Tours in Andersonville, Chicago


Best Tours: Cupcake Tour of Chicago with Six Tastings for One, Two, or Four from Best Tours (Up to 70% Off)

Cupcake Tour of Chicago with Six Tastings for One, Two, or Four from Best Tours (Up to 70% 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 $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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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

Chicago

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

$50 $25

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Best Tours (Chicago): Admission for One, Two, or Four to the Chicago Riverwalk Food Tour from Best Tours (Up to 60% Off)

Admission for One, Two, or Four to the Chicago Riverwalk Food Tour from Best Tours (Up to 60% Off)

Best Tours (Chicago)

Chicago

Tours make stops at eateries located along the Chicago Riverwalk and introduce tour-goers to Chicago’s history and famous architecture

$50 $25

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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 (Chicago): Gangster Tour of Chicago for One, Two, or Four from Best Tours (Up to 65% Off)

Gangster Tour of Chicago for One, Two, or Four from Best Tours (Up to 65% Off)

Best Tours (Chicago)

Chicago

Tour-goers take a 90-minute jaunt past iconic landmarks and mob movie filming locations while learning about Chicago’s gangster past

$35 $15

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Best Tours (Chicago): Admission for One, Two, or Four to the Chinatown Food Tour of Chicago from Best Tours (Up to 60% Off)

Admission for One, Two, or Four to the Chinatown Food Tour of Chicago from Best Tours (Up to 60% Off)

Best Tours (Chicago)

Chicago

Tours of Chicago’s Chinatown make stops for dumplings, tea, and fortune and almond cookies

$50 $25

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

Pizza Tour of Chicago for One, Two, or Four from Best Tours (Up to 60% Off)

Best Tours (Chicago)

Chicago

Guest stroll past famous Chicago landmarks on their way to the city’s best pizza joints for samples, demos, and history lessons

$50 $22

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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

Chicago

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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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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Best Tours (Chicago): Admission for One, Two, or Four to the Beer & Bacon Tour of Chicago from Best Tours (Up to 58% Off)

Admission for One, Two, or Four to the Beer & Bacon Tour of Chicago from Best Tours (Up to 58% Off)

Best Tours (Chicago)

Chicago

Visit local eateries to try five seasonal beer and bacon samples

$100 $49

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

Brewery Tour in Southwest Chicagoland from Brews Cruise Chicago (Up to Off). Two 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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Chicago Line Cruises: $62 for a 90-Minute Architectural Boat Tour for Two from Chicago Line Cruises ($84 Value)

$62 for a 90-Minute Architectural Boat Tour for Two from Chicago Line Cruises ($84 Value)

Chicago Line Cruises

Chicago

Award-winning Docents tell the stories behind over 50 “cloud busters” and narrate historical events that influenced the present-day skyline

$84 $62

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Segway Experience of Chicago: $37 for a Two-Hour Segway Tour of Downtown Chicago from Segway Experience of Chicago (Up to $65 Value)

$37 for a Two-Hour Segway Tour of Downtown Chicago from Segway Experience of Chicago (Up to $65 Value)

Segway Experience of Chicago

The Loop

Atop a latest-generation Segway PT, guests coast past Buckingham Fountain and Millennium Park, occasionally pausing for photo ops

$65 $37

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The Barrel Run: Gangster History Tour from The Barrel Run (Up to 40% Off)

Gangster History Tour from The Barrel Run (Up to 40% Off)

The Barrel Run

Near North Side

A bus styled to look like an actual beer barrel sets a party-friendly tone for these educational tours of Chicago’s gangster-filled history

$70 $49

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Chicago Crime Tours: Tour by Bus for Two or Four from Chicago Crime Tours (Up to 38% Off)

Tour by Bus for Two or Four from Chicago Crime Tours (Up to 38% 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 $54

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Seadog Cruises: Lakefront Speedboat Tour, Thrill Ride, or Architectural Tour from Seadog Cruises (Up to 31% Off)

Lakefront Speedboat Tour, Thrill Ride, or Architectural Tour from Seadog Cruises (Up to 31% Off)

Seadog Cruises

Navy Pier

Speedboats zip past famed Chicago landmarks along the lakefront and river; informative narration on city’s history and architecture

$29.07 $20

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Bike and Roll Chicago: Sunset Segway Tour from Millennium Park for One or Two from Bike and Roll Chicago (Up to 50% Off)

