Chicago, IL

Destination Location


Are you ready to experience a city so great, it's the inspiration behind some of the best novels, plays and movies? Whether you call it Chi-town, Windy City or the Second City, Chicago is home to one of the most beautiful skylines in the United States.

Chicago is a city of world-class status and unsurpassed beauty, drawing visitors from around the world. Located on the shores of Lake Michigan in the heart of the Midwest, Chicago has a population of more than 2.7 million people and is the host city to world championship sports teams, an internationally acclaimed symphony orchestra, award-winning theatre and more.

From world famous museums and lakefront parks to diverse neighbourhoods, Chicago offers a wide range of attractions. Start with the Chicago Cultural Center, which offers more than 600 free art programs each year and serves as one of the best places to learn about Chicago's history.

When it comes to architecture, Chicago is the birthplace of the modern building. From historic landmarks to contemporary masterpieces, Chicago boasts unique and innovative designs that continue to influence the architectural world today.

Chicago is also world renowned for its collection of museums. Explore a variety of subjects, including modern art, African American culture, astronomy, natural history and much more. Some museums offer free admission and many others have weekly free days. Visitors bureaus scattered around the city are great resources to help you find the best deals.

No trip to Chicago is complete without experiencing its most recognized cuisine: the deep-dish pizza. It is truly an adventure in cheese and tomato sauce with pizzerias all over the city boasting the best pies in Chicago. If you're looking for something different, Chicago has thousands of restaurants serving a medley of culinary delights to suit every taste, every budget and every mood.

Because no trip to Chicago is complete without a little shopping, head down to the centre of the Loop and you'll soon discover exactly why it's called the Magnificent Mile. Along Michigan Avenue are hundreds of designer retail stores, shops and boutiques presenting some of the best finds from around the world.

No matter how you get around - by foot, bus, bike or boat, on the land, lake or river - you can tour all of Chicago, from its famous landmarks to its world-renowned cultural institutions and attractions. A great destination is waiting to be explored.

Learn more about this great destination by visiting Choose Chicago.

Airport served by: ORD

Destination basics

Summers in Chicago are as hot as a fresh deep-dish pizza. With Chicago being located next to Lake Michigan, the humidity can be high during the summer. If you’re visiting during this time, be sure to pack light clothing but take a raincoat in case you encounter late afternoon showers. In July you’ll see average highs of 29 C and lows of 17 C.

Winter travel to Chicago means packing layers; a good winter coat, mittens and a hat, since the average high is about -1 C and the average low is -10 C in January.

Fall and spring are Chicago’s shortest seasons, bringing moderate temperatures and cooler nights, though it’s a great time to get out and explore the city.

Average monthly temperature and average monthly rainfall diagrams for Chicago, IL

It’s natural to assume that Chicago is called the Windy City because of the often-stiff breezes off Lake Michigan, which are magnified by the so-called tunnel effect of the city’s downtown skyscrapers.

While that’s a credible theory, if you ask a local, you’ll be told that the name was actually coined while Chicago was competing with New York to be host city for the 1893 World’s Columbian Exposition. The city’s proud politicians were known to be somewhat bombastic about Chicago’s superiority, earning references to “that windy city” in the out-of-town press.

As it turned out, that civic pride was well-deserved. The exposition took place just 22 years after the Great Chicago Fire of 1871 and Chicagoans were proud of the rebuilding that had taken place. The 900-hectare area that had been levelled by the blaze was a fresh slate for planners. They created a beautiful, architecturally diverse city where the lakefront was set aside for people. That’s why today you see 41 kilometres of public waterfront, rimmed with buildings that are showcases of architectural style.

And Chicagoans are still fiercely proud of their city and its heritage. Many are reluctant to call the Willis Tower anything but “Sears Tower,” its name from 1973—the year it was completed—until 2009. Similarly, many won’t refer to the former Marshall Field’s store as Macy’s (Marshall Field’s department store had been a Chicago institution since the 1890s; the company was bought by Macy’s in 2005).

