Tours in Crestwood


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

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

Second City Tours

Near North Side

Head to River North for deep-dish pizza, Chicago-style hot dogs, Mike Ditka’s favorite italian-beef sandwiches, and dessert

$50 $23

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Best Tours: Cupcake Tour of Chicago with Six Tastings for One, Two, or Four from Best Tours (Up to 68% Off)

Cupcake Tour of Chicago with Six Tastings for One, Two, or Four from Best Tours (Up to 68% Off)

Best 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 $19

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Best Tours: Chocolate Tour of Chicago with Seven Tastings for One, Two, or Four from Best Tours (Up to 60% Off)

Chocolate Tour of Chicago with Seven Tastings for One, Two, or Four from Best Tours (Up to 60% Off)

Best Tours

Wrigley Building

Sample Aztec chocolate drinks, cupcakes, truffles, and chocolate donuts during two-hour chocolate tour along the Magnificent Mile

$50 $25

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Argus Brewery: 90-Minute Brewery Tour for Two, Four, or Six with Tastings, Snacks, and Glasses at Argus Brewery (Up to 63% Off)

90-Minute Brewery Tour for Two, Four, or Six with Tastings, Snacks, and Glasses at Argus Brewery (Up to 63% Off)

Argus Brewery

Roseland

During a 90-minute tour, guests learn about the historic origins of the brewery and the neighborhood while sampling craft brews

$30 $12

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I&M Canal National Heritage Corridor Civic Center Authority: Two Adult Tickets or a Family Pass to A River Thru History – The Des Plaines Valley Rendezvous  (Up to 50% Off)

Two Adult Tickets or a Family Pass to A River Thru History – The Des Plaines Valley Rendezvous (Up to 50% Off)

I&M Canal National Heritage Corridor Civic Center Authority

Willow Springs

The party sends visitors back in time to early Illinois, when fur trading was lucrative and the sound of cannon fire was a part of life

$25 $13

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McCormick Bridgehouse & Chicago River Museum: Bridge and Bridgehouse Tour for 1, 2, or 4 at McCormick Bridgehouse & Chicago River Museum (Up to 50% Off)

Bridge and Bridgehouse Tour for 1, 2, or 4 at McCormick Bridgehouse & Chicago River Museum (Up to 50% Off)

McCormick Bridgehouse & Chicago River Museum

The Loop

Museum guide showcases historic landmark bridgehouse with views of bridge gears, structure, and five-story tower along this riverwalk tour

$8 $5

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Disturbia Screams in the Park: $18.30 for Disturbia Screams in the Park Haunted House on October 4–November 1 ($28.15 Value). 11 Options Available.

$18.30 for Disturbia Screams in the Park Haunted House on October 4–November 1 ($28.15 Value). 11 Options Available.

Disturbia Screams in the Park

MB Financial Park at Rosemont

H.H. Holmes–themed haunted house features macabre scenes such as torture chambers, cannibalized victims, and the living dead

$28.15 $18.30

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The Spirit of Peoria: Riverboat Sightseeing Cruise or Overnight Excursion aboard The Spirit of Peoria (Up to 44% Off)

Riverboat Sightseeing Cruise or Overnight Excursion aboard The Spirit of Peoria (Up to 44% Off)

The Spirit of Peoria

Peoria

Enjoy the nostalgia of cruising the Illinois River Valley or the Mississippi River aboard an authentic paddlewheel driven riverboat

$32 $18

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Best Tours: Chicago Ghost Walk for One, Two, or Four from Best Tours (Up to 65% Off)

Chicago Ghost Walk for One, Two, or Four from Best Tours (Up to 65% Off)

Best Tours

Chicago

Tours visit haunted spots in search of apparitions, including the sites of the Iroquois Theatre fire and the Eastland shipwreck

$35 $17

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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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Inside Chicago Walking Tours: One or Two Youth or Adult Architecture Walking Tour Tickets from Inside Chicago Walking Tours (Up to 30% Off)

One or Two Youth or Adult Architecture Walking Tour Tickets from Inside Chicago Walking Tours (Up to 30% Off)

Inside Chicago Walking Tours

Chicago

A former teacher and improv comedian offers a slice of Chicago’s architecture and history on engaging walking tours

$20 $14

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Haunted Hometowns: Two-Hour Walking Ghost Tour of Aurora or Naperville for Two or Four from Haunted Hometowns (Up to 51% Off)

Two-Hour Walking Ghost Tour of Aurora or Naperville for Two or Four from Haunted Hometowns (Up to 51% Off)

