Chicago: what to see, where to stay and how to get around

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On the eighth of October 1871 a fire burned about three and a half square kilometres of Chicago, killed around three hundred people and left a third of the population homeless. The cow that supposedly kicked the lantern was invented by a reporter who later admitted it. What matters is what the city did next: it rebuilt on burnt ground with a new technology, the steel frame, and between 1885 and 1900 a dozen buildings went up here that invented the shape of every city since. This walk is those buildings. Go on a weekday morning, when the lobbies are open and the Loop is working.

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A short history of Chicago

Where the Chicago River flows into Lake Michigan, Jean Baptiste Point du Sable, a trader of African descent, founded the first permanent settlement in the 1780s. In 1837 Chicago received city status, and thanks to the railways and canals it became the trading hub between East and West, with huge slaughterhouses and grain elevators. In 1871 the Great Fire burned much of the city, and during the rebuilding the skyscraper was born here: in 1885 the Home Insurance Building was completed, which is considered the first. In 1893 the city hosted the World's Fair.

The ten best sights in Chicago

1
Art Institute of Chicago
Nighthawks, American Gothic and La Grande Jatte are all in this one building
2
Field Museum
Sue, the most complete Tyrannosaurus ever found, was bought at auction in 1997 for 8.36 million dollars
3
Museum of Science and Industry
In the only surviving building of the 1893 world’s fair; a captured German U-boat is inside it
4
Shedd Aquarium
1930, and the original salt water was shipped in by rail from the Atlantic in twenty tank cars
5
Adler Planetarium
The first planetarium in the western hemisphere, 1930; the skyline view from behind it is the best one
6
Chicago Cultural Center
Free, always; the 1897 Tiffany glass dome inside it is the largest in the world
7
Monadnock Building
The tallest load-bearing masonry building ever built: 66 metres, walls 1.8 metres thick at the base. Verified 10/2026
8
The Rookery
1888, and Frank Lloyd Wright remodelled the light court inside it in 1905; the lobby is open
9
Marquette Building
1895, and the lobby mosaics by Tiffany tell the story of the French explorer the building is named for
10
Reliance Building
1895, and almost entirely glass — the direct ancestor of every glass tower built since

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Tours in Chicago →

A guide in your headphones: open the walk on our site, walk from stop to stop, and at each one your phone tells its story. No guide, no group, and free. This is the first walk in Chicago:

Free walking tours in Chicago

Where the skyscraper was invented

The Rookery · Burnham and Root finished it in 1888 and it is a hybrid — masonry walls on two sides, iron frame on the others — because the technology was changing while it was being built. In 1905 Frank Lloyd Wright, who had worked for the firm, was hired to remodel the glass-roofed light court inside, and he stripped the ironwork and gilded it. The lobby is open in office hours and free, and the spiral stair above it is the thing to look up at.
Monadnock Building · This is the single most instructive building in Chicago, because it is two buildings. The north half of 1891 is load-bearing brick and the walls are a metre and eighty at the base, tapering to forty-five centimetres at the top — at sixty-six metres it is the tallest masonry building ever built, and it is the physical limit of the method. The south half of 1893 is a steel frame with the same floor area and walls a few centimetres thick. Walk from one lobby to the other and the whole argument is in the wall.
Marquette Building · From 1895, and the lobby is a complete Tiffany mosaic cycle telling the story of Jacques Marquette, the Jesuit who came through here in 1674 — including panels of the Native people he met, named, with their own names. The relief panels over the entrance doors are by Edward Kemeys, who also made the Art Institute lions. Entry is free and almost nobody goes in.
Reliance Building · Finished in 1895 and it is almost entirely glass — the brickwork is reduced to thin terracotta strips, because the steel frame carries everything and the wall has no job but to keep the weather out. It is the direct ancestor of every glass tower built since, and it was built in a hurry: the upper twelve floors went up in fifteen days because the whole frame was prefabricated and bolted together.
Sullivan Center · Louis Sullivan designed the rounded corner entrance in 1899 and wrapped it in cast iron ornament of extraordinary density — leaves, stems and interlace, all of it cast in a foundry from his drawings. Sullivan is the man who wrote that form follows function, which is usually quoted to justify plain buildings; he meant that the ornament should grow out of the structure, and this corner is what he actually did about it. He died broke in a hotel room in 1924.
Chicago Cultural Center · Built in 1897 as the city’s first public library, and the money for it came from a book fund raised in Britain after the fire — Queen Victoria, Disraeli and Dickens’s publisher among others sent eight thousand volumes to a city that had just lost its books. The Tiffany dome inside, thirteen metres across and made of thirty thousand pieces of glass, is the largest in the world. Everything here is free and always has been.