The city also has its unique food traditions—think Chicago deep-dish pizza, the Chicago hot dog and Italian beef on a bun—all of which are proudly on display and readily available.

And you can’t go to Chicago without hearing live music, especially jazz and blues. Chicago is a place that elevates the free outdoor concert to an art form. Many Chicagoans will cite outdoor music in a park on a lovely summer day as a favourite pastime—and one they’re eager to share with visitors.

The city’s Midwestern friendliness may take you by surprise; it’s a seriously sophisticated place, with world-class theatre (the only city to boast five regional Tony-Award-winning theatre companies), arts, sports and culture—so the down-to-earth attitude of locals is sometimes unexpected.

Chicagoans are great ambassadors of their city. If you stand on a street corner with a map out, a Chicagoan will come to your aid. It’s just the way it is.

Chicago, "The City that Works", "The City of Big Shoulders," “The Second City,” and most famously “The Windy City” is one of the United State’s most culturally significant capitals. It contains several of the United States' tallest buildings and remains a fascinating window to 20th Century American industry and grandeur. With endlessly clattering elevated trains and street musicians playing around almost every corner, the city is a bustling metropolis of art, culture, music and cuisine.

At first glance, Chicago can be overwhelming. Also known as "The City of Neighborhoods," Chicago comprises more than 75 official neighborhoods. Each neighborhood is distinguished by its own distinct quality and character. 

The Loop 

The Loop takes its name from the elevated "El" train that circles around the city's central core. While the downtown area stretches beyond these boundaries, the real pulse of the city is found in this historic district. The Willis Tower(formerly the Sears Tower), the United States' second-tallest building, is here, as is the Chicago Board of Trade, one of the biggest options and futures trading floors in the world. City government offices are also located in the area, as well as the home offices of several global corporations. 

When it's time for the city that works to relax, the Loop does not disappoint. The city's magnificent Harold Washington Library, the Art Institute of Chicago,Chicago Architecture Foundation and the Chicago Cultural Center are all here. 

Thanks to a thriving theater district, the Loop is growing more and more popular with nearby office workers. The restored Ford Center for the Performing Arts-Oriental Theatre hosts lavish Broadway productions while the iconic Chicago Theatre has several musical concerts. The landmark Auditorium Theatre, considered by some the most beautiful theater in America, hosts musicals, concerts and other performances in the South Loop area. The renowned Goodman Theatre also offers several performances throughout the year.

While technically just outside the Loop's borders, Grant Park is still closely tied to the Loop neighborhood. Hugging Lake Michigan, this park is often referred to as "Chicago's Front Yard." The majestic Buckingham Fountain is here, as is a plush rose garden and the Chicago Symphony Orchestra's outdoor home, the Petrillo Music Shell. The park is immense, with the capacity to hold up to three million people, tested annually by the Taste of Chicago festival. Grant Park also plays host to many free music and arts festivals during the summer, including Jazz Fest, Blues Fest and Gospel Fest.

Near North Side 

Just to the north of the Loop is Chicago's Near North Side neighborhood, a collection of several other smaller districts. 

The city's "Magnificent Mile" ("Mag Mile" to locals) is one of the Near North's most famous boulevards. Stretching along Michigan Avenue from the Chicago River to Oak Street, this shopper’s paradise is home to high-scale chains like Neiman Marcus and Bloomingdale's at the 900 North Michigan Avenue Shops, as well as lavish boutiques scattered throughout the area along with many fine hotels and restaurants.

The John Hancock Center is just down the block from the city's links to its past, the Water Tower and the Chicago Water Works, two of the few buildings that survived the Great Chicago Fire of 1871. Water Tower Place, an upscale indoor shopping mall, offers a wide variety of shopping, dining and entertainment options. You can enjoy RL Restaurant, Ralph Lauren’s hip eatery next to the brand’s largest retail location. Nordstrom, Crate & Barrel and Saks Fifth Avenue can be found a few blocks south on Michigan Avenue. 