Sunset Segway Tour from Millennium Park for One or Two from Bike and Roll Chicago (Up to 50% Off)

Bike and Roll Chicago

Millennium Park

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

$75 $39

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Chicago Hauntings Ghost Tour: Choice of Ghost Bus Tour for One or Two at Chicago Hauntings Ghost Tour (31% Off)

Choice of Ghost Bus Tour for One or Two at Chicago Hauntings Ghost Tour (31% Off)

Chicago Hauntings Ghost Tour

Chicago Hauntings Ghost

Paranormal experts narrate a bus tour; specialty tours explore haunted sites inspired by the city’s gothic past or the notorious H.H. Holmes

$36 $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 58% Off)

90-Minute Brewery Tour for Two, Four, or Six with Tastings, Snacks, and Glasses at Argus Brewery (Up to 58% 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

$60 $25

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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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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 $15

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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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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

Chicago

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: Coffee & Hot Cocoa Crawl for One, Two, or Four from Second City Tours (Up to 60% Off)

Coffee & Hot Cocoa Crawl for One, Two, or Four from Second City Tours (Up to 60% Off)

Second City Tours

Chicago

Tour-goers sample coffees, cocoa, desserts, and pastries at some of River North’s most delicious spots

$50 $23

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Second City Tours: One, Two, Three, Tickets to a Chicago Sweet Treats Tour from Second City Tours (Up to 56% Off)

One, Two, Three, Tickets to a Chicago Sweet Treats Tour from Second City Tours (Up to 56% Off)

Second City Tours

Chicago

Guests sample cupcakes, cake balls, truffles, and gelato and a number of famous Chicago sweets shops on this 90-minute tour

$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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Tall Ship Windy of Chicago: 75-Minute Sailing Tour for One or Two on Tall Ship Windy of Chicago (Up to 27% Off)

75-Minute Sailing Tour for One or Two on Tall Ship Windy of Chicago (Up to 27% 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 $22

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Chicago Running Tours & More: Running Tours of Downtown Chicago from Chicago Running Tours & More (Up to 61% Off)

Running Tours of Downtown Chicago from Chicago Running Tours & More (Up to 61% 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

$64 $25

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Sidewalk Food Tours of Chicago: Three-Hour Walking Food Tour for One or Two from Sidewalk Food Tours of Chicago (Up to 26% Off)

Three-Hour Walking Food Tour for One or Two from Sidewalk Food Tours of Chicago (Up to 26% Off)

Sidewalk Food Tours of Chicago

Multiple Locations

Local guides talk about the architecture and history of River North or Wicker Park while stopping at places such as Xoco and Antique Taco

$55 $42

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Second City Tours: One, Two, or Four Tickets to the Chicago Gangster Tour from Second City Tours (Up to 61% Off)

One, Two, or Four Tickets to the Chicago Gangster Tour from Second City Tours (Up to 61% Off)

Second City Tours

Holy Name Cathedral

Guides recount local legends about Al Capone, Dillenger, and more during a 90-minute gangster tour

$30 $14

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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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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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Rhine Hall Distillery: Tour for Two or Four with Fruit Brandy Flights and Souvenir T-Shirts at Rhine Hall Distillery (Up to 51% Off)

Tour for Two or Four with Fruit Brandy Flights and Souvenir T-Shirts at Rhine Hall Distillery (Up to 51% Off)

Rhine Hall Distillery

West Town

Family-owned distillery follows up group tours with tastings of their renowned fruit brandies; includes souvenir tee for each person

$70 $39

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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: 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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Second City Tours: Winter Whiskey Crawl for One, Two, or Four from Second City Tours (Up to 59% Off)

Winter Whiskey Crawl for One, Two, or Four from Second City Tours (Up to 59% Off)

Second City Tours

Near North Side

Explore River North hotspots and sip blended and malt whiskeys paired with breads, cheeses, and meats

$100 $49

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Chicago Riverwalk: Pedway & Loop Tour at Chicago Riverwalk

Pedway & Loop Tour at Chicago Riverwalk

Chicago Riverwalk

The Loop

$20 $13.75

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

One, Two, or Four Tickets to the Burger & Beer 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 beers paired with specialty burgers

$100 $49

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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

Chicago Lakefront

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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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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Photo Sensei LLC: City Muse Photography Tour for One, Two, or Four from Photo Sensei LLC (Up to 81% Off)

