Sign Up

Chicago

Chicago is a city of bold architecture on the shore of a lake as wide as a sea, where Midwestern friendliness makes strangers easy to talk to.

Sign Up
Photo: Jrbarc! / CC BY-SA 4.0, via Wikimedia Commons

Chicago

Chicago is the third-largest city in the United States and probably its most rewarding for anyone interested in architecture. After the Great Fire of 1871 destroyed much of the centre, the city rebuilt itself at record speed and became the birthplace of the skyscraper; today the towers of the Loop rise directly from the banks of the Chicago River, and a boat trip between them is one of the great urban experiences in America. To the east lies Lake Michigan, so large that the horizon looks like the sea, with free public beaches, parks and a long lakefront trail running along almost the entire city. Beyond the centre, Chicago is a patchwork of distinct neighbourhoods, each with its own main street, bars and community, shaped by generations of immigrants from Mexico, Poland, Ireland, Italy and many other places. People here have a reputation for being down to earth, direct and welcoming, and conversations start easily at a bar counter or a baseball game. Summers are warm and full of free festivals; winters are long and genuinely cold, and the city simply moves indoors to its music clubs, theatres and restaurants.

Places to visit

The Chicago River and the Riverwalk

The river runs through the heart of the city, lined on both sides by towers from every period of skyscraper history. Along its main branch, the Riverwalk is a promenade below street level with cafés, wine bars, steps to sit on and kayak rentals. The architecture boat tours that leave from here, especially the one run with the Chicago Architecture Center, are the best introduction to the city: in ninety minutes you learn more about Chicago than in a day of walking. Go in the late afternoon, when the light hits the glass.

Millennium Park and Cloud Gate

The city's living room, built over former rail yards on the edge of the Loop. Its centrepiece is Cloud Gate by Anish Kapoor, a giant polished steel sculpture that everyone calls the Bean, which reflects the skyline and the crowds around it. Nearby, the Crown Fountain shows faces of Chicago residents on two glass towers, and Frank Gehry's Jay Pritzker Pavilion hosts free outdoor concerts on summer evenings, with people picnicking on the great lawn. The Art Institute of Chicago, one of the finest art museums in the country, stands right next door.

The Lakefront and its beaches

Thanks to a decision made over a century ago, most of Chicago's lake shore is public parkland rather than private property. The Lakefront Trail runs for around 29 kilometres beside the water and is shared by cyclists, runners and walkers. North Avenue Beach and Oak Street Beach, a short walk from the skyscrapers, are full of volleyball players, swimmers and sunbathers in summer. Few big cities offer a real beach this close to their financial district.

Wicker Park and Logan Square

North-west of the centre, these neighbourhoods are where many young Chicagoans live and go out. Wicker Park has independent shops, record stores, cafés and bars around the meeting point of Milwaukee, North and Damen avenues. Logan Square, further along the Blue Line, has broad boulevards, a farmers market and a lively bar and restaurant scene. The 606, an elevated former railway line turned into a park and trail, links the area and is a pleasant way to walk or cycle between them.

Pilsen

The historic centre of Chicago's Mexican community, south-west of the Loop, known for the large murals that cover its walls, its bakeries, taquerías and galleries. The National Museum of Mexican Art, with free entry, presents Mexican and Mexican-American art and holds a famous exhibition for the Day of the Dead every autumn. Walk along 18th Street, stop for something sweet at a panadería and look out for the murals in the side streets.

Willis Tower Skydeck and 360 Chicago

For the view from above there are two classic options. The Skydeck on the 103rd floor of Willis Tower, for decades the tallest building in the western hemisphere, has glass boxes that extend out from the facade so you can stand above the street. 360 Chicago, in the former John Hancock Center on Michigan Avenue, looks north over the lake and the beaches, and it has a tilting glass platform called TILT for those with a head for heights. Go at sunset on a clear day.

Where to go out

Blues and jazz clubs

Chicago gave electric blues to the world, and the music still lives here every night. Buddy Guy's Legends in the South Loop and Kingston Mines in Lincoln Park have live bands until late, and the Green Mill in Uptown, open since the early twentieth century, is a dark, atmospheric jazz bar that feels unchanged by time. These are relaxed places where it is normal to talk to the people at your table between sets.

Comedy and theatre

The Second City, founded in 1959, is the improvisational comedy theatre where many of America's best-known comedians began, and it still runs shows every night in Old Town. Beyond it, Chicago has a large theatre scene, from major stages in the Loop to small storefront companies in the neighbourhoods. A comedy show is an easy evening plan for two: you laugh together and have something to talk about afterwards.

Free summer festivals

From June to September there is a festival almost every weekend. The Chicago Blues Festival in June and the Chicago Jazz Festival at the end of summer are free, and the Grant Park Music Festival presents free classical concerts at the Pritzker Pavilion. Every neighbourhood also holds its own street festival with music, food and beer stalls. Lollapalooza, one of the biggest music festivals in the country, fills Grant Park at the beginning of August.

Baseball at Wrigley Field

Home of the Chicago Cubs since 1916, Wrigley Field is one of the oldest ballparks in the major leagues, with ivy on its outfield walls and rooftop seats on the surrounding buildings. A summer afternoon game is as much a social occasion as a sporting one; the bars of Wrigleyville around the stadium fill up before and after, and strangers talk to each other easily. You do not need to understand the rules to enjoy it.