Of course, all these upscale shops need equally upscale shoppers, most of whom live in Streeterville or the adjoining Gold Coast neighborhood. Originally named after John Jacob Aster, the area’s present moniker describes  the area's opulence. The neighborhood is the nation's second wealthiest, surpassed only by New York City's Central Park East. 

Just north of the Chicago River and a few blocks west of the Mag Mile is River North, home to an eclectic mix of swanky galleries, trendy cafes and theme restaurants like the Hard Rock Café. The area has the second densest concentration of art galleries in the US, only surpassed by Manhattan.

South Loop 

In stark contrast to the opulent skyscrapers and contemporary nightlife, the South Loop offers a quaint, Old World charm, neighborhood bars and small restaurants. Once home to one of the largest publishing centers in the Midwest, the warehouses left behind have been renovated and taken over by young, affluent professionals in walking distance to their jobs in the Loop. The area's focal point, Dearborn Station, is a stylistic beacon for the neighborhood, the former rail transportation hub's façade lavishly restored to its former glory. 

Beyond Downtown 

Lake Shore Drive, one of the city's major north-south arteries, runs along the picturesque lakefront. While the Drive will take you to many of the city's attractions, this boulevard is destination in itself. The lake view, the bold skyline and even the street's own tree-lined medians offer some of the most breathtaking views in the city. 

Lincoln Park 

Once you pass North Avenue, you enter Lincoln Park, home to some of the city’s most beloved attractions. Tree-lined Fullerton Avenue, with its brownstones converted into condos, gives you a feel for the neighborhood residents. Lincoln Park also surrounds the DePaul University neighborhood. A variety of bars, dance spots and inexpensive restaurants cater to the college and just-out-of-college crowd. 

The park from which the neighborhood takes its name is one of the city's largest and most pastoral. Designed by Frederick Law Olmstead, who also drew up the blueprints for New York's Central Park, Lincoln Park encompasses more than 1,000 acres. It includes the famous Lincoln Park Zoo, the Lincoln Park Conservatory, the Peggy Notebaert Nature Museum, a driving range, dozens of recreational fields and several biking and running paths connecting to lakefront beaches. You'll find many pickup games of soccer and ultimate Frisbee here on warm summer days. 


Heading further north brings you to Lakeview, a neighborhood that serves as a popular nightlife center for both the straight and gay communities. These groups tend to party separately, with the standout exception being Berlin, a late-night dance club where hipsters of every orientation party together. 

Halsted Street between Belmont Avenue and Irving Park Road serves as the headquarters for gay nightlife. The area is not hard to find; just look for the gigantic rainbow-colored pylons that line the streets. For dancing, head to Roscoe's Tavern. Don't miss the Center on Halsted, the city's premier destination for LGBT cultural and recreational activities and wide array of social events throughout the year.

If partying is not your thing, don't despair. The area also contains its fair share of restaurants, from Angelina Ristorante and Yoshi's Cafe to the 24-hour Melrose Restaurant

For nightlife without a specific LGBT focus, head a few blocks west to Wrigleyville, a bar neighborhood that gets its name from the nearby Wrigley Field, home of the Chicago Cubs. The district’s numerous taverns here make for excellent bar-hopping, so stop in the Cubby Bear or The Metro, a bar that features live music and up-and-coming rock bands like the Smashing Pumpkins, who played here before they made it big and returned for their final two shows. 

Diners can select from a variety of tastes in Wrigleyville, including Asian, Cajun, Italian and Mexican. Those who prefer to stick with the bar scene can eat well at Sluggers


For more live music, head farther north, where you'll find the Aragon Ballroom, the Riviera and the prohibition-era jazz bar, Green Mill. Some of the best music in the city be it jazz, rock, and anything in between can be found here. 

Wicker Park/Bucktown 

A hot spot for artists and partiers is the Wicker Park/Bucktown area. Hang out at bars like the Blue Note and Holiday Club or restaurants like Northside Bar & Grill and Beat Kitchen to catch up with the hip crowd and find out about what’s going on in the city’s underground scene.

