the victories of the nation’s first African-American labor unions and the history of African-American railroad workers

$50 $25

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Visit for One, Two, or Four to the Chicago History Museum (Up to 50% Off)

Chicago History Museum

Lincoln Park

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

$14 $7

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

Great Food Tours

Chicago

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

$50 $25

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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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One or Six BeadQuest Mardi Gras Pub Crawl Tickets from Festa Parties (Up to 50% Off)

Festa Parties

Chicago

Enjoy Louisiana style food and a quest for beads with friends during a fun-filled pub crawl through Wrigleyville

$22 $12

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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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$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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Admission for Two or 1-Year Individual or Family Membership at International Museum of Surgical Science (50% Off)

International Museum of Surgical Science

Near North Side

More than 600 art pieces and 7,000 medical artifacts—including a working iron lung—trace the advancement of surgery throughout history

$30 $15

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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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Select Local Merchants

Today, millions of people live and thrive among the streets and skyscrapers of Chicago, but at one time the bustling metropolis had only one resident?namely, the city's apocryphal, somewhat legendary founder, Jean Baptist Point DuSable. A Haitian of French and African descent, DuSable was the first of Chicago's great African Americans, a company that includes the city's first black mayor, Harold Washington. In one of the DuSable Museum's standing exhibits, the Thomas Miller mosaics, portraits of DuSable and Washington peer out along with eight of the founding members of the museum?a constellation of lodestars reminding visitors to maintain Chicago's diverse heritage.

While the mosaics incorporate the museum's own story, other exhibits examine African American achievements of all kinds. Red, White, Blue & Black, for instance, examines the contributions of black men and women in the armed forces. In A Slow Walk to Greatness: The Harold Washington Story, visitors explore the nuances of the momentous campaign through memorabilia and more than 150 mayoral artifacts. An animatronic likeness of Mayor Washington himself even steps in to relay stories and first-hand accounts made possible by animatronic robots' ability to travel through time. In addition to the permanent exhibits, the museum also hosts musical performance, film festivals, and book signings that introduce members to more aspects of African American history, including the scholars who continue to uncover it.

740 E 56th Pl.
Chicago,
IL
US

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.

111 S Michigan Ave
Chicago,
IL
US

When entrepreneur Harold Pierce opened the first Harold’s Chicken Shack on Chicago’s South Side in 1950, his chefs fried chicken as it was ordered, filling customers' empty hands with baskets of fresh, piping-hot chicken in 12–15 minutes. Today, the chain of 62 restaurants peppered across the Midwest and Southwest continues the old tradition of rewarding patience with astonishingly delicious chicken. The long-standing shop specializes in a simple order—breaded chicken fried in a rich mix of vegetable oil and beef tallow for a home-cooked flavor. Chefs prep the chicken Chicago style by pouring a dash of sauce over the basket, which soaks into the white bread and crinkle fries that come with every order. Marked with the famed emblem of a cook chasing a chicken with a hatchet, the restaurant has saturated the city’s consciousness, earning a mention in Tucker Max’s I Hope They Serve Beer in Hell, an appearance in Kanye West’s music video Through the Wire, and its own chicken hologram projected over the skyline. Serious Eats sums up citywide sentiment for the chain: "When the words 'fried chicken' are uttered in Chicago, it’s a fair bet that the name Harold’s Chicken Shack will usually follow."

1134 W Washington Blvd
Chicago,
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

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

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.

224 S Michigan Ave.
Chicago,
IL
US

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