10 stops
GPS-guided
4 km
Walking
1 hour 45 minutes
Duration
Free
No tickets
About this tour
Stand beneath the Bean as the skyline reflects in your face, walk the Chicago Riverwalk under towers that invented the skyscraper, cross the Michigan Avenue bridge where the city burned and rebuilt itself taller, explore the Art Institute's lions, and understand why every architect in the world comes to school here.
10 stops on this tour
Millennium Park & Cloud Gate
You're standing underneath one of the most photographed sculptures on earth, and the first thing it does is make you look ridiculous. That's the genius of Cloud Gate — formally known as Cloud Gate, unofficially known as the Bean, universally known as the thing that distorts your face in the middle of downtown Chicago. Walk up close and watch what happens to the skyline. The Willis Tower bends. The Hancock stretches. The entire city warps and folds into a liquid silver surface that seems to melt into itself at the centre.
That centre point, the concave hollow underneath where the reflections converge into an infinite tunnel of distorted faces and fractured architecture, has a name: the omphalos, from the Greek for navel. Anish Kapoor, the British-Indian sculptor who designed this thing, chose the word deliberately. This is the navel of Chicago — the point where the city reflects on itself and finds the image a little absurd, which is exactly right.
Read more...Show less
Kapoor won the commission in 1999 with a design that engineers initially said was impossible. The finished sculpture weighs one hundred and ten tonnes, stands ten metres tall, and is made of one hundred and sixty-eight polished stainless steel plates welded together with such precision that you cannot find a seam. Not one. Run your hand along the surface and you feel nothing but cold, continuous metal. The welding alone took years. The entire process required the invention of new fabrication techniques.
It was completed in 2006 and the city has not been the same since. What Kapoor understood about Chicago — and what every great public artwork in this city understands — is that Chicago has a complicated relationship with its own identity. It's the Second City, always in the shadow of New York, always having to prove something. The Bean is the perfect symbol for that: it reflects the city back to itself, slightly enlarged, slightly distorted, impossibly beautiful, and just a little bit funny.
Behind you is the rest of Millennium Park, which is itself a kind of urban miracle. The entire park sits on top of the old Illinois Central rail yards and a parking garage — you are standing on a deck built over active rail lines, and you cannot feel it at all. The park opened in 2004 and immediately became one of the most visited public spaces in America. Jaume Plensa's Crown Fountain — the two fifty-foot glass towers with faces projected on them that occasionally spit water — is fifty metres to your south. Frank Gehry's Jay Pritzker Pavilion, the crinkled stainless steel band shell with its web of overhead speakers that extends the acoustics across the Great Lawn, is to your east.
The Great Lawn holds free concerts all summer. The Chicago Symphony Orchestra plays here. Jazz festivals fill the weekends in June. In winter, the park floods part of its surface for a skating rink. This is a city that builds parks the way other cities build cathedrals.
From here, we walk south to Michigan Avenue and the Art Institute. The route will take you past the edge of Grant Park — the 'people's front yard' of Chicago — with Lake Michigan visible beyond.
Art Institute of Chicago
The two bronze lions that guard the entrance to the Art Institute have been here since 1894, and Chicagoans treat them like mascots. They get dressed for the holidays — winter hats at Christmas, championship scarves when the Cubs or Bears win, flower garlands when someone is feeling whimsical. The lions are named for two benefactors of the museum, but everyone just calls them the north lion and the south lion, which tells you something about Chicago's relationship with formality.
The Art Institute opened in 1893, built to coincide with the World's Columbian Exposition — the world's fair that remade Chicago's reputation and introduced the White City to a generation of visitors who arrived expecting a meatpacking town and found Paris on the lake. The museum's Beaux-Arts building was designed to be permanent, a statement that Chicago intended to compete with the great cultural institutions of the world. A hundred and thirty years later, it does.
Read more...Show less
Inside, you will find Georges Seurat's 'A Sunday on La Grande Jatte,' which is larger than you expect and more extraordinary up close — two million dots of pure colour that resolve into an entire Parisian afternoon. You will find Grant Wood's 'American Gothic,' which is smaller than you expect — those stern Iowa faces fit on a canvas less than a metre tall. You will find Edward Hopper's 'Nighthawks,' the painting of the late-night diner that captured American loneliness so precisely that every photograph of a diner at night has been trying to equal it ever since.
