Sightseeing in Chicago


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

View Deal

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

View Deal

Seadog Cruises: Lakefront Speedboat Tour, Thrill Ride, or Architectural Tour from Seadog Cruises (Up to 43% Off)

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

View Deal

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

View Deal

Chicago History Museum: Visit for One, Two, or Four to the Chicago History Museum (Up to 48% Off)

Visit for One, Two, or Four to the Chicago History Museum (Up to 48% 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 $8

View Deal

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

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

APR Pullman Porter Museum

Chicago

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

$50 $25

View Deal

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

View Deal

Waxwing Puzzle Co.: "Speakeasy" Social Game Experience for One, Two, Four, or Eight at Waxwing Puzzle Co. (Up to 57% Off)

"Speakeasy" Social Game Experience for One, Two, Four, or Eight at Waxwing Puzzle Co. (Up to 57% Off)

Waxwing Puzzle Co.

Ravenswood

Players take part in a role-playing event that is set in the prohibition era and pulls from mob folklore

$40 $20

View Deal

Slice of Chicago Pizza Tours: Chicago Pizza Walking Tour for Two or Four from Slice of Chicago Pizza Tours (Up to 54% Off)

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

View Deal

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

View Deal

Island Party Boat: $65 for a Three-Hour Thirsty Thursday Margarita Cruise from Island Party Boat ($125 Value)

$65 for a Three-Hour Thirsty Thursday Margarita Cruise from Island Party Boat ($125 Value)

Island Party Boat

Central Chicago

Enjoy a margarita, salsa music, and views of the Chicago skyline on an island-themed cruise

$125 $65

View Deal

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

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

Tiki Boat Chicago

Chicago

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

View Deal

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

View Deal

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

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

View Deal

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

View Deal

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

$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

View Deal

Chicago Loop Bridges: Explore the Kinetics of Chicago's Massive Moving Bridges

Explore the Kinetics of Chicago's Massive Moving Bridges

Chicago Loop Bridges

West Loop

Walk along the Chicago River with a retired civil engineer who explains the history and architecture of the city’s movable bridges

$15

View Deal

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

View Deal

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

$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

View Deal

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.
    Read More
    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.
    Read More
    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.
    Read More
    2938 N Clark St
    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.
    Read More
    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.
    Read More
    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.
    Read More
    401 North Michigan Avenue
    Chicago, IL US

Groupon Guide

Advertisement