The lake the city turned to face

Almost every large lake or river city in the world put industry on its waterfront. Chicago did the opposite, and it was deliberate: an 1836 canal commission marked the lakefront as public ground forever, a merchant named Montgomery Ward sued the city four times between 1890 and 1911 to stop buildings going up on it, and he won. That is why there are twenty-eight kilometres of continuous public shoreline and no private land on it. This walk is the result. Go in the late afternoon; the skyline is lit from the west and the path faces it.

Cloud Gate · Anish Kapoor’s sculpture is a hundred and ten tonnes of stainless steel in a hundred and sixty-eight plates, and the reason it looks like liquid mercury is that every weld seam was ground and polished away by hand after assembly — a process that took far longer than the fabrication. Kapoor objected to the nickname the Bean for years and then gave up. The whole park under it is the roof of a car park and a rail yard.
Crown Fountain · Two fifteen-metre glass block towers with video screens inside them showing the faces of a thousand Chicago residents, filmed by the artist over a year across every neighbourhood. Each face holds still for several minutes and then purses its lips, and a jet of water comes out — a direct joke on the stone gargoyle, which is a water spout with a face. Children stand in the stream all summer and that is the intention.
Lurie Garden · A thousand square metres planted almost entirely with prairie species — the plants that covered Illinois before the plough, two-thirds of them native. The clipped hedge along one side is called the Shoulder Hedge and it refers to the city’s nickname, the City of Big Shoulders, from a 1914 Carl Sandburg poem. The garden sits over an active railway and the soil is only a metre deep.
Buckingham Fountain · Given to the city in 1927 by Kate Buckingham in memory of her brother, and modelled on a fountain at Versailles but built at twice the size. The centre jet reaches forty-six metres and it uses about forty-five thousand litres a minute, recirculated. The four pairs of bronze sea horses represent the four states that touch Lake Michigan.
Adler Planetarium · The first planetarium in the western hemisphere, opened 1930, and the projector was bought in Germany. The reason to come is behind the building rather than inside it: the point of land it stands on gives the single best view of the Chicago skyline, because you are far enough out into the lake to see all of it at once. It is free to stand there and photographers are there at every sunset.
Field Museum · The collection began as the leftovers of the 1893 world’s fair, and it holds Sue, the most complete Tyrannosaurus rex ever found — ninety per cent of the skeleton. Sue was dug up in South Dakota in 1990 and then fought over in court for seven years between the finder, a rancher and the federal government; the museum bought the fossil at auction in 1997 for eight million three hundred and sixty thousand dollars, with help from Disney and McDonald’s.

Pilsen and the South Side

Chicago is one of the most segregated large cities in the United States and that is not an accident of settlement: restrictive covenants on deeds, redlining by banks from the 1930s and a public housing policy that concentrated Black residents in high-rise blocks all did it on purpose, and the pattern is still visible from any elevated train. This route goes into the half of the city that produced the electric blues, gospel music and house music, and into the Mexican quarter that holds the largest Latino cultural institution in the country. Go on a weekday and go in daylight.