The South Side 

While Chicago’s South Side has traditionally been a bit more rough and tumble than the rest of the city, there are tons of attractions that North Siders often forget about.

As you cruise south on Lake Shore Drive, admire the Museum Campus where the Shedd AquariumAdler Planetarium and the Field Museum converge. If you have the time, you could easily spend a full day in each museum, but it's also well worth a stop just to enjoy the lake views and watch sailboats go by. 

Just south, you pass Soldier Field, home of the Chicago Bears. After driving past this monumental stadium, you come to sprawling McCormick Place, one of the largest convention centers in North America and home to numerous annual trade shows, like the Chicago Boat, RV & Outdoors Show and the Chicago Auto Show. The space includes more than 2.2 million square feet of exhibition space, Chicago's largest ballroom and the Arie Crown Theater

US Celluar Field, formally known as Comiskey Park (though not the same location as the previous Comiskey Park), home of the Chicago White Sox, lies just west of Lake Shore Drive. This modern stadium features an exploding scoreboard that sets off fireworks along with a Sony Jumbo Screen. 

Further south, the charming Hyde Park neighborhood has retained its quaint, old-world charm. Home to the world-famous University of Chicago, the area boasts interesting restaurants like Salonica and Medici, great used book stores like O'Gara & Wilson's (the oldest used bookstore in the country), and the quaint 57th Street Art Fair. Hyde Park is also home to the gigantic 350,000 square-foot Museum of Science and Industry. This monument to 20th-century technology houses a replica coal mine, a German U-Boat and a Zephyr train and the Smart House: Green & Wired, a futuristic home made with eco-friendly materials. 

After visiting the museum, enjoy a counterpoint to the world’s industrial history with a leisurely stroll through Jackson Park. Like its sister to the North, Lincoln Park, Jackson Park was designed by Frederick Law Olmstead. It features a Japanese garden, a bird sanctuary, a reflection pond and a golf course.

Chicago is a destination that has so much to offer visitors. Come and explore the diversity and variety that is Chicago.

Great food isn't the only thing this city has to offer. From its world-class theaters and museums to its ever-growing music and arts scene, Chicago has staked its claim as the Midwest's entertainment capital.

You cannot talk about art in Chicago without mentioning its architecture, from the modern behemoth that is the Willis Tower to the old Water Tower. Several buildings showcase the Modernist genius of Ludwig Miesvan der Rohe, including the IBM building, the Ralph Metcalf Federal Building, numerous structures on the Illinois Institute of Technology campus, and twin "glass house" apartment buildings on Lake Shore Drive. World-renowned architect Frank Lloyd Wright designed many of the beautiful buildings that make the city and surrounding suburbs unique; learn more about him with a visit to his Home and Studio in Oak Park. While in the suburb, be sure to see Unity Temple, the Unitarian Church that Wright designed.

To gain a thorough understanding of the buildings that surround you, visit the Chicago Architecture Foundation, which offers an array of tours by foot, bus and even water. The River Cruise is highly recommended. Another great place to visit is the Chicago Athenaeum: Museum of Architecture and Design, which offers tours, unique exhibits and a wonderful book and gift store.

The Chicago International Film Festival is one of the country's oldest competitive film festivals—a must-see if you happen to be here in the fall. The Navy Pier Imax Theatre is a nice alternative to the standard movie house fare, offering an exciting, panoramic 3-D viewing experience. The Gene Siskel Film Center at the Art Institute of Chicago presents world cinema in a non-commercial context, and hosts a monthly film series. For classic movies in a classic theater, visit the distinctive Music Box Theatre, which shows old films at weekend matinees and foreign and artsy films in the evening.

Chicago is a blues town, with many great blues houses to choose from. Buddy Guy's Legends, owned by the legendary bluesman himself, is sure to please. Kingston Mines is one of the oldest venues in the city, but still holds its own with low admission prices. For great jazz, try the Green Mill, a former Al Capone-owned speakeasy where the best and hottest still play. Another good bet is the Jazz Showcase, which brings big name acts into town. Grant Park offers Blues and Jazz festivals each year.