But the Art Institute is deeper than its famous paintings. The Thorne Miniature Rooms — sixty-eight fully furnished dollhouse-scale rooms, each recreating a historical interior from medieval France to twentieth-century California with obsessive precision at one-to-twelve scale — are genuinely unlike anything in any other museum. They were assembled by Narcissa Thorne in the 1930s, and the level of detail is staggering: working fireplaces, hand-painted wallpaper, furniture made from actual walnut and mahogany, carpets woven to spec. Grown adults stop dead in front of them and cannot explain why.
The Modern Wing, added by Renzo Piano in 2009, doubled the museum's gallery space and gave Chicago architecture another building worth discussing. Piano's flying carpet roof — a suspended, light-diffusing screen that floats above the galleries and catches the northern light — is a lesson in how much a ceiling can do. The Modern Wing houses the contemporary collection and connects via the Nichols Bridgeway pedestrian bridge back to Millennium Park.
The museum also holds one of the world's most important collections of architectural drawings and models. For a city obsessed with buildings, this is fitting. The drawings of Louis Sullivan, Daniel Burnham, and Ludwig Mies van der Rohe sit in the archives here. Chicago doesn't just build architecture — it documents it, studies it, treats it as the primary art form. The Art Institute is the proof.
Allow three hours minimum. Four is better. The building closes at five, but the lions stay outside all night.
Chicago Riverwalk
Stand on the Riverwalk and look at the water. The Chicago River flows west here, away from Lake Michigan, and that direction is not an accident. The river used to flow east, draining into the lake, which was also Chicago's source of drinking water. By the late nineteenth century, the city was so large and its sewage so voluminous that it was poisoning its own water supply. People were dying. So in 1900, in one of the most audacious engineering projects in American history, Chicago reversed the flow of the river.
They dug a twenty-eight-mile canal. They built locks. They changed the direction of a river. The Chicago Sanitary and Ship Canal redirected the river's flow westward into the Illinois waterway system, sending the sewage toward the Mississippi rather than the lake. The city of St. Louis, downstream, sued. They lost. Chicago's engineering pragmatism, as usual, was not interested in apologies.
Read more...Show less
The Riverwalk you're walking on was built in 2016 along the south bank of the river, from Lake Shore Drive to Lake Street — roughly a mile and a half of promenade that drops below street level and puts you at water height. From down here, the scale of the buildings above is different. You see the bridges from underneath. You see how the canyon of skyscrapers closes in on both sides. You see the water itself, flowing backwards, carrying kayaks and tour boats and the occasional piece of river garbage with complete indifference.
The architecture boat tours depart from several points along the Riverwalk, and they are the single best way to understand Chicago's skyline. Chicago is a city that was built to be seen from the river. The facades facing the water were designed as statements — the Wrigley Building's white terra-cotta gleam, Marina City's corn-cob cylinders, the Merchandise Mart's enormous limestone bulk. From river level, you understand why architects come here from all over the world.
Every St. Patrick's Day, the Chicago Plumbers Union dyes the river green. The dye — a vegetable-based compound the formula for which is a closely held secret — turns the entire river a vivid, improbable emerald for several hours. The tradition started in 1962 when a plumber used the dye to trace sewage discharge in the river and someone noticed that it looked spectacular. Now eighty thousand people line the banks to watch. Chicago turns its infrastructure into celebration without missing a beat.
The McCormick Bridgehouse Museum, inside one of the bridge towers on the DuSable Bridge, tells the story of the moveable bridges that cross the river. Chicago has more moveable bridges than any city in the world — thirty-seven of them. On a summer morning, when the bridge tenders draw the bridges up to let tall-masted boats through, the whole downtown stops and watches. The city built itself around this river, reversed it when it became inconvenient, and walks beside it every day.
Willis Tower (Sears Tower)
Here is a test for you. Ask any Chicagoan what this building is called. Every single one of them will say Sears Tower. Not Willis Tower, which is its legal name since 2009 when the Willis Group insurance company purchased the naming rights. Sears Tower. The name that was on this building when it opened in 1973, when it was the tallest building in the world, and which is still the name Chicagoans use and will continue to use until someone pries it from their hands. This is a city that does not accept rebranding of its landmarks.
The building was designed by Skidmore, Owings & Merrill, specifically by the team of architect Bruce Graham and structural engineer Fazlur Rahman Khan. Khan's contribution was the structural idea that made the building possible: the bundled tube system. Instead of a single structural frame trying to resist wind forces on a tower of this height, Khan proposed binding nine separate tube structures of different heights together into a bundle, like a handful of drinking straws. The tubes share wind loads between them, making the structure far more efficient than anything that came before. Every supertall building built since — the Burj Khalifa, the Shanghai Tower, the One World Trade Centre — owes a conceptual debt to what Khan worked out for this building.