National Museum of Mexican Art, Pilsen · Founded in 1982 by two schoolteachers with ten thousand dollars, and it has been free since the day it opened — the only major Latino art museum in the country that has never charged admission, on the stated principle that a community museum cannot ask its community to pay. It is the largest Latino cultural institution in the United States and it is in a park fieldhouse in Pilsen.
18th Street · The neighbourhood is called Pilsen after Plzeň in Bohemia, because Czech immigrants named it in the 1870s, and the ornate brick facades along this street are theirs. It became Mexican from the 1960s when the Taylor Street Italian and Mexican communities were displaced by a new university campus, and the Czech buildings are now covered in Mexican murals. The L station at 18th Street is painted inside and out.
Chess Records, 2120 South Michigan · A two-storey building where Muddy Waters, Howlin’ Wolf, Chuck Berry, Etta James and Bo Diddley all recorded between 1957 and 1967. The Rolling Stones recorded here in 1964 and named an instrumental after the street address. Muddy Waters had arrived in Chicago from Mississippi in 1943 with a suitcase, plugged his guitar in because acoustic could not be heard in a loud bar, and that single practical decision is where rock music comes from.
Pilgrim Baptist Church, Bronzeville · Adler and Sullivan built it in 1890 as a synagogue, and when the Jewish congregation moved north it became a Black Baptist church. Thomas A. Dorsey was its music director from 1932 and he did something new there: he put blues harmony and blues rhythm into sacred music, over furious objection, and invented the genre now called gospel. Mahalia Jackson sang in this building. A fire gutted it in 2006 and the walls still stand.
The site of Chicago Pile-1 · On the second of December 1942, in a disused squash court under the west stands of the university football field, Enrico Fermi and about forty-eight people achieved the first controlled self-sustaining nuclear chain reaction. There was no containment and no shielding; the safety system was a man with an axe standing by a rope. It happened in a residential neighbourhood of a city of three and a half million people. Henry Moore’s bronze marks the spot.
Robie House · Wright finished it in 1910 for a bicycle manufacturer, and it is the clearest statement of the Prairie School: horizontal lines, cantilevered roofs with no visible support, a hidden entrance and no attic or basement in the usual sense. There is also no dining room light fitting — the table has lights built into it. The house was twice scheduled for demolition, in 1941 and 1957, and Wright himself came to protest at the age of ninety.

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Getting to Chicago and getting around

O’Hare International Airport · Twenty-six kilometres north-west; the Blue Line runs to it all night and costs five dollars
Midway International Airport · Fifteen kilometres south-west and much quicker to clear; the Orange Line goes downtown
Union Station · The 1925 Great Hall with its barrel-vaulted skylight is open to walk into and it is free
Clark/Lake · Six of the eight L lines meet here; this is the station to change at, above and below ground
Millennium Station · The Metra Electric line south to Hyde Park and the museums; underground, under the park
Roosevelt · Three lines, and the walk from here to the Field Museum and the aquarium is ten minutes
Chicago Riverwalk · Two kilometres of walkway below street level along the river; the architecture boats leave from it

Cheap eats in Chicago

Chicago food is working food and almost all of it was invented to be eaten standing up or in a car. The city was the slaughterhouse of America — by 1900 the stockyards here killed and packed most of the meat in the country — and the dishes follow from that: beef sliced thin to stretch it, sausage on a bun loaded with vegetables so that it counted as a meal, pizza cut into squares so that it could be eaten with one hand next to a beer. Four to twelve dollars a thing, cards everywhere. One rule that is not a joke: nobody in this city puts ketchup on a hot dog, and asking for it will be remembered.