Alternatives to the blues and jazz are provided by the Cubby Bear, which features rock-n-roll acts. For more live rock, don't miss the Double Door, the Metro, the Riviera or the Aragon Ballroom. If you've ever wanted to be the performer on stage, then head to the Old Town School of Folk Music, which holds classes as well as public performances.

For the more classical side of Chicago, the Chicago Symphony Orchestra and the Lyric Opera are world renowned.

Museums & Galleries
Chicago has a diverse offering of museums. Depending on your length of stay, you will want to take in several of these gems. The Art Institute of Chicago features French Impressionists, an Oriental Collection and great special exhibits. The Adler Planetarium offers a wide array of hands-on exhibits and information about the universe. The Field Museum of Natural History features Sue, the world's most complete remains of a T-Rex. The Shedd Aquarium, the world's largest indoor aquarium and oceanarium, showcases beluga whales. The mammoth Museum of Science and Industry includes a coal mine, a German U-Boat and a Zephyr, and an old-style steam train, all under one roof.

Art lovers will find plenty of options in this city. An obvious choice is the world-class Art Institute of Chicago, which houses a renowned Impressionist collection. The Museum of Contemporary Art and the Terra Museum of American Art are other good bets.

For a more hands-on arts experience, you will not want to miss the summer's 57th Street Art Fair in Hyde Park on the South Side. It is a delightful way to view and purchase original works by local artists. Finally, don't miss dipping in and out of Chicago's myriad galleries. River North is a good place to start. You'll find Carl Hammer Gallery, Fassbender Gallery, and the Illinois Institute of Art all within a few short blocks of each other.

Increasingly, the Loop has become the place to be for large-scale theater. The Cadillac Palace Theatre joins the ranks of the Ford Center for the Performing Arts-Oriental Theatre, the Auditorium Theatre and the Chicago Theatre for Broadway-style shows. The Goodman Theatre has relocated from the Art Institute to a North Loop site. Some good off-Loop theater options include the Steppenwolf Theater, the Victory Gardens Theater and the Royal George Theatre Center.

Second City has launched many a comedian's career, especially those of Saturday Night Live fame. Seating is cabaret-style, the drinks are good, and the improv ensemble shows are top-notch hilarious. Zanies is a Chicago standout for stand-up comedy, with occasional appearances by established stars. For unique, off-the-wall productions, try the Neo-Futurarium.

Chicago is a marvelous mix of awe-inspiring architecture and stunning lake views, blues houses and jazz clubs, celebrity (Michael Jordan) and infamy (Al Capone). It is home to the Willis Tower, architectural gems by the likes of Frank Lloyd Wright, and "da Bears." With this kind of diversity, it's not surprising that the city's culinary offerings are world class.

There is something to suit everyone's appetite, from the classic Chicago-style pizza at Pizzeria Uno to mouthwatering hot dogs to pound-heavy T-bones. Fine dining establishments are top-of-the-line and plentiful. Many excellent ethnic eateries also flourish here, whether you're in the mood for generous Italian, hands-only Ethiopian, Indian curries or spicy Thai.

Get to know the many charming (and tasty) areas of Chicago:

The Loop
This is the heart of downtown, with its elevated commuter tracks, State Street shopping and architectural landmarks. For a taste of classic German food in a classic Chicago setting, you can't go wrong with the Berghoff. The exquisite Everest is a perfect place for big (and big bucks) occasions. And Cajun/Creole-lovers can try The Original Heaven on Seven for the Chicago version of heaven.

While many night-crawlers will want to venture outside the Loop to truly paint the town red, some bars provides a good setting for an after-dinner drink. A favorite is the legendary Miller's Pub.

Magnificent Mile
After shopping for hours in Michigan Avenue's chic shops, you're sure to feel those taste buds kick in. If you're dressed in the designer duds you just bought, dine at the luxurious Spiaggia (its sister Café is just as popular and a bit less expensive.) The Signature Room on the 95th Floor in the John Hancock Tower offers a meal with a breathtaking view.

