Sightseeing in Chicago


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

Tiki Party Boat

Island Party Boat

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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$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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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.

Waxwing Puzzle Company

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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$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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Visit for One, Two, or Four to the Chicago History Museum (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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General, Family, or Friend Sponsor Annual Membership to the APR Pullman Porter Museum (50% Off)

APR Pullman Porter Museum

A Philip Randolph Pullman Porter Museum

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

Great Food Tours New York

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

Tiki Boat Chicago

Chicago Tiki Boat Inc.

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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St. Patrick's Day Pub Crawl for Two or Four on March 13–17 from PubcrawlsChicago.com (Up to 56% Off)

Pub Crawl

Roadhouse 66

Three-day pub crawl celebrates St. Patrick’s Day with specials on domestic drafts and bottles, wells cocktails, and Irish whiskey shots

$40 $18

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

International Museum of Surgical Science

International Museum of Surgical Science Chicago

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

Chicago Running Tours

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

$32 $15

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$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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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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Visit for Two or Four, or Individual or Family Membership to Museum of Broadcast Communications (Up to 50% Off)

Museum of Broadcast Communications

Museum of Broadcast Communications

Artifacts and digitized recordings detail the history of radio and television; interactive station lets visitors anchor their own newscasts

$24 $12

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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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Select Local Merchants

  • Chicago Detours
    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
  • 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 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
  • Joyce Walks Chicago
    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.
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    Picasso statue in Daley Center 55 W. Washington
    Chicago, IL US
  • National Vietnam Veterans Art Museum
    Founded in 1982 with the mission of spreading an understanding of war's impact on the lives of soldiers, the National Veterans Art Museum showcases more than 2,000 works of art created by more than 255 veterans. The museum's oeuvre, which comprises paintings, photography, sculpture, and music, focuses on Vietnam but includes artwork inspired by all of America's wars. In addition to keep a permanent collection, the museum hosts rotating temporary exhibits that honor and remember veterans and keep the subject matter fresh. Visitors and members enjoy an active social calendar, stocked with events that feature live music and plays performed entirely with the NATO phonetic alphabet.
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    1801 S Indiana Ave
    Chicago, IL US
  • Shoreline Sightseeing
    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.
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    401 North Michigan Avenue
    Chicago, IL US

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