Our guide to where to stay in Chicago uncovers and reveals the details of the most popular neighbourhoods for visitors to Chicago, offering useful tips and recommendations which we hope will help you match your travel plans to a neighbourhood’s atmosphere. Because the Windy City is a big city! And it's a city with cultural riches as diverse as the tastes of America, from the highest-brow to the lowest. So it’s great if you can stay in a spot with lots around to interest you.
Peterfitzgerald via Wikicommon
Chicago’s steel and glass skyscrapers line a particularly scenic stretch of Lake Michigan, creating a striking commercial hub that dominates the Mid-West’s heartland. But there’s a wealth of culture to appreciate here too: world class art galleries, concert halls and theatres, many of them housed in architectural wonders. Expect art on the streets too, accessible to all. And music, ranging from the orchestras in their elegant concert halls to rock venues and festivals, jazz and blues in bars, and all kinds of dance music. Chicago is also a sports mecca, home to pro teams in many disciplines and passionate supporters for all of them — Chicago’s sports bars can be lots of fun. And there’s plenty of green space, and sandy space, where you can get active yourself. Chicago’s food is another magnet for travellers (the variety is really something), influenced by the multicultural denizens of this deliciously artistic, fun, and forward thinking town.
The neighbourhoods of central Chicago, radiating around the Downtown area, are where you’ll find most of the highlights visitors are here for: the museums and galleries, beaches, parks, skyscrapers and shopping. The North Side has the theatres, bars and clubs; the South Side has beaches, the soul food, Chinatown and some great museums; and the West Side is fashionably gritty. It’s relatively easy to cruise between these areas: the block numbers are constant and public transport is cheap and mostly efficient. You can choose between trains and buses. The trains are most often referred to as the “L”, which comes from the elevated tracks they run on. Central Chicago is very walkable.
The funny sounding name refers to the elevated rail line that loops the busy dead centre of Downtown Chicago. Lake Michigan is to the east and the Chicago River is to the north and west. Within The Loop are the most famous and impressive of Chicago’s skyscrapers, including Sears Tower, Willis Tower and the Chicago Board of Trade, plus some of the city’s most iconic architecture. Within The Loop you’ll also find the theatre district, the Art Institute of Chicago, the Money Museum, Millennium Park — with its incredibly architectural Pritzker Pavilion and Cloud Gate — and a world-class collection of public art that includes sculptures by some of the biggest names in 20th century art. The Loop is a transport hub for all Chicago, all the elevated rail lines converge here. And plenty of buses do too.
Chicago’s best shopping street, the Magnificent Mile, ends on the Chicago River in Near North, and while there are still some quirky stores and big brands, plus the vast Jeweler’s Centre, in The Loop, it’s better to shop across the river. There are plenty of places to eat here, and they’re busiest during the day. The most touristy sites have clusters of cafes and restaurants around them, but they’ll not always be the best places to eat or drink.
The Near North is on the other side of the Chicago River from The Loop, home of the Magnificent Mile, or Michigan Avenue, Chicago’s most glamorous street, known for its elite fashion designers, department stores, global brand boutiques, and high end restaurants, bars and cafes. The Near North has a couple of distinct neighbourhoods: River North, which is known for its art galleries, restaurants, bars and nightclubs; Streeterville, which is between Lake Michigan and the Magnificent Mile; and the Gold Coast, which is where you’ll find some of Chicago’s grand dame hotels, and some of the most expensive residential streets in the city. The Near North is a busy part of town, but not as bustling as The Loop, and it’s possible to escape the buzz entirely by heading down to the river. The Near North’s best known sight is the Water Tower, which is one of the few survivors of the first city of Chicago, the one that burned almost to the ground in 1871. Other highlights include the Museum of Contemporary Art, The Arts Club of Chicago, and the crowded galleries of River North. Navy Pier, with its 50 acres of shops, eateries and attractions, is on the very edge of the Near North.
Navy Pier juts out from the Near North, half a mile into Lake Michigan, providing 50 acres of entertainment and fun, topped by the famous, king-sized, (196ft) ferris wheel. There are restaurants, bars and cafes, an IMAX theatre, carnival-style rides, a huge funhouse maze, boat tours, the Children’s Museum, the Chicago Shakespeare Theatre, parks with fountains and free performance spaces and wonderful views. And you’re close to the other attractions of the Near North and Downtown Chicago.
By ajay_suresh - Fulton Market District, CC BY 2.0
Even if you’re not staying in Chicago’s Near West you should still swing by Little Italy and Greektown for at least one meal in each. If you’re looking for a real eating out treat, the West loop is where you’ll find some of Chicago’s most expensive and glamorous restaurants. And a hip gallery and club scene. The University of Illinois at Chicago has pushed out a lot of this area’s old-a-day charm, including its major street market and Oprah, but the Chicago Bulls still play here at the United Centre (you can admire Michael Jordan’s statue outside), and there’s a smaller new market to replace the old, which is great for flea market shopping and Mexican food.
South Side is a collection of quite different neighbourhoods, but they’re all fairly central, offering literature and architecture, bars and galleries, jazz and history, and green spaces. Hyde Park is for literature and architecture, with Victorian mansions, restored Prairie Schools, and some incredible offerings by Frank Lloyd Wright. It is probably best known for hosting the Chicago World’s Fair, and the Museum of Science and Industry is one of its legacies, but it’s also known for its incredible bookstores (it has more Nobel prizes per square kilometre than any other neighbourhood on the planet). Bridgeport-Chinatown is for the bars and galleries, and of course Chinese food too. It’s also historically home to a large Irish-American population, the White Sox, and reputed to be haunted. Bronzeville is for jazz and history: it’s where Louis Armstrong and Count Basie played at the Sunset Cafe, and there are countless monuments and museums to the neighbourhood’s heyday as a hub of African American culture. The major sights are probably Washington Park with its DuSable Museum of African-American History and the ‘Fountain of Time’ sculpture.
Chicago’s West Side neighbourhoods were founded on beer, and that’s not a comment on people enjoying a brew, this is where the German, Polish, Ukrainians and Czech immigrants set up their breweries, and they did very well, creating comfortable, elegant communities with plenty of cultural variation. It’s all different now, but there’s still a flavour of Europe, and this is one of the best places in Chicago for fussy drinkers of beer and coffee.
Wicker Park is one of Chicago’s coolest neighbourhoods, it looks cool and it sounds cool, but it’s not as cool as it was before everyone knew that it was cool. These days the cool is a bit higher end and more accessible for visitors, but there are still plenty of cool places to drink and appreciate how cool you are. As well as being cool, Wicker Park is also the best connected of all the West Side neighbourhoods, with the Blue ‘L’ line running right through. Pilsen has some hip art galleries and great Mexican food, and Logan Square is elegant and residential.
Lincoln Park is a family-friendly neighbourhood close to miles of beautiful parkland. Lots of families live here, close to the Old Town with its theatres and literary history, and the Lincoln Park Zoo. There’s a well maintained shopping strip, and even a beach on the lakefront. Lincoln Park also has a couple of great museums, and, as you walk towards the Old Town, you’re in amongst a collection of impressive old homes and mansions, the most expensive in Chicago, in an area often referred to as the Gold Coast. Lakeview has the nightlife and Wrigleyville, home of Wrigley Field and the Chicago Cubs, which makes it a fantastic destination for anyone looking for some fun, and great music venues. The North Side neighbourhoods also have their fair share of architecture to interest and impress, and there’s lots of choice when it comes to eating or drinking, especially if you want to eat after midnight.