Stepping just off the strip will lead you to a range of memorable dining options. Allen's Cafe features seasonal menus in an elegant setting. A popular specialty restaurant just off the Magnificent Mile is Big Bowl, known for its Pan-Asian food.

But what the Magnificent Mile has in high-class shopping and fashionable restaurants, it lacks in nightlife. For a true bar-hopping experience, head to the nearby Rush Street bars in the Gold Coast. One Mag Mile bar to try is the Chicago classic, the Billy Goat Tavern. This subterranean institution features a full bar that will lift your spirits even if you are not in the mood for its signature "cheezeborgers."

River North/Gold Coast
The areas surrounding the Magnificent Mile are home to many innovative restaurants. The River North area, a few blocks west of Michigan Avenue, features several trendy and popular restaurants. An eclectic menu tempts diners at mk, Frontera Grill puts a new twist on Mexican fare, and Coco Pazzo offers Tuscan delights. The area is also home to many of the city's theme restaurants like The Original Rock 'n' Roll McDonald's and Harry Caray's.

The more affluent residents of the Gold Coast, a posh area north of Michigan Avenue, would probably frown at the theme restaurants. They prefer high class, as evidenced by their eateries. Steak lovers should visit Chicago Chop House or the celebrity-favorite, Gibson's. The Pump Room at the Omni Ambassador East Hotel offers a taste of glamor and Chicago tradition. Le Colonial on Rush Street features Vietnamese food with a French influence.

You will also find a popular area for nightlife in the Gold Coast.  Young guns on the prowl can go to meat/meet market bars like Butch McGuire's or Mother's

Lincoln Park, Lakeview/Wrigleyville
This is a fun, vibrant community, famous for its boutiques, restaurants and bars. With so many great options, it is impossible to list them all. For starters, you might try sushi at Sai Café or a taste of Spain at Emilio's Tapas. Theater-goers frequently start their evenings with the Italian fare at Vinci.

North of Diversey Avenue, you will find yourself in the Lakeview neighborhood with its plentiful restaurants. Near Wrigley Field, the original Mia Francesca draws crowds with their classic Italian fare.

If you are in the mood to see live music after dinner, see who's playing at the Elbo Room, which features a mix of jazz, rock and spoken word concerts. Another area institution is Metro Smart Bar, where several local bands like the Smashing Pumpkins started their careers before making it big.

Bars line the streets in these areas. Popular destinations include the Cubby Bear and Murphy's Bleachers in Wrigleyville. In Lincoln Park, Kincade's, Durkin's and Glascott's are among the many favorites. Many in the gay and lesbian community head to places like Roscoe's Tavern for their nights on the town.

Hyde Park
This community is known for its diversity, the University of Chicago campus and the renowned Museum of Science and Industry. The culinary offerings are limited, but it offers some gems. Mellow Yellow is a charming local spot with award-winning chili and rotisserie-chicken. The Sit Down Cafe and Sushi Bar is one-of-a-kind, offering creative sushi rolls alongside mouth-watering pizzas and sandwiches.  And Salonica boasts the area's best brunch in a comfortable diner atmosphere with hints of Mediterranean flavor.

It may not be one of the largest Chinatowns you'll visit, but its restaurants hold their own with many authentic offerings. One perennial favorite is Evergreen. For weekend dim sum, Phoenix is your best bet. 

Wicker Park/Bucktown
Le Bouchon serves up creative French bistro fare. Located just outside the Wicker Park area, Mirai, serves sushi in a trendy metal-and-glass club setting. The funky Violet Hour serves up high-end versions of American classics. For a supper club feel and killer martinis, try Club Lucky

It will not take you long to realize that Wicker Park is no slouch in the nightlife department. Holiday Club and The Note are just a few of the neighborhood favorites.