The Chicago hot dog · Yellow mustard, relish, onion, tomato, pickle, sport peppers, celery salt. No ketchup, ever
Italian beef · Thin-sliced beef in a roll dipped in its own gravy; ask for it wet, hot, and eat it standing
Tavern-style pizza · Thin, cracker-crisp and cut in squares; this is what Chicago actually eats, not deep dish
The jibarito · Steak between two flattened fried plantains instead of bread; created in Humboldt Park in 1996. Verified 10/2026
The Maxwell Street Polish · A grilled Polish sausage with grilled onions and mustard, from the market that invented it
Tacos on 18th Street · Pilsen and Little Village have the city’s best; three dollars, and the carts come out after dark
Chinatown dim sum · Cart service on weekend mornings; point at what passes and pay by the number of plates
Devon Avenue sweets · South Asian sweet shops and chaat by the plate; the street runs two kilometres and nothing is expensive
Argyle Street pho · Vietnamese noodle soup from a community that arrived as refugees from 1975; nine dollars a bowl
Green City Market · Saturday mornings from May in Lincoln Park; growers only, and the chef demonstrations are free

Museums in Chicago

Four of Chicago’s major museums exist because of one event: the World’s Columbian Exposition of 1893, which drew twenty-seven million visits when the entire United States had sixty-three million people, and then left behind its collections, its one surviving building and the ambition that the city should own institutions on that scale. Several of them have free days for Illinois residents and all of them are large enough to need a plan. The Art Institute alone would take two days to see properly.

Art Institute of Chicago · The second largest art museum in the United States; the bronze lions have never had names
Museum of Science and Industry · In the only surviving building of the 1893 fair; a captured German submarine is inside it
Field Museum · Sue the Tyrannosaurus, the Tsavo lions and about forty million specimens, most of them not on show
Shedd Aquarium · 1930; the original sea water came from the Atlantic in twenty railway tank cars, a million gallons
Chicago Cultural Center · Free, always; the thirteen-metre Tiffany dome inside is the largest stained glass dome in the world
National Museum of Mexican Art · Free since it opened in 1982, on principle; the Day of the Dead show each autumn is the main event
DuSable Black History Museum · Founded in a living room in 1961 and the oldest independent museum of Black history in America
Hull House Museum · Free; Jane Addams lived here from 1889 and the whole settlement movement started in this house
Pullman National Historical Park · The 1880 company town twenty kilometres south; the visitor centre is free and the houses are lived in

Holy places in Chicago

Chicago filled up in fifty years with Poles, Irish, Germans, Czechs, Lithuanians, Italians, Greeks, Jews, and then from 1916 with hundreds of thousands of Black Americans leaving the South, and every one of those arrivals built. The result is a city with more large nineteenth-century religious buildings than it has congregations to fill them: a Sullivan synagogue that became a Baptist church and invented gospel, a Polish basilica on a street where nobody speaks Polish any more, and a Hindu temple out past the airport. Most are open and most are free.

Pilgrim Baptist Church · Built by Adler and Sullivan in 1890 as a synagogue; gospel music was invented inside it in the 1930s
Unity Temple, Oak Park · 1908; Wright built it in poured concrete because the congregation had only forty-five thousand dollars
Chicago Water Tower · One of the only structures in the burnt district left standing after 1871; free gallery inside
Haymarket Memorial · The 1886 bombing at a labour rally here is why the first of May is International Workers’ Day
St Stanislaus Kostka · The Polish parish of 1867 that had forty thousand members; the expressway was bent around it
Garden of the Phoenix · Japan’s pavilion from the 1893 fair stood here; it was burned by arson in 1946 and the garden remained
Robie House · A UNESCO World Heritage site since 2019 and twice scheduled for demolition before that
Glessner House · An 1887 fortress-like house by H. H. Richardson; the neighbours thought it looked like a jail

Nature and day trips near Chicago

Chicago has the strangest piece of environmental law in urban America: the entire lakefront is public by right, and it has been defended in court since the 1890s, so a city of two and a half million has twenty-eight kilometres of continuous free shoreline with parks, beaches and a path and no private building on it. Inland the story is different and worth knowing — this was tallgrass prairie, almost all of which is gone, and the restored prairie patches in the parks are deliberate reconstructions of a landscape that was ninety-nine per cent destroyed.