Haunted Hometowns

Multiple Locations

Ghost-seekers clutch EMF meters on lantern-lit tours through historic and haunted sites as guides relate tales of local specters

$80 $39

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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

$159.80 $85

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Second City Tours: Chicago River Walk Architecture and History Walk for One, Two, and Four from Second City Tours (Up to 61% Off)

Chicago River Walk Architecture and History Walk for One, Two, and Four from Second City Tours (Up to 61% Off)

Second City Tours

The Loop

90-minute tour shares history and insight of the Chicago river region

$30 $14

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Fox River Distilling Company: Tour for Two or Four with Bloody-Mary Mix, Hats, and Rocks Glasses at Fox River Distilling Company (Up to 43% Off)

Tour for Two or Four with Bloody-Mary Mix, Hats, and Rocks Glasses at Fox River Distilling Company (Up to 43% Off)

Fox River Distilling Company

Geneva

Tour the distillery, which produces vodka, gin, and moonshine, and leave with bloody-mary mixes, hats, and rocks glasses

$47 $27

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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 57% Off)

Chicago Pizza Walking Tour for Two or Four from Slice of Chicago Pizza Tours (Up to 57% 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 $41

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Penrose Brewing Company: $15 for a Brewery Tour for Two or Four with Beer at Penrose Brewing Company ($20 Value)

$15 for a Brewery Tour for Two or Four with Beer at Penrose Brewing Company ($20 Value)

Penrose Brewing Company

Geneva

Learn about the Geneva brewery’s craft-beer brewing process and sip two 12 oz. beers

$20 $15

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

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

Best Tours

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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Second City Tours: Underground Pedway Tour for One, Two, or Four from Second City Tours (Up to 61% Off)

Underground Pedway Tour for One, Two, or Four from Second City Tours (Up to 61% Off)

Second City Tours

The Loop

90-minute walking tour takes guests through the underground walkways that connect a number of Chicago buildings

$30 $14

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

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

Best Tours

Chicago

Tours make six stops along Michigan Avenue, visiting the originator of deep-dish pizza and an eatery serving up Chicago-style hot dogs

$50 $25

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Best Tours: Italian Food Tour of Chicago with Five Tastings for One, Two, or Four from Best Tours (Up to 60% Off)

Italian Food Tour of Chicago with Five Tastings for One, Two, or Four from Best Tours (Up to 60% Off)

Best Tours

Chicago

Sample Chicago-style pizza, italian beef, and artisan products during a two-hour Italian-food tour along the Magnificent Mile

$50 $25

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Yacht Party Chicago: Halloween-Weekend Booze Cruise from Yacht Party Chicago (Up to 53% Off). Four Options Available.

Halloween-Weekend Booze Cruise from Yacht Party Chicago (Up to 53% Off). Four Options Available.

Yacht Party Chicago

Multiple Locations

Celebrate Halloween on a yacht that cruises into Lake Michigan with drinking and dancing to a DJ, followed by an after-party

$55.50 $26

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Smart Destinations: Two-Day All-Inclusive Go City Card Including Free Admission to Dozens of Popular Attractions

Two-Day All-Inclusive Go City Card Including Free Admission to Dozens of Popular Attractions

Smart Destinations

 

Card grants free admission to museums, tours, and attractions; save up to 55% off combined gate prices if purchased separately

$52.99 $49.50

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Best Tours: Wine and Cheese Tour of Chicago with 12 Tastings and Pairings from Best Tours (Up to 58% Off)

Wine and Cheese Tour of Chicago with 12 Tastings and Pairings from Best Tours (Up to 58% Off)

Best Tours

Near North Side

Stroll along the Magnificent Mile and through the Gold Coast as you sample 12 bites of cheese paired with sips of wine

$100 $49

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Second City Tours: Ghost Tour for One, Two, or Four from Second City Tours (Up to 61% Off)

Ghost Tour for One, Two, or Four from Second City Tours (Up to 61% Off)

Second City Tours

John Hancock Center

90-minute tour explores the tragic side of Chicago history with stops to locales said to be marked by paranormal activity

$30 $14

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Scoot for Good: 4- or 8-Hour Scooter Rental for One or Two from Scoot for Good (Up to 59% Off)

4- or 8-Hour Scooter Rental for One or Two from Scoot for Good (Up to 59% Off)

Scoot for Good

Meeting point

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

$79 $38

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Second City Tours: One, Two, or Four Tickets to the Wine and Cheese Walk from Second City Tours (Up to 59% Off

