Sightseeing in Chicago


General Admission or Multiple Visits at 360 CHICAGO (Formerly John Hancock Observatory) (Up to 32% Off)

360 Chicago at The John Hancock Center

Near North Side

94 floors up, take in stunning panoramas of Chicago and it’s sky-high architecture bordered by sparkling Lake Michigan

$38 $26

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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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$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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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 WWII

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

Chicago's Finest Tours

Chicago's Finest River Walk Tour

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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Admission for 2 or 4, or One- or Two-Year Family Membership to Peggy Notebaert Nature Museum (Up to 50% Off)

Peggy Notebaert Nature Museum

Peggy Notebaert Nature Museum

Nature museum hosts living and educational exhibits on the natural world including a butterfly haven and a native prairie.

$18 $11

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Select Local Merchants

  • Pick up location
    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
  • CAF Shop & Tour Center
    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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    4001 North Clark Street
    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 N Michigan Ave.
    Chicago, IL US
  • Chicago Photography Academy
    Faster than Anne Geddes can dress a baby as a flower, you could sign up at the Chicago Photography Academy. Choose from one-day, two-day or four-week digital photography classes whether you got your camera last week or last decade. They even offer certificate programs for those who want to earn a living by being creative. Learn the basics or specialize in particular areas like wedding photography and advance portraiture or find out more about using programs like Adobe Lightroom. And if you can't meet in the flesh, consider an online class. With Chicago Photography Academy, you'll have everyone around you begging to say 'Cheese' for their next photo.
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    3047 N Lincoln Ave.
    Chicago, IL US
  • Hubbard Street Dance Chicago
    Back in 1974, Lou Conte Dance Studio was nothing more than a twinkle in Claire Bataille's eye. Nearly 40 years and a slew of international acclaim later, the studio has become a pillar of the Chicago dance community. Today, Bataille—who earned the Ruth Page Award for Outstanding Dancer— and her staff lead more than 70 dance and fitness classes every week for teens, adults, beginners, and professionals. Their regular workshops delve into the nuances and history of dance, enhancing the curriculum with focused lessons and special lectures on the dangers of carelessly discarding banana peels.
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    205 E Randolph St
    Chicago, IL US

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