Lakefront Trail · Twenty-eight kilometres unbroken; separated bike and pedestrian lanes since 2018
North Avenue Beach · The city beach with the skyline behind it; lifeguarded in summer and free, like all of them
Promontory Point · A limestone headland in Hyde Park; people swim off the blocks and the city has tried to replace them
Lincoln Park Conservatory · Free, 1895, and open in January, which in this city is the entire point
Garfield Park Conservatory · Free; Jens Jensen designed it in 1908 to look like a Midwestern haystack rather than a palace
The 606 · A 4.3-kilometre park on a disused elevated freight line; it opened in 2015 and it is free
Humboldt Park · A Jensen landscape with a prairie river and a 1907 boathouse; the Puerto Rican festival is here in June
Chicago Botanic Garden · Thirty-two kilometres north and free to enter, though parking is not; twenty-seven gardens on nine islands
Montrose Beach dunes · A protected dune and bird sanctuary inside the city; over three hundred species pass through it

Things to do in Chicago with kids

Chicago is one of the easier American cities with children, for three reasons: the museums are world-class and clustered, the lakefront is public and free, and the L is a toy in its own right — an eight-year-old will ride the elevated loop around downtown as an attraction, and it costs the price of a single fare. The one thing to plan around is the weather: January here is genuinely severe, and the free conservatories and the museum campus are what the city itself does in winter.

Museum of Science and Industry · A full coal mine, a captured submarine and a 1934 streamlined train, all walk-through
Shedd Aquarium · Book a timed entry; the Caribbean reef tank has a diver who talks to the crowd through a microphone
Lincoln Park Zoo · Free, every single day of the year, and one of the last free zoos in the United States
Crown Fountain · Children are meant to stand in the water and it runs from May to October; free and supervised
Maggie Daley Park · A playground designed as a landscape, with a climbing wall and a skating ribbon in winter; free
Navy Pier · The Ferris wheel is a reference to the original, which was built for the 1893 fair a few kilometres south
The elevated Loop ride · Ride the Brown or Pink Line once around the Loop for one fare; it is the cheapest tour in the city
Garfield Park Conservatory · Free, warm, and there is a children’s garden with a two-storey seed slide inside it

Nightlife in Chicago

Chicago invented two musical forms that the rest of the world now dances to, and both happened in rooms you can still stand in. Electric blues came out of the South Side in the 1940s when Mississippi migrants plugged in to be heard over a crowd, and house music came out of a club called the Warehouse around 1980 — the word house is short for it. Last call is two in the morning, four at the weekend for licensed late bars, and the blues clubs put on three sets a night. Cover charges are usually ten to twenty dollars.

Buddy Guy’s Legends · Owned by Buddy Guy himself, who still plays a run of nights here in January most years
Kingston Mines · Two stages that alternate so the music never stops; open until four and the kitchen stays open
The Green Mill · Open since 1907 and Al Capone’s man owned a share; the Sunday poetry slam was invented here in 1986
Second City · Founded 1959; the modern form of improvised comedy was developed in this building
Randolph Street and Fulton Market · The restaurant and bar district of the moment, in converted meat-packing warehouses
Logan Square · The young end of the city; cocktail bars and music rooms around a boulevard and a monument

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Frequently asked questions about Chicago

What is there to see in Chicago?

The top sights in Chicago are Art Institute of Chicago, Field Museum and Museum of Science and Industry. The full list on this page has 10 sights, each with a photo and a short note.

How many days do you need in Chicago?

Three to four days are enough to see the best of Chicago without rushing, including at least one walking tour.

Is there a free walking tour in Chicago?

Yes. sleepntrip has 3 free audio walks in Chicago, with no guide and no group: your phone tells the story at every stop. The first one: Where the skyscraper was invented.

How do you get to Chicago and get around?

The main ways are O’Hare International Airport, Midway International Airport and Union Station. Full details are in the transport section on this page.

Where to stay in Chicago, and for how much?

sleepntrip shows only rooms in Chicago that meet nine conditions: a good location, high guest scores, cleanliness, and a price of up to $80 a night for two. Pick your dates and see what is free.

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