Tours in Chicago


Second City Tours: Cupcake Crawl for One, Two, or Four from Second City Tours (Up to 60% Off)

Cupcake Crawl for One, Two, or Four from Second City Tours (Up to 60% Off)

Second City Tours

Water Tower Place

The city’s favorite cupcake hot spots are visited during this tour: Sprinkles, Sacred Grounds, More, and Crumbs

$50 $23

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Chicago Hauntings Ghost Tour: Haunted "Dead and Undead" Walking Tour for One, Two, or Four from Chicago Hauntings (51% Off)

Haunted "Dead and Undead" Walking Tour for One, Two, or Four from Chicago Hauntings (51% 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 $17

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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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The Mystic Blue: Mystic Blue Buffet Cruises at The Mystic Blue

Mystic Blue Buffet Cruises at The Mystic Blue

The Mystic Blue

Near North Side

$89.63 $61.52

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

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

Island Party Boat

Central Chicago

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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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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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

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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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

Near North Side

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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Scoot for Good: 4- or 8-Hour Scooter Rental for One or Two from Scoot for Good (Up to 53% Off)

4- or 8-Hour Scooter Rental for One or Two from Scoot for Good (Up to 53% Off)

Scoot for Good

Meeting point

Sight-see around Chicago on easy-to-operate scooters that come with instruction overview

$79 $45

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Chicago Crime Tours: Tour by Bus for Two or Four from Chicago Crime Tours (Up to 47% Off)

Tour by Bus for Two or Four from Chicago Crime Tours (Up to 47% 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 $45

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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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Sidewalk Food Tours of Chicago: Walking Food Tour for One or Two from Sidewalk Food Tours of Chicago (Up to 37% Off)

Walking Food Tour for One or Two from Sidewalk Food Tours of Chicago (Up to 37% Off)

Sidewalk Food Tours of Chicago

Multiple Locations

Enjoy a roving lunch of five different tastings while learning about the history and culture of either River North or Wicker Park

$55 $35

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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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The Plant: Sustainable-Food Facility Tour for Two or Four at The Plant (Up to 45% Off)

Sustainable-Food Facility Tour for Two or Four at The Plant (Up to 45% Off)

The Plant

Back of the Yards

Self-sustaining urban facility houses a hydroponic farm, nonprofit education and research center, and various food-production businesses

$20 $12

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Chicago's Finest Tours: Sightseeing Tours for Two from Chicago's Finest Tours (Up to 52% Off)

Sightseeing Tours for Two from Chicago's Finest Tours (Up to 52% Off)

Chicago's Finest Tours

Multiple Locations

Tours take guests along Chicago’s historic River Walk, around the Loop, or to a hearty brunch buffet

$60 $29

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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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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

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Select Local Merchants

  • 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
  • A Taste of Hyde Park
    facet: Main type: Traditional locale: en_US title: A Taste of Hyde Park facet_type_id: 26be5e30-5f2d-1032-bf97-5615d5fccde0 html_text: 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, cafés, 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
  • Dream Adventures USA
    Dream Adventure USA owner Richard Arnold began ballooning as a way to advertise his jewelry business, but quickly discovered customers were as excited about skimming the treetops as they were about adorning themselves in karats. Now, accompanied by his wife of more than 18 years, their children, and a team of dedicated crewmembers, Arnold takes passengers of all ages on memorable airborne adventures in 10 states. Upon arrival at the takeoff location, passengers watch the giant orbs inflate, then step into baskets that hold as many as 16 people. The licensed pilots fire up vessels to soar as high as several thousand feet, giving participants an unobstructed and unique view of the surrounding scenery. After landing, each flight experience finishes with a champagne toast or celebratory Gatorade shower.
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    600 North Wabash 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
  • Chicago Crime Tours
    facet: Main type: Traditional locale: en_US title: Chicago Crime Tours facet_type_id: afba2ab0-5f3d-1032-bf65-98257e356da8 html_text: Chicago’s beautiful architecture and pristine parks stretch like a thin, deceptively pretty layer of varnish over the city’s storied criminal history. The guides at Chicago Crime Tours peel back the façade to reveal the city’s darkest days, replete with visits to crime scenes and tales of some of Chicago’s most dastardly villains. Groups explore the hideouts of Al Capone and bullet holes left in the wake of mob shootouts. The guides’ catalog of criminal knowledge reaches all the way back to city’s infancy in the 19th century and includes such tales as the Saint Valentine’s Day Massacre and the great baby-rattle heist of 1870.
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    163 E Pearson St.
    Chicago, IL US

Groupon Guide