Four days in Chicago: The city that invented the skyscraper and still does it best

Three nights downtown: Millennium Park and the Loop, the Art Institute and the river, the museums on the lakefront, and a last morning on the North Side.

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Length
4 days, 3 nights
Where you stay
Chicago
Places
10 across 4 days
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Chicago is the American city architects tell you to go to. The fire of 1871 cleared the middle of it, the money to rebuild arrived immediately, and what went up on the ashes was the first generation of steel-framed towers anywhere. A century and a half later the results are still standing shoulder to shoulder along the river, and you can read the whole argument about how tall buildings should look by walking six blocks.

It is also, and this catches people out, an easy city. The grid is numbered from a single intersection so an address tells you exactly where it is, eight blocks make a mile, and the elevated trains run in a loop around the centre that gives the downtown its name. Nothing in this trip is more than half an hour from a hotel in the Loop.

Four days covers the museums, the towers and the lakefront with room to sit down. Save one evening for a bar with a band in it, because after the buildings, that is the other thing this city has always been good at.

Highlights

  • The glass ledges on the 103rd floor of the Willis Tower, hanging out over Wacker Drive
  • American Gothic and Nighthawks, in the same building, ten minutes from the trains
  • Standing on the Michigan Avenue bridge over a river that engineers made run backwards
  • SUE, forty feet of Tyrannosaurus, standing in the middle of the Field Museum
  • A free zoo in the middle of a park, which almost no city in the world still has

Where to stay

Chicago, three nights

The city sits on flat ground at the bottom corner of Lake Michigan, which is big enough to have a horizon and a surf, and nature never really intended a city here. It took reversing the flow of a river, raising whole buildings out of the mud and building sewers on an unprecedented scale to make the site work at all, and all of that was done in the first thirty years.

Stay in the Loop or just north of the river. The Loop is where the trains, the theatres and most of this trip are, and it empties out after office hours; the streets north of the river stay busier in the evening and are a ten minute walk from the same places. Either way you will be able to walk to breakfast.

Day by day

Day 1 in Chicago

Millennium Park and the view from 103 floors up

Drop the bags and walk east. Everything on this first afternoon is inside the Loop, and the two things worth doing on the day you arrive are both about looking at the city rather than at anything inside it.

Millennium Park was late, over budget and mocked for years before it opened in 2004, at which point it turned out to be excellent. The reflective sculpture in the middle is the thing everybody photographs, the bandshell behind it is a Frank Gehry and hosts free concerts through the summer, and the whole park is built on a deck over a railway yard, which is a very Chicago solution to a problem.

Then go up. The Willis Tower held the title of tallest building in the world for a quarter of a century and its Skydeck is on the 103rd floor, with glass boxes cantilevered out from the side so you can stand on nothing above Wacker Drive. Go in the last two hours of daylight and watch the lights come on across the flat land to the west.

Dinner afterwards is where the deep dish argument gets settled, and it is a short walk in any direction from the base of the tower.

  1. 16:00

    Millennium Park

    Leisure

    Free, open until eleven, and the best introduction to the city there is. The sculpture, the Gehry bandshell and the two glass towers that spit water at children in summer are all within a few minutes of each other.

  2. 18:00

    The Skydeck

    Architecture

    The 103rd floor, and the glass ledges that stick out over the street. Book a timed ticket: the queue without one runs to an hour in summer. The sunset slots go first.

  3. 20:00

    Deep dish, once

    Eat

    Order it when you sit down, because it takes 45 minutes in the oven and nobody warns you. One between two people is plenty, whatever the menu says.

With more time: If you land early, the Chicago Cultural Center across the road from the park is free, has the largest stained glass Tiffany dome in the world, and takes half an hour.

Day 2 in Chicago

The Art Institute, the river and Michigan Avenue

A short walk today, with one very large building in the middle of it. The Art Institute is at the southern end of Millennium Park, so start there and work north up Michigan Avenue afterwards.

The collection is one of the best in the country and the American and Impressionist rooms are the reason most people come: Grant Wood's American Gothic and Edward Hopper's Nighthawks hang here, along with Seurat's enormous Sunday on La Grande Jatte, which is worth standing in front of at two distances. Set a limit before you go in. Three hours does it if you are selective and does not if you are not.

Come out and walk fifteen minutes north to the river. The bridge at Michigan Avenue is where the city started, and the small museum in the southwest bridge tower explains the thing that makes Chicago's engineering famous: the river used to empty into the lake the city drank from, so in 1900 they reversed it and sent it towards the Mississippi instead.