State: Illinois

Country: United States

Chicago By The Numbers
Population: 2,695,600 (city); 10,001,000 (metropolitan)
Elevation: 578 feet / 176 meters
Average Annual Precipitation: 36 inches / 91 centimeters
Average Annual Snowfall: 37 inches / 94 centimeters
Average January Temperature: 21°F / -6°C
Average July Temperature: 73°F / 23°C

Quick Facts

Electricity: 110 volts, 60Hz, standard two pin plugs

Time Zone: GMT -6 ( GMT -5 daylight saving time ); Central Standard Time ( CST )

Country Dialing Code: 1

Area Code: 312; 773; 872

Did You Know?

Chicago's Windy City nickname has nothing to do with weather. It was coined in 1893 by Charles Dana, the editor of the New York Sun newspaper, in commenting on Chicago's politicians.

The claim that Catherine O'Leary's cow knocked over a lantern in the family barn caused the Great Chicago Fire of 1871 is a myth. Chicago Republican reporter Michael Ahern admitting to fabricating that tale in 1893. Mrs O'Leary, who passed in 1895, spent the rest of her life thinking the fire was her fault.


Chicago is located in Illinois and lies next to Lake Michigan. 

The only heights in Chicago come from its skyscrapers. Stretching along the southwestern shore of Lake Michigan, the city is built on a plain 176 metres above sea level. There may not be much topographical relief, but that’s what makes Chicago such a great city for bicyclists. (Locals like to joke that riding into a strong headwind makes it feel like there are hills.)

The city is home to at least 30 kilometres of bike paths, and cycling is a great way to get around. Rent a bike in Millennium Park and take a ride along the shore of Lake Michigan for some great views of the city skyline and one of Chicago’s landmark summer attractions, Navy Pier, which juts out into the lake and is famously marked by its huge Ferris wheel.

Chicago has the benefit of the lake—which offers recreational activities, cool breezes and stunning views from the skyscrapers that face it—as well as the Chicago River, which snakes through the heart of the city. Sailing, water taxis, boat cruises and abundant beaches along the 41 kilometres of lakefront give this Midwestern city a unique sense of place.

The city is laid out on a well-organized grid, which can really be appreciated by viewing it from above; try looking down from the observation decks of the Willis Tower or the John Hancock building. It also features more than 3,200 hectares of parks, within which are woodlands, lagoons, flower gardens and, of course, gathering places.

Chicago is famous for free, open-air concerts, all summer long. And spending time in the city’s parks—all of which seem to feature great views of either the lake or the iconic skyscrapers—is a must-do for any visitor.

The first non-native to settle in the area now known as Chicago was Jean Baptiste Pointe du Sable, a fugitive slave from San Domingo. By 1779, a small settlement had sprung up around his camp, and du Sable's stake was eventually purchased by another trader, who was bought out by Jonathan Kinzie in 1804. As the settlement grew, the government began to see it as a gateway to the Western frontier and erected Fort Dearborn (now the Michigan Avenue Bridge), where the Chicago River and Lake Michigan kissed. The Native Americans were quite unhappy with this situation and in 1812 massacred most of the soldiers and their families. The fort was rebuilt in 1814 and by 1833 Chicago was a lively frontier town.

The promise of a quick buck drew people, and in 1837 Chicago was officially incorporated as a city. The Illinois and Michigan canal opened in 1848. Rail lines soon followed, and Chicago became the nation's inland shipping hub. With the opening of the Union Stockyards on the western fringe of town, Chicago, as poet Carl Sandburg famously put it, became the "hog butcher to the world."

In the 1850s and 1860s, things could not have looked brighter. In just a few years, Chicago grew from a small frontier town to a booming metropolis on the lake, drawing both Easterners and European immigrants.

The summer of 1871 was a scorcher, and rain was scarce. Catherine O'Leary lived on the city's southwest side, and on the evening of October 8, a small fire began in her barn and started to spread. The cow knocking the lantern over into a pile of hay has become the stuff of legends, but no one really knows what started the blaze that would become known as the Great Chicago Fire.

The fire swept across the Chicago River and burnt the business center of the city to the ground. It continued north, destroying everything in its path all the way to