One, Two, or Four Tickets to the Wine and Cheese Walk from Second City Tours (Up to 59% Off

Second City Tours

Near North Side

Travel to three upscale restaurants and bars and sip nine or more samples of wine paired with assorted cheeses and small bites

$100 $49

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Second City Tours: One, Two, or Four Tickets to the Beer & Bacon Binge Food Tour from Second City Tours (Up to 59% Off)

One, Two, or Four Tickets to the Beer & Bacon Binge Food Tour from Second City Tours (Up to 59% Off)

Second City Tours

Near North Side

Explore three River North hotspots and sip craft beer paired with bacon snacks

$100 $49

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Second City Tours: Pizza Parade Tour for One, Two, or Four from Second City Tours (Up to 60% Off)

Pizza Parade Tour for One, Two, or Four from Second City Tours (Up to 60% Off)

Second City Tours

Near North Side

Guides will lead you through River North to sample pizza from local eateries, including the original Uno Pizzeria & Grill

$50 $23

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Second City Tours: One, Two, or Four Tickets to Belmont Food Binge Tour from Second City Tours (Up to 60% Off

One, Two, or Four Tickets to Belmont Food Binge Tour from Second City Tours (Up to 60% Off

Second City Tours

Lakeview

Enjoy Lakeview’s ethnic- and American-food offerings, including tacos, French pastries, falafel, and grilled cheese

$50 $23

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Brews Cruise Chicago: Brewery Tour in Southwest Chicagoland from Brews Cruise Chicago (Up to  Off). 2 Options Available.

Brewery Tour in Southwest Chicagoland from Brews Cruise Chicago (Up to Off). 2 Options Available.

Brews Cruise Chicago

Chicago

A half-day tour takes you to working breweries where you’ll sample beverages and learn what makes some of your favorite beers so good

$130 $65

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

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

Second City Tours

Water Tower Place

Get your chocolate fix during this tour that visits five of the city’s most beloved sweet-treat havens

$50 $23

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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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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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Illinois River Winery: Tour with Six Tastings and a Glass of Wine or $17 for $30 Worth of Food and Wine at Illinois River Winery

Tour with Six Tastings and a Glass of Wine or $17 for $30 Worth of Food and Wine at Illinois River Winery

Illinois River Winery

North Utica

Sample more than 30 handcrafted wines from the tasting room or sip wines while touring the facility

$30 $17

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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: Loop Architecture Tour for One, Two, or Four from Second City Tours (Up to 61% Off)

Loop Architecture Tour for One, Two, or Four from Second City Tours (Up to 61% Off)

Second City Tours

The Loop

90-minute walking tour takes guests to view some of the city’s most remarkable buildings

$30 $14

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Stray Boots: Interactive Walking Tours of Chicago from Stray Boots (50% Off). Four Options Available.

Interactive Walking Tours of Chicago from Stray Boots (50% Off). Four Options Available.

Stray Boots

 

Clues, trivia, and riddles lead explorers through vibrant neighborhoods via the Stray Boots iPhone or Android app

$24 $12

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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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Kayak Chicago - Chicago River: Architectural Kayak Tour at Kayak Chicago - Chicago River

Architectural Kayak Tour at Kayak Chicago - Chicago River

Kayak Chicago - Chicago River

Chicago

$67.60 $42.10

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

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

O 'Donnell's pub

Mayfair

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

$20 $12

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Wicker Park: Sidewalk Food Tours of Chicago: Wicker Park at Wicker Park

Sidewalk Food Tours of Chicago: Wicker Park at Wicker Park

Wicker Park

Bucktown

$55 $40.50

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Spirit of Chicago: Spirit of Chicago Buffet Cruise at Spirit of Chicago

Spirit of Chicago Buffet Cruise at Spirit of Chicago

Spirit of Chicago

Near North Side

$101.86 $69.87

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Tall Ship Windy of Chicago: 75-Minute Sailing Tour for One Adult with Optional Beverage on Tall Ship Windy (38% Off)

75-Minute Sailing Tour for One Adult with Optional Beverage on Tall Ship Windy (38% Off)

Tall Ship Windy 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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Chicago Helicopter Experience: Daytime Helicopter Tour for Two from Chicago Helicopter Experience

Daytime Helicopter Tour for Two from Chicago Helicopter Experience

Chicago Helicopter Experience

Bridgeport

Passengers soar over the skyline, marveling at the Willis Tower, John Hancock Building, and Trump Tower by day

$256

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Aerial Adventures: Zipline Tour or Full Adventure Package for Two or Four at Aerial Adventures (Up to 51% Off)

Zipline Tour or Full Adventure Package for Two or Four at Aerial Adventures (Up to 51% Off)

Aerial Adventures

Lake Geneva

Adventurers fly on ziplines, climb a tower to experience rappelling and a free-fall jump, and roll in a giant ball down a 300-foot runway

$200 $105

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The Gold Pyramid: $18 for a Tour for Two at The Gold Pyramid ($30 Value). 26 Dates and Times Available.