This is also where to get on a boat. The architecture cruises leave from the docks either side of the bridge, run about ninety minutes, and are the single best way to understand how this city is put together. Book ahead in summer.

Then keep walking north up the Magnificent Mile. The Tribune Tower is on the right at the far end of the bridge, and the fun of it is at eye level: fragments of the Parthenon, the Taj Mahal, the Great Wall and dozens of other famous buildings are set into the stone at street level, each one labelled, collected by correspondents who were told to bring something back.

  1. 10:30

    Art Institute of Chicago

    Culture

    Go early, start upstairs with the Impressionists and the American rooms and come down through the Modern Wing. Timed tickets. If you only have ninety minutes, that upper floor is the ninety minutes.

  2. 13:30

    Lunch on the river

    Eat

    The Riverwalk below street level, on the south bank between State and Franklin, is lined with places with tables on the water and is a much better lunch than anything at street level on Michigan Avenue.

  3. 15:00

    Bridgehouse & Chicago River Museum

    Architecture

    Five floors inside the southwest tower of the bridge, about the river and the machinery that lifts the roadway. Small, cheap and genuinely interesting, and it takes forty minutes. Check the days before you walk over.

  4. 16:00

    Tribune Tower

    Architecture

    Built in 1925 after a competition that produced more famous losing entries than winning ones. Walk slowly along the base and read the labels on the embedded stones, which include a piece of the Berlin Wall and, higher up, a moon rock.

With more time: The Magnificent Mile runs another mile north from here and ends at the Gothic pumping station and its stone tower, one of the few things downtown left standing after the fire of 1871. It is a pleasant walk and an expensive one if you go into the shops.

Day 3 in Chicago

The Museum Campus, on a spit of land in the lake

Three museums sit together on made ground at the south end of the downtown parks, a twenty minute walk or a short bus ride from the Loop, and between them they could absorb three days. Doing all three in one is possible and slightly punishing; two is the honest recommendation, and the third is what the afternoon becomes if the weather turns.

The Field Museum is the big one and the one to start with. SUE, at the top of the main stairs, is the most complete Tyrannosaurus skeleton ever dug up, and the Egyptian galleries include a reconstructed tomb you walk down into. A good part of the collection came straight from the World's Columbian Exposition of 1893, which gives the older halls a distinct nineteenth century flavour.

The Shedd is next door and is a serious aquarium rather than a tank with fish in it. The Oceanarium at the back is the one to make time for, because the far wall is glass and the water in the pool appears to run straight into Lake Michigan behind it.

Then walk out along the causeway to the planetarium, which is the smallest of the three and the oldest in the western hemisphere. Do it late in the day even if you skip the star shows, because the view back at the skyline from that point is the postcard, and it is free to stand there.

  1. 09:30

    Field Museum of Natural History

    Culture

    Start with SUE and the Egyptian tomb and let the rest happen. Two hours is a decent visit. There is a combined ticket covering the campus museums that only saves money if you genuinely do more than one.

  2. 12:30

    Lunch between museums

    Eat

    Both museums have cafeterias and neither is a treat. On a decent day, buy something and eat it on the grass looking back at the towers.

  3. 13:30

    John G. Shedd Aquarium

    Leisure

    Beluga whales, otters and a reef exhibit that puts sharks above your head. Timed entry, and the morning slots go first, so book before you come.

  4. 16:00

    Adler Planetarium

    Culture

    Space rocks, two dome theatres and a scale model of the solar system, at the end of the causeway. Go for the last hour, then walk out to the point behind it for the view of downtown that everybody photographs.

With more time: If two museums is enough, spend the spare afternoon walking north to Buckingham Fountain, which runs on the hour and is lit and set to music in the evenings from May to September.

Day 4 in Chicago

The North Side, and a zoo that costs nothing

The last morning goes north, which is where people actually live. Take the Brown or Red line up and get out around Fullerton; the whole of this is walkable from there and the lakefront path runs alongside it if you want to go back downtown on foot.

Lincoln Park Zoo has been free since 1868 and has stayed free, which is rare enough now to be worth going out of your way for. The grounds are old and shaded, the ape house is the standout, and you can walk in for twenty minutes or stay for two hours without anybody minding.

The park it sits in runs a mile and a half along the lake, with a rowing lagoon, a conservatory and a scattering of statues of people with a connection either to Chicago or to Germany, which was who lived here when it was laid out.

Then the airports: allow an hour to O'Hare on the Blue line, forty minutes to Midway on the Orange, and more of both in the afternoon.

