Sightseeing in Chicago


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

Multiple Locations

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

$60 $35

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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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Island Party Boat: $25 for a 90-Minute Weeknight Cruise for One from Island Party Boat ($49.50 Value)

$25 for a 90-Minute Weeknight Cruise for One from Island Party Boat ($49.50 Value)

Island Party Boat

Central Chicago

Enjoy drink specials, music, and views of the Chicago skyline on an island-themed cruise

$49.50 $25

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

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

Chicago History Museum

Multiple Locations

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

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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Challenge Nation: $25 for Entry to Chicago Challenge: The Ultimate Urban Scavenger Race on July 11, 2015 ($55 Value)

$25 for Entry to Chicago Challenge: The Ultimate Urban Scavenger Race on July 11, 2015 ($55 Value)

Challenge Nation

Bar Louie South Loop

Teams race to solve clues and strategize to win cash prizes and awards during urban race; music and drink specials at post-race party

$55 $25

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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: $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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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

Chicago

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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WendyCity: Walking Tour from WendyCity (Up to 51% Off). Two Options Available.

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

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

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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Chicago Running Tours & More: Running Tours of Downtown Chicago from Chicago Running Tours & More (Up to 55% Off)

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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Chicago Film Tour: Chicago or Blues Brothers Film Tour for Two from Chicago Film Tour (Up to 50% Off)

Chicago or Blues Brothers Film Tour for Two from Chicago Film Tour (Up to 50% Off)

Chicago Film Tour

Near North Side

Bus trips steer past famous locations from Blues Brothers movies or other films shot in Chicago

$60 $30

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Captain Al's Charter Boat Fleet: $500 for a Two-hour Chartered Party Cruise on Lake Michigan for Up to Six from Captain Al's Charter Boat Fleet ($976 Value)

$500 for a Two-hour Chartered Party Cruise on Lake Michigan for Up to Six from Captain Al's Charter Boat Fleet ($976 Value)

Captain Al's Charter Boat Fleet

Burnham Harbor

Party cruise on Lake Michigan where you can enjoy views of the magnificent skyline aboard a 32 foot powerboat

$976 $500

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Second City Tours: Beer and Bacon Tour, Wine and Cheese Walk, Pizza Parade, or Cupcake Crawl from Second City Tours (Up to 56% Off). Six Options Available.

Beer and Bacon Tour, Wine and Cheese Walk, Pizza Parade, or Cupcake Crawl from Second City Tours (Up to 56% Off). Six Options Available.

Second City Tours

Near North Side

Enjoy beer and bacon pairings. wine and cheese, pizza, or cupcakes during fun food tours

$100 $49

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Select Local Merchants

  • Chicago Detours
    On this walking tour, guides talk about Chicago’s entertainment history related to Prohibition, the Jazz Age, and theater. Though drinks are not included, guests will be able to stop for a sip at several legendary taverns.
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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
  • Art de Triumph
    At Art de Triumph, local artist Nancie King Mertz showcases her original paintings and pastels and outfits clients' masterpieces in custom frames. Much like the courtroom artist at Rod Blagojevich's trial, Mertz often draws inspiration from iconic Chicagoan figures, rendering portraits including The Bean (also known as Cloud Gate) and the Wrigley Building. The Chicago Convention & Tourism Bureau named Mertz the Artist of the Year from 2005 through 2007, acknowledging her expertise with watercolor, oil, and pastel. In addition to ready-wear wall art, Art de Triumph deals in custom frames, helping clients select and customize matting and framing for photos, posters, and other important memorabilia such as the CTA card used to travel to the studio.
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    2938 N Clark St
    Chicago, IL US
  • Chicago Chinese Cultural Institute
    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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    2109B S China Pl
    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

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