City Muse Photography Tour for One, Two, or Four from Photo Sensei LLC (Up to 81% Off)

Photo Sensei LLC

Millennium Park

During 3–4-hour workshop, students will test out their photo skills while touring the city and learning basic photography concepts

$130 $35

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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 44% Off)

Chicago Pizza Walking Tour for Two or Four from Slice of Chicago Pizza Tours (Up to 44% 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

$100 $60

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The Plant: Sustainable-Food Facility Tour for Two or Four at The Plant (Up to 62% Off)

Sustainable-Food Facility Tour for Two or Four at The Plant (Up to 62% 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

$40 $15

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Second City Tours: Notorious Chicago Crime Walk for One, Two, or Four from Second City Tours (Up to 61% Off)

Notorious Chicago Crime Walk for One, Two, or Four from Second City Tours (Up to 61% Off)

Second City Tours

John Hancock Center

90-minute tour explores the sites and shares the stories and secrets behind Chicago’s most infamous crimes

$30 $14

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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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Select Local Merchants

  • Mena Tours & Travel
    Trust your vacation plans with Mena Tours & Travel in Chicago. You won't be disappointed! Drivers will love the easy parking options just steps away from Mena Tours & Travel. So for all your vacation-planning needs, give Mena Tours & Travel in Chicago a call today!
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    5209 N Clark St
    Chicago, IL US
  • Ibn United Travel Service
    Ibn United Travel Service in Chicago will help book your dreamy vacation today. Parking is accessible and not far from the place. Get ready for the trip of a lifetime when you book your next vacation with Ibn United Travel Service in Chicago.
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    1515 W Foster Ave
    Chicago, IL US
  • Issa Travel Agency
    Avoid the hassle of vacation planning and head to the offices of Issa Travel Agency in Chicago for all of your vacation planning needs. Parking is easily accessible. So if you're looking for the best service and the greatest vacation deals, swing by Issa Travel Agency in Chicago today.
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    5643 N Clark St
    Chicago, IL US
  • All Nation Travel
    Whether you are planning a family vacation or a business trip, All Nation Enterprises in Chicago can do the planning for you. With the many nearby parking options, you won't have to worry about forgetting where you parked. Take your next vacation from ordinary to extraordinary with All Nation Enterprises in Chicago.
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    5701 North Ashland Avenue
    Chicago, IL US
  • Chicago Elevated
    Chicago Elevated, run by effusive improv veteran Margaret Hicks, leads curious charges on eclectic group, private, and custom tours of the city. Jaunts lead natives and tourists alike through the city’s oft-overlooked nooks and crannies as Hicks’s jovial voice narrates every step, shedding light on secret areas and easily overlooked historic sites. Her pedway tour sojourns into Chicago’s tiled subterranean antecity, where retailers, restaurants, and mole people mingle. Tours explore sites of famous disasters, visit the ghostly red-light district that once stretched below what is now Printer’s Row, and gaze at downtown’s ornate architecture from the riverwalk. Stationed in Wrigleyville after college, Hicks accrued the healthy sense of humor and comedic timing that pepper each tour at Second City, iO, and other theaters. Though she attempted a move to New York City, Hicks soon discovered she couldn’t stay away from Chicago’s majestic skyline or the skyscrapers’ subtly receding hairlines. A stint in the Chicago Architecture Foundation’s docent program, as well as acting as a tour guide for six years, arm her with insider’s knowledge that soon transfers to listeners’ brains.
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    4870 North Paulina Street
    Chicago, IL US
  • Stinky Onion Tours
    Walking is one of the best ways to get to know a city. It forces you to move slowly, taking in every weathered brick, intriguing alleyway, and door marked with the sign "Do Not Look At This Door." There's also a good chance it will lead to adventure. At least, that's the belief at the heart of Stinky Onion Tours' walking excursions. With a love of walking rivaled only by local pride––as evidenced by the company's name, a nod to the legendary mistranslation that gave Chicago its name––the company uncovers forgotten moments in Chicago's past through a combination of food and historical fact. Tours include Truckin' Along, which introduces the history of the city's food trucks and makes stops for a bite at several. Hobohemia explores the city's long-ago hobo and bohemian culture, and the Old Town tour winds through the historic venues and restaurants of the neighborhood of the same name.
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    Unknown
    Chicago, IL US

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