  1. 10:00

    Lincoln Park Zoo

    Leisure

    Free, open every day of the year, and small enough to do properly in an hour and a half. The Great Ape House is the one to walk to first; the farm section at the south end is aimed squarely at children.

  2. 12:00

    Lincoln Park

    Leisure

    A mile and a half of green between the streets and the water, with a rowing lagoon, wide lawns and a Victorian glasshouse at the north end that is free and warm. Walk south along the lakefront path afterwards for the skyline view people fly here for.

  3. 13:30

    An Italian beef, standing up

    Eat

    Ordered wet, dipped in the gravy, eaten leaning forward over the counter. Ask for hot peppers. It is not a tidy lunch and it is not supposed to be.

With more time: With a late flight, the Cubs' ballpark in Wrigleyville is fifteen minutes further north on the Red line, and it runs tours on days without a game. Otherwise the Green Mill in Uptown has had live jazz since Prohibition and starts early enough for one set before a train.

Before you go

Getting in

Two airports. O'Hare is 17 miles northwest and takes almost everything international; Midway is closer and mostly domestic. Both are on the end of a train line into the centre, which is cheaper than a taxi and faster than one at rush hour, and the ride from O'Hare costs a little more than an ordinary fare in the other direction.

Trains from the rest of the country arrive at Union Station, on the west bank of the river and ten minutes' walk from the Loop. Chicago is the hinge of the American rail network, so a great many long-distance routes change here whether you wanted to stop or not.

Getting around

The elevated trains, the L, are the thing to use, and the eight lines are named after colours rather than numbers. Tap a contactless card at the turnstile. Downtown they run on the raised tracks that give the Loop its name, which is worth riding once purely for the view into third-floor offices.

The address system is the best thing about navigating here. Everything is numbered from the corner of State and Madison, a difference of 800 in a street number is a mile, and streets running east to west carry an N or S while those running north to south carry an E or W. Once that clicks you will not need a map downtown.

The weather is not a joke

The wind comes off the lake and down the street canyons, and between December and March it can make an ordinary walk unpleasant in a way the temperature alone does not predict. Come in that season and plan indoor days: the museums here are extraordinary and they are all warm.

May, June, September and early October are the good months. July and August are hot, humid and full of lakefront festivals, which is either the reason to come or the reason to avoid it.

Eating

Deep dish is real, it is a knife-and-fork casserole rather than a pizza, and one is enough for the trip. What locals actually eat more often is the thin, square-cut tavern pizza, and the Italian beef sandwich, which is ordered wet or dry and is not improved by being eaten neatly.

The hot dog is a Chicago institution with rules: yellow mustard, onion, relish, tomato, a pickle spear, sport peppers, celery salt, a poppy seed bun, and no ketchup. Asking for ketchup will get you a look, and possibly a lecture.

What stays with people about Chicago is usually the scale of the thing: a lake with no far shore, a river with skyscrapers growing out of it, a grid running flat to the horizon in three directions.

It is a working city that happens to be beautiful, and it does not go out of its way to tell you so. Give it four days and it will.

Make it your trip

Every stop, day and place here lands in your account as an editable trip. Move the days around, swap a city, add your own bookings and costs, and share it with whoever is coming.

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Common questions

Is four days enough for Chicago?
Yes for a first visit. It covers the Loop, the river, the lakefront museums and one neighbourhood, which is the shape of the city. A fifth day would go to Hyde Park on the South Side, where the university, the Frank Lloyd Wright house and the Museum of Science and Industry are.
Where should I stay?
The Loop or the streets just north of the river. The Loop is central and cheap at weekends because it empties of office workers; north of the river costs more and has somewhere to eat at ten at night. Both are on several train lines.
Which observation deck, and is one enough?
One is enough. The Willis Tower Skydeck is higher and has the glass ledges; the deck on the old Hancock building further north is lower but has the better composition, because the Willis Tower and the whole Loop are in the view. Pick on which building you would rather be looking at.
Is the architecture boat tour worth it?
It is the best ninety minutes in the city and the one thing most worth booking ahead. The river runs through the middle of the downtown with buildings rising straight out of the water on both banks, which is a view you cannot get any other way.
How cold does it actually get?
Cold enough that January visits should be planned around indoor days. The wind off the lake is the problem rather than the temperature, and the fix is the same one locals use: a hat, and the pedestrian tunnels under the Loop.
Is Chicago safe for visitors?
The areas in this plan are busy and well policed. Chicago's reputation comes from violence concentrated in a small number of neighbourhoods well away from anywhere a visitor has reason to go. Ordinary city sense applies, particularly in the Loop late at night when it empties out.