West Loop and Fulton Market

The former meatpacking and warehouse district west of the centre has become the city's most talked-about restaurant area, with Randolph Street and Fulton Market lined with restaurants, cocktail bars, breweries and rooftop terraces. It is busy every evening and makes an easy starting point for a night out, with options at every price level.

Things to do

Take an architecture boat tour

If you do only one organised activity in Chicago, make it this one. The boats travel along the main branch and both forks of the river, while the guide explains how the city invented the skyscraper and how each tower reflects its era. The tours run mainly from spring to autumn; sit on the open upper deck and bring a layer, as the breeze on the water can be cool.

Cycle the Lakefront Trail

Rent a Divvy city bike and follow the path along the lake, north towards Lincoln Park and the beaches or south towards the Museum Campus, where the Field Museum, the Shedd Aquarium and the Adler Planetarium stand on a peninsula with one of the best skyline views in the city. The trail is flat, separated from traffic and lively from early morning until sunset.

Eat the Chicago classics

Deep-dish pizza, baked in a tall pan and eaten with a knife and fork, is the famous one, but locals are just as attached to the Chicago-style hot dog, served with a long list of toppings and never with ketchup, and to the Italian beef sandwich. Add a visit to Chinatown, Greektown or the taquerías of Pilsen and Little Village, and you understand how much of the city's identity comes from its immigrant communities.

Spend a day in Lincoln Park

The city's largest park stretches along the lake north of the centre. It contains Lincoln Park Zoo, which is free, a conservatory full of tropical plants, ponds and paths, and the beaches beside it. The surrounding neighbourhood of the same name has tree-lined streets, cafés and bars, and is an easy place to spend an unplanned afternoon.

Ride the 'L'

Chicago's elevated trains run above the streets of the Loop on steel structures more than a century old, and the circuit they make around the centre gives the district its name. Simply riding the Brown Line around the Loop and north through the neighbourhoods is a cheap, memorable way to see the city from between its buildings.

Great first-date spots

Good to know

Best season

Late May to early October is the best time, when the lakefront, beaches, rooftop bars and free festivals are all in full swing. July and August are hot and sometimes humid, and also the busiest months. September is often the most pleasant, with warm days and fewer visitors. Winter, from December to March, is very cold, with snow and sharp winds from the lake, but the city has excellent museums, theatres and music clubs to spend it in. Spring arrives late and weather can change quickly, so bring layers.

Getting around

The CTA's 'L' trains and buses cover most of the city, and the Blue Line runs around the clock between O'Hare Airport and the centre, taking roughly forty-five minutes. The Orange Line connects Midway Airport to the Loop. Pay with a Ventra card, the Ventra app or a contactless bank card. The centre is compact and easy to walk, Divvy city bikes are everywhere, and water taxis cross the river in the warmer months. Ride-hailing apps are widely used, especially late at night.

Language & meeting people

English is the language, and Spanish is widely spoken as well. Chicagoans are known for being friendly, unpretentious and talkative, and it is normal to chat with the bartender or the people next to you at a game or a concert. Sports, food and which neighbourhood you live in are safe conversation starters. Tipping is expected: around 18 to 20 percent in restaurants and a dollar or two per drink in bars. The legal drinking age is 21, and bars check ID, so carry yours.

Where travelers & expats meet

Young newcomers and internationals tend to live in Wicker Park, Logan Square, Lincoln Park, Lakeview and the West Loop, where the bars, cafés and coworking spaces are. The large university population and the many international companies make the city very mixed. Running clubs on the lakefront, beach volleyball leagues, neighbourhood street festivals, language exchanges and trivia nights in bars are popular ways to meet people, and in summer the lakefront itself is the city's main meeting place.

Frequently asked questions

Is Chicago a good city to visit alone?

Yes. The centre is easy to navigate, public transport is good and people are generally friendly and willing to talk. Shared activities make meeting people easy: an architecture boat tour, a free concert in Millennium Park, a baseball game or an evening in a blues club. As in any large American city, stay aware of your surroundings at night and ask locals which areas to avoid.

How many days do I need in Chicago?

Three to four days cover the Loop, the river and the architecture tour, Millennium Park and the Art Institute, the lakefront and one or two neighbourhoods such as Wicker Park or Pilsen. Add more time to enjoy the summer festivals or a baseball game.

Is Chicago expensive?

It is less expensive than New York or San Francisco, but hotels in the centre and restaurants with tips add up. Many of the best things are free: Millennium Park and its summer concerts, the beaches, the Lakefront Trail, Lincoln Park Zoo and the National Museum of Mexican Art. Public transport is affordable.

What is the weather like in Chicago?

Summers are warm to hot, and winters are long, snowy and very cold, made colder by the wind off the lake. Spring and autumn are short and changeable. Whatever the season, check the forecast and bring layers.

When is Chicago at its most sociable?

From June to early September. The beaches, outdoor concerts, rooftop terraces, baseball games and a street festival in some neighbourhood almost every weekend make summer the season when the whole city is out and easiest to meet.

Is it safe to meet someone from an app in Chicago?

Yes, if you follow the usual sensible rules: meet for the first time in a busy public place, tell a friend where you are going and arrange your own way home. The Riverwalk, Millennium Park, the museums and the busy streets of neighbourhoods like Wicker Park are natural first meeting places. Crime rates vary greatly between neighbourhoods, so stay in well-known, lively areas, especially at night.

Meet someone in Chicago

Sign Up

Other destinations

Pattaya Lisbon Barcelona Phuket Amsterdam Berlin Prague Manila