Tours in Chicago


Bike and Roll Chicago: $69 for a Segways at Sunset Tour for Two from Bike and Roll Chicago (Up to $138 value)

$69 for a Segways at Sunset Tour for Two from Bike and Roll Chicago (Up to $138 value)

Bike and Roll Chicago

Millenium Park

Easily maneuverable segway vehicles traverse the lakefront for views of the Chicago skyline, parks, and lakeside museums

$138 $69

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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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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

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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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Great Food Tours (Chicago): Drunk History of Chicago Tour at Four Pubs for One, Two, or Four from Great Food Tours (Up to 60% Off)

Drunk History of Chicago Tour at Four Pubs for One, Two, or Four from Great Food Tours (Up to 60% Off)

Great Food Tours (Chicago)

Chicago

Visit four local pubs to sample alcoholic beverages and shots, learn about the history of the city, and pick up some fake history too

$50 $25

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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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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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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

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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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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

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

Explore the Kinetics of Chicago's Massive Moving 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 movable bridges

$15

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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

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Urban Dare: $45 for an Urban Dare Adventure Race for a Two-Person Team (Up to $90 Value)

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

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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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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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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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

Chicago

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

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

Chicago Crime Tours

Near North Side

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

  • 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
  • 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 Sports Tour
    The bronze likeness of Michael Jordan—the Bulls' #23 and basketball's undisputed king—leaps into the air in front of the United Center, ascending into the annals of sports history. Across town, the sound of Babe Ruth's most famous homer rebounds off of the iconic walls of Wrigley Field. The Roman-meets-modern architecture of Soldier Field—where Walter Payton, Mike Ditka, and "The Fridge" grew to larger-than-life—straddles Chicago's lakefront. The resounding Black Sox scandal clashes with the victorious 2005 World Series Champs banners at U.S. Cellular Field, where the White Sox's famous exploding scoreboard towers above the Bridgeport neighborhood. During an air-conditioned bus ride, local comedians wax historic as tourists are brought within earshot and camera-shot of Chicago's proudest pro-sports franchises. The Chicago Sports Tour parades from the North to the South side, brushing shoulders with famous ballparks and weaving through more than a century of athletic anecdotes and civic pride. Augmented by laughs and entertainment, it reveals more than the brick-and-mortar façades of the famous stadiums. The guides bring each building to life with fascinating anecdotes, and rides from one stadium to the next cover neighborhoods such as Wrigleyville, Bridgeport, and Little Italy—where fans and players alike eat, drink, and argue about their favorite peanut vendors.:m]]
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    430 North Michigan Avenue
    Chicago, IL US
  • Sidewalk Food Tours of Chicago
    Sidewalk Food Tours of Chicago introduces tourists and locals to the Windy City's thriving food scene via deep-dish pizzas, hot dogs, and ethnic cuisine. Two neighborhoods in particular brim with famous restaurants and hidden eateries: Wicker Park and River North. On their streets, Sidewalk Food Tours of Chicago's local guides lead groups on walking explorations, pausing frequently to taste everything from cupcakes to Top Chef Masters winner Rick Bayless's Mexican cuisine. Food stands at the crossroads of each neighborhood's culture, and the guides use it as a jumping off point to discuss local history and architecture. They might spin tales of how Wicker Park was once a hotbed of European immigration or how River North accumulated a wealth that would make John D. Rockefeller's piggy bank tremble with envy.
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    222 W Merchandise Mart Plz.
    Chicago, IL US
  • A Taste of Hyde Park
    There's a lot more to Hyde Park than the prominent cultural and academic institutions here, and A Taste of Hyde Park is all about sharing those things. On walking tours that cover both iconic sites and little-known gems, they share a glimpse into the neighborhood's cuisine, culture, and history with insider tips along the way. Stops may include restaurants, caf?s, and sweet shops, where groups are greeted with small samples while learning more about the area. Additionally, A Taste of Hyde Park offers seasonal outings. Spooky, Halloween-themed tours, for one, recount some of the neighborhood's paranormal legends, including tales about lawyer Clarence Darrow's ghost at the Museum of Science and Industry and why it's always doing the jitterbug.
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    5221 S Harper Ct.
    Chicago, IL US
  • Chicago Food Planet Food Tours
    A truly innovative concept, Chicago Food Planet Tours offer a taste of Chicago like none other. If you are on a timeline and can’t decide which incredible restaurant to try, then try a bit of each with Chicago Food Planet. Pay a flat fee and they will escort you on a tasting menu like none other. Enjoy a small plate at every restaurant on the tour alongside demonstrations and explanations from knowledgeable chefs and staff. Tours are themed by Chicago districts from Chinatown to Gold Coast and Old Town. Don’t feel like being social? Book a private tour of your selection! An absolutely fantastic deal (you’re really getting a lot of bang for your buck here, guys) try out a tour with Chicago Food Planet.
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    830 North Michigan Avenue
    Chicago, IL US

Groupon Guide