With the exception of the architecture boat tour , it might not seem like there are many option to tour the city without some mortifying constituent involved like hopping on a Segway . Not the compositor’s case ! There are infinitely cooler ways to pack in plenty of Chicago history and culture outside the horde of ground-effect machine - similar devices . espouse your inside tourist ( maybe not the fanny mob ) and witness the Windy City by land , water , or sky with these of the essence duty tour .

Chicago Helicopter Experience

Viewing the city from cloud level is unquestionably the ultimate style to gain a new linear perspective on Chicago ’s landmarks . Departing from the outskirts of Bridgeport , the chop takes you on an epical aery tour up the sea-coast of Lake Michigan to Montrose Harbor and back . For 15 minute of arc of airtime and original - recite history , it ’s certainly one of the most expensive method acting of touring the metropolis , but the views are unparalleled – whether you ’re loom in the daytime , golden evenfall hour , or at dark .

Chicago Elevated

Former Second City - performer Margaret Hicks treats hitch participant to off - the - cuff storytelling that guarantees some amusement . You ’ll get a comedy - laced , whirlwind account of Chicago ’s public graphics , computer architecture , and larger - than - living characters who helped shape the city through cheap 90 - minute group tour of the Loop and underground footer burrow system . Binocular tours highlight high - up artistic details that often go unnoticed , and she ’ll custom-make private tour based on specific interests , even if you ’re only into fountain and gargoyles .

Frank Lloyd Wright Tours

Designs of the gramps of modern computer architecture ineluctably guarantee some expert attention . combining tours like theWright Around Chicago Touroffer in - depth , steer experience via double-decker . This one hits up celebrated landmarks in the Frank Lloyd Wright Historic District of Oak Park , such as the architect ’s home and studio apartment and Prairie School masterpiece Unity Temple , plus The Rookery Downtown and Robie House in Hyde Park .

Chicago Architecture Foundation River Cruise

This 90 - minute Chicago River cruise explore three branches of the river and crams in more than 50 architectural wonders along the way . Certified docents aboard the First Lady River Cruises point out all the famous skyscraper from River City north to Goose Island , filling in more narrative details than you ’ll probably be able to call in later . Unimpeded view from the river make it a go - to way to unveil the city ’s history through its breathless background .

Chicago Pizza Tours

Much as we value the river for carving through beautiful cityscape , we might love meat , cheeseflower , and bread a little bit more . Pizza is one of the good direction to see and infer the city , and you could discover it one slice at a time by manner of culturally substantial neighborhood pizzerias . On the Original Chicago Pizza Tour , the aptly refer motorbus , " Dough Force One , " take you beyond Downtown to power through an awesome three - hour foodie adventure – accessing the kitchen of several eating house and taste signature mystifying - sweetheart , thrust , coal - oven , tavern - style , and Neapolitan pies .

History On Tap

What could possibly top pizza and history ? BEER and history . Chicago beer and tavern historiographer and source Liz Garibay connects people to the stories behind taverns through thirst - free tours , talk , and experiences . Since 2002 , she ’s been tap into the city ’s yesteryear through its pubs , try that you’re able to interpret and apprise history from all unlike angles . Pub crawls and neighborhood - based tour of duty , such as " Old Town Taverns , " " Pints & the Past on Devon Avenue , " and " Cubs & Pubs : Wrigleyville Taverns , " walk multitude through Chicago ’s celebrated beer history . She ’s even take the show on the road to other international cities , and collaborated to startChicago ’s first Brewseum .

Urban Kayaks Tours

You ’ll have to actually move your arms at a clean unbendable step to avoid colliding with all the computer architecture river cruise sauceboat , but kayaking through the city can be an awe - inspiring and humbling journey . find the delicate balance of staying afloat while learning about the skyline architecture and urban center history along the Chicago River ’s main arm . The Ultimate Fireworks Outing cap off the 1.5 - hr historic duty tour with a Navy Pier fireworks video display . A Chinatown Guided Paddle Tour departs from a beautifully designed boathouse in Chinatown to explore the river ’s south offshoot .

Weird Chicago Tours

trace , gangsters , enigma , and havoc in the Windy City , minus the tops - cheesy costume and bogus theatrics ? bring down little - known spots around the metropolis to uncover strange panorama of Chicago . You wo n’t find lame tours press fabricated legends and cheapjack research here . The originalDevil & The White City Tourdelves into the history of American serial grampus H.H. Holmes and the World ’s Columbian Exposition in 1893 . Others embark on three - 60 minutes themed junket to haunted places , Red Light District hotspots , 1920s speakeasies , mobster hideout , and criminal offense scene that shaped the city ’s story .

Chicago Greeter Tours

hump a acquaintance who can take you around Ithiel Town is always a solid way to have any city , and Chicago is no elision . But booster are n’t always the most knowledgeable ( unless made - up facts are your thing ) . Getting matched with a friendly , well - informed local to give you the inside scoop on the city for complimentary ( seriously , they work on a no - tipping policy ) might be the smarter ticket . And did we observe the public transit bill is on the Chicago Greeter computer program ?

Bobby’s Bike Hike Chicago Tours

If you ’ve ever admit Lakeshore Dr at Nox , you ’ve probably witness the majesty of the city lights . The City Lights at Night Bike Tour cruises through Downtown to see Millennium Park , the sensible horizon from jaw - dropping vantage points around Museum Campus , and Buckingham Fountain ’s light shows at night . The three - 60 minutes Lakefront Neighborhoods Bike Tour takes you along a seven - mile reaching of the Lakefront Trail and off the tourist - beatnik onto quiet vicinity streets , city parks , and North Side beaches . Food & beer , Southside mobster , and sunset museum & park are also options .

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Helicopter tour of Chicago

Chicago Helicopter Tours|Courtesy of Kamil G Photography

Frank Lloyd Wright-designed house in Chicago

Flickr/Steve Silverman

Pizza at Giordano’s in Chicago

Flickr/Tara Sturm

Kayaking in Chicago

Urban Kayaks

Tourists get directions in Chicago

Courtesy of Choose Chicago/Chicago Greeter