Read more...Show less
The tower took three years to build, was completed in 1973, and stood as the tallest building in the world for twenty-five years, until the Petronas Towers in Kuala Lumpur surpassed it in 1998. It still stands at four hundred and forty-three metres to roof — six hundred and fifty metres including antenna — and remains the tallest building in Chicago and the Western Hemisphere.
The Skydeck observation deck is on the hundred and third floor. The glass Ledge boxes — four of them, extending four feet beyond the building face — sit slightly below it. You step out onto glass and look straight down. One thousand, three hundred and fifty-three feet of nothing between your feet and Wacker Drive. The glass is an inch and a half thick and rated for several tonnes of load, but that information becomes completely useless the moment you step out there and see the street below through your shoes. People freeze. People laugh. People grab strangers's arms. The Ledge is one of the most reliable ways to find out which of your friends is secretly afraid of heights.
Chicago still calls it the Sears Tower. You should too.
Chicago Architecture Center
Walk inside the Chicago Architecture Center and stand in front of the model. It occupies the entire ground floor — a scale model of downtown Chicago with every building accurate, every street correct, the river cutting through in its engineered backwards direction. Architects and planners study it. Tour guides use it to orient groups. Children put their faces down to street level and pretend to walk through it. There is nothing else quite like it in any American city.
The centre is the hub of Chicago's architecture tourism industry, which says something important about what kind of city this is. Chicago does not primarily market itself as a food city or a music city or a sports city, though it is all three. It markets itself as an architecture city. The boat tours that depart from here are consistently rated among the best tours in any city in America. The walking tours cover the Loop's blocks in exhaustive detail. The bookshop sells more architectural monographs per square foot than any bookshop in the country.
Read more...Show less
All of this traces back to one morning in October 1871, when the Great Chicago Fire started in a barn on DeKoven Street on the south side. Seventeen thousand structures burned. Three hundred people died. One hundred thousand people were left homeless. The fire burned for two days across three and a half square miles of city, and when it was done, there was almost nothing left.
And then Chicago rebuilt. Not slowly, not cautiously, not with the modest ambition of a city that had learned its lesson. Chicago rebuilt with an aggression that still astonishes. Within two years, the commercial district was largely reconstructed. Within a decade, the city was larger than before. And the architects who came to rebuild — Louis Sullivan and his partner Dankmar Adler, Daniel Burnham and John Wellborn Root, William Le Baron Jenney — were not rebuilding the same city. They were inventing something new.
Sullivan's axiom 'form follows function' became the theoretical foundation of modern architecture. His buildings on the south side of the Loop — the Auditorium Building, the Carson Pirie Scott store, the Gage Building — treated the exterior of a building as an honest expression of its structure, not a Classical disguise draped over a steel frame. Burnham's Reliance Building, completed in 1895, was so far ahead of its time that it looks like it was built in 1965. These architects did not know they were inventing modernism. They thought they were just solving problems. Chicago has always been most revolutionary when it thinks it's just being practical.
Tribune Tower
Look at the base of the building before you look at the top. At street level, embedded in the limestone walls, are small stones with brass plaques identifying them. That one there is a fragment of the Parthenon in Athens. That one is from the Colosseum in Rome. That one is from the Berlin Wall. That one is from the Taj Mahal, from Notre-Dame de Paris, from the Great Wall of China, from Westminster Abbey, from the Great Pyramid at Giza, from the White House, from Fort Sumter. There are one hundred and forty-nine stones from forty-nine countries, collected over decades by Chicago Tribune correspondents who were instructed, when they filed their dispatches from the great sites of the world, to also mail back a piece of the building.
The tower itself was built in 1925, the result of an international architecture competition that the Chicago Tribune organised in 1922 with the explicit brief to design 'the most beautiful and distinctive office building in the world.' Two hundred and sixty entries were submitted from twenty-three countries. The winning design by Raymond Hood and John Mead Howells was a neo-Gothic tower with flying buttresses and an octagonal crown — theatrical, ornate, and backward-looking in the way that 1920s America sometimes was when it got nervous about its own modernity.
Read more...Show less
The second-place entry, from the Finnish architect Eliel Saarinen, was not built. But it was more influential than the winner. Saarinen's modernist tower, with its setback profile and its rejection of historical ornament, showed American architects a direction they had been tentatively moving toward but had not yet committed to. Louis Sullivan, who had spent thirty years arguing for exactly this kind of architecture, saw the Saarinen entry and reportedly wept. The competition entries are displayed at the Art Institute.
