Sightseeing in Chicago


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

Island Party Boat

Tiki 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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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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$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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$20 for $40 worth of Drinks at O 'Donnell's pub (Up to 40% Off)

O 'Donnell's pub

O 'Donnell's pub

Enjoy cold beers and cocktails and friendly conversation at this neighborhood corner pub

$20 $12

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

Chicago History Museum

The Chicago History Museum

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

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

360 Chicago at The John Hancock Center

John Hancock Observatory

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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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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$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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Entry to Urban Scavenger Hunt for One, Two, or Four from CityScape Adventures (Up to 71% Off)

CityScape Adventures

Moe's Cantina River North

Five-hour scavenger hunt takes participants through 12 challenges that encourage them to explore the city while testing their mettle

$60 $19

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$59 for Scavenger Dash for a Team of Two from Sierra Adventure Sports on Saturday, June 13 ($127.59 Value)

Sierra Adventure Sports

Citizen Bar

Teams of two traverse the streets of Chicago as they find clues, collect items, take pictures, and complete challenges

$127.59 $59

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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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$42 for a Chicago Bus Tour for Two from Chicago's Finest Tours ($70 Value)

Chicago's Finest Tours

Chicago

Explore some of Chicago’s 200 vibrant neighborhoods through the North and South Sides while riding inside of an enclosed motor coach

$70 $42

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Explore Lincoln Park's Monuments with a Local Author

Tour Lincoln Park's Monuments

Krista August

Author of award-winning book “Giants in the Park” leads walking participants on a tour of Lincoln Park’s monumental art

$20

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

Chicago Crime Tours

Chicago Crime Tours

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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Select Local Merchants

  • 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
  • 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 North Lincoln Avenue
    Chicago, IL US

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