$18 for a Tour for Two at The Gold Pyramid ($30 Value). 26 Dates and Times Available.

The Gold Pyramid

Wadsworth

Built as a private home in 1977, the 17,000 sq. ft. pyramid features statues, a moat, a three-pyramid garage, and Egyptian-style furnishings

$30 $18

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Margaret Cho: Margaret Cho – The psyCHO Tour on Saturday, October 3, at 8 p.m.

Margaret Cho – The psyCHO Tour on Saturday, October 3, at 8 p.m.

Margaret Cho

The Chicago Theatre

Famed comic and gay icon presents edgy show examining world events and paying tribute to comedy legends Robin Williams and Joan Rivers

$43.57 $29.50

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Select Local Merchants

  • Rotorzen Helicopters
    Rotorzen instills students with the skills and savvy needed to command the open-air cockpit of a powered parachute. Certified instructors nurse knowledge over 60 minutes of pre-flight training, teaching aspiring daredevils how to handle instrumentation and sneak up on cirrus clouds from behind. Students next take to the skies for 30 minutes of turbine-charged cruising as they skim over and sail through the air above the Lansing Municipal Airport. Flight lessons depend upon wind conditions and are offered Friday evenings, Saturday mornings, Saturday evenings, and Sunday mornings. While powered parachutes accommodate only one pilot at a time, individuals can bring along fellow flyers to join in on the acrobatic antics. All flight time can be applied toward FAA sport pilot certification and subsequent opportunities to tickle the moon into sneezing green cheese.
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    6640 South Cicero Avenue
    Bedford Park, 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
  • Chicago Pizza Tours
    Ask an out-of-towner what they want to do when they visit Chicago, and they'll probably tell you they want to chow down on some deep-dish pizza. Chicago Pizza Tours owner and pizza aficionado Jonathan Porter leads parties on treks to some of the Windy City's most celebrated pizzerias with three different pie-themed tours. Guests sample Chicago's signature style with the deep-dish only holiday walking tour, enjoy slices with sides of adult beverages during pizza and cocktails outings, or visit the kitchens of four different restaurants during the original tour. Each outing takes visitors to local favorites across a wide range of styles and cuisines, from the caramelized thick crusts of Pequod's, the stuffed pies of Bacino's, or the Neapolitan-style creations of Spacca Napoli. Recently, Jonathan Porter has teamed up with local writer and tour guide Jonathan Knotek to launch Chicago Prohibition Tours, a romp through some of Chicago's most famous speakeasies still in existence. During the 3.5-hour bus trip through the roaring '20s and beyond, guests can visit the old one-time haunts of gangsters and crooked pols, such as the Green Door Tavern or the Exchequer Restaurant and Pub, all while sipping popular cocktails from almost 100 years ago and communicating only through silent-film title cards.
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    61 East Madison Street
    Chicago, IL US
  • Chicago Detours
    Founder Amanda Scotese, an avid traveler and freelance writer for Rick Steves's renowned travel guides, delegates sure-footed guides to lead sightseers to iconic landmarks and down the back alleys and lesser-known nooks of the Windy City. Tours probe the ins and outs of the Chicago's neighborhoods, such as the Loop, where they fill eyes with the sights of world-renowned architecture and minds with the secrets of the Pedway, an underground walkway that connects buildings throughout the business district with the Ninja Turtles' lair. The Historic Chicago Bar Tour, born of Chicago Detours' desire to spread knowledge of the city's entertainment history, takes tour-goers to three historic bars in an exploration of how the city had fun. Private group Jazz, Blues & Beyond tours explore historic neighborhoods on the North and South sides, and include diversions such as harmonica lessons from a bona fide blues blower. Chicago Detours also offers private-group tours for birthdays, family reunions, and corporate team-building exercises. Private group tour options also include Meat History of Fulton Market and Chicago Neighborhoods and Cultural Diversity.
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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
  • 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

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