The WGN radio studios are visible through the ground-floor windows, which is a Chicago thing — this is a city that puts its media institutions on display. The Tribune moved out of the building in 2018 when it was converted to luxury condominiums. The stones remain. They will likely outlast everything else on this street. The fragment of the Colosseum has already survived two thousand years; it can manage a few more decades on Michigan Avenue.
Now look up. The flying buttresses on the upper floors serve no structural function at all — they are ornament, a Gothic fantasy applied to a steel-frame commercial building. But they give the silhouette its drama, and the silhouette is what people remember.
Chicago Water Tower
Everything around this building burned. On the night of October 8, 1871, the fire that started in DeKoven Street swept north and east across the city, consuming wood-frame houses and commercial buildings with equal efficiency. By the time the fire reached this stretch of Michigan Avenue, it had already destroyed the downtown business district. The pumping station across the street caught fire. The neighbourhood around it was ash.
This tower did not burn. Built in 1869 from blocks of Joliet limestone quarried from the bed of the Illinois River, the tower stood in the middle of the fire and survived. Not because limestone is fireproof — it can crack and spall under sufficient heat — but because the width of the streets around it created enough of a break to keep the worst of the flames from concentrating against the walls. Luck, and stone, and a city that happened to space its streets wide enough.
Read more...Show less
The tower was designed by William W. Boyington in a Gothic Revival castellated style that looks, depending on your mood, either charmingly eccentric or completely out of place. Oscar Wilde, visiting Chicago in 1882 on his North American lecture tour, was characteristically direct: he described it as a 'castellated monstrosity with pepper pots stuck all over it.' Chicago did not change the tower. Chicago does not change things because of what visitors say.
Inside the tower is a standpipe — the original cast-iron pipe that helped regulate water pressure from the pumping station across Michigan Avenue, which drew water from Lake Michigan. The pumping station across the street also survived the fire and still pumps water today. Both buildings are now surrounded by the Magnificent Mile — the stretch of Michigan Avenue north of the river that Chicago built as its twentieth-century answer to Paris's Champs-Elysées, lined with flagship stores and hotels in the architectural language of aspiration.
The Water Tower now houses a small city gallery showing work by Chicago photographers, free to enter. But its primary function today is symbolic. It stands at the heart of the most commercial street in the city as a reminder that everything around it was rebuilt from nothing. Chicago's identity is built on that fact: the city burned down and came back larger, more ambitious, more itself. The Water Tower is the proof that it really happened.
Navy Pier
Walk to the end of the pier and look back at the city. From here, standing one point six kilometres out into Lake Michigan, you understand something that is easy to miss when you're inside the city: Chicago sits on an inland sea. Lake Michigan stretches to the horizon in three directions. The water is so vast that it generates its own weather. On a clear day the eastern shore is invisible. The lake holds ten percent of the world's surface fresh water, and it looks it.
Chicago exists because of this water. The city's position at the southern tip of the lake made it the perfect transit point between the river systems of the east and the Mississippi basin to the west. The Chicago Portage — a short stretch of land between the Chicago River and the Des Plaines River that connected the Great Lakes to the Gulf of Mexico — made this location the most strategically important spot in North America's interior for two centuries of trade. The city that grew here was built on the logic of water.
Read more...Show less
Navy Pier was built in 1916 as a shipping terminal and freight transfer point — a functional piece of port infrastructure jutting into the lake to serve the commercial ships that made Chicago wealthy. During World War Two, the Navy used it as a training facility for pilots and aircrews. After the war, it housed the University of Illinois Chicago campus for several years. By the 1970s it was largely derelict. The city renovated it in 1995 and converted it into an entertainment complex: restaurants, a children's museum, an Imax theatre, a ballroom, and at the east end, a Ferris wheel.
That Ferris wheel is a replica of the original — the one invented by George Washington Gale Ferris Jr. specifically for the 1893 World's Columbian Exposition, held in Chicago. The original wheel was two hundred and sixty-four feet tall, carried thirty-six cars each holding sixty passengers, and rotated over a coal-fired steam engine. It was the engineering marvel of the fair, built as a direct response to the Eiffel Tower's debut at the 1889 Paris Exposition. The original wheel was demolished in 1906. The replica on this pier carries forty cars and stands one hundred and fifty feet tall — smaller, but the idea is the same.
The view from the top of the wheel, on a clear day, is the city laid out in the grid that Daniel Burnham and Edward Bennett planned in 1909 — the great Burnham Plan that made Chicago's parks, its lakefront, its street system. The lakefront shall be forever open, clear, and free to the people. That was Burnham's promise. Standing out here in the lake, looking back at that skyline, it still holds.
The 606 Trail & Wicker Park
You're on an elevated trail built on a railway line that stopped carrying freight in 2001 and started carrying pedestrians in 2015. The 606 — named for the first three digits of every Chicago zip code — runs for four point three kilometres from Bucktown in the east to Humboldt Park in the west, seventeen feet above the street grid, through a changing panorama of Chicago neighbourhood life. You can see into back gardens. You can see the tops of the corner three-flats. You can see the city's density at a scale that the street doesn't give you.
The trail was inspired by New York's High Line, which converted a disused elevated freight railway on Manhattan's west side into a public park in 2009. Chicago's version is less manicured, less curated, more neighbourhood — which is to say, more Chicago. The plantings along the trail are native prairie species. The public art is local. The people using it are the people who live in the blocks below it, walking dogs and running morning miles and sitting on the benches with coffee.
Read more...Show less
Wicker Park, the neighbourhood below you, has been the centre of Chicago's creative life since at least the early 1990s, when cheap rents attracted musicians, artists, and the kind of people who open record shops and zine libraries. The Double Door music venue on Milwaukee Avenue has hosted everyone from Smashing Pumpkins to Prince to the Rolling Stones, though it closed in 2017 after a dispute with the landlord. Myopic Books on Milwaukee is still open — four floors of used books, no particular system, a cat. The neighbourhood has a Polish Triangle at the intersection of Milwaukee, North, and Damen — named for the Polish community that lived here for most of the twentieth century, before the artists arrived, before the tech workers, before the coffee shops that charge nine dollars for a single origin pourover.
Wilco, the Chicago band that made the album 'Yankee Hotel Foxtrot' in a loft in this neighbourhood in 2001, turned the experience of being dropped by their record label and releasing the album free online into one of the defining documents of American independent music. The Marina City towers appear on the album cover. Chicago's music runs from Muddy Waters to Kanye West, from the Chicago blues that electrified the Delta tradition to the house music that was invented in the clubs of the South and West sides in the early 1980s and spread to every dance floor in the world. This neighbourhood is one corner of that story.
Wrigley Field
Wrigley Field was built in 1914 and is the second-oldest Major League Baseball park in the United States, after Fenway Park in Boston. It seats forty-one thousand, six hundred and forty-nine people. The ivy on the outfield walls was planted in 1937 by Bill Veeck, who would go on to become one of baseball's great showmen and who understood that baseball parks need character the way churches need stained glass. The scoreboard in centre field is still operated by hand — a crew of workers inside the structure physically hang the metal number panels to update the score and change the lineup. There are two people in there right now, if a game is on, doing exactly what their predecessors did in 1937.
The Chicago Cubs played in this park for one hundred and eight years without winning a World Series. One hundred and eight. The drought became part of the city's identity, part of the Cubs' identity, part of the relationship between the team and its fans, who kept coming back anyway, year after year, because that is what you do with the Cubs. You love them and they break your heart. Everyone who grew up in Chicago has a story about this.
Read more...Show less
Then on November second, 2016, the Cubs won the World Series in Cleveland, in the tenth inning of Game Seven, and the celebration lasted for days. The streets around Wrigley were so crowded that the police stopped trying to manage them and just let the city exhaust itself. Five million people attended the victory parade. Five million — more than a third of the entire population of Illinois. It was the largest gathering in the history of Chicago, and possibly the most joyful.
The neighbourhood of Wrigleyville exists entirely to watch baseball and drink beer, in that order or simultaneously. The bars on Clark Street open at ten in the morning on game days. The rooftop bleachers on the buildings across Waveland and Sheffield avenues — private operations that charge for seating with a direct sight line into the outfield — have been a feature of the park since at least the 1980s, a Chicago solution to the problem of wanting to watch the game without buying a ticket. The Cubs have spent years trying to block the views with scoreboards and windscreens. The rooftop operators have spent years suing them. It is an ongoing negotiation.
Working-class identity and sport are inseparable in Chicago in a way that New York or Los Angeles never quite managed. The Bears play football in the cold without complaint. The Blackhawks win Stanley Cups and the city parades through blizzards. The Cubs lose for a hundred and eight years and five million people show up when they finally win. The Bean reflects the skyline. The ivy grows on the outfield wall. The scoreboard gets updated by hand. Chicago keeps score the old way, and it always will.
Free
GPS-guided walking tour
No account needed. Walk at your own pace.
Free
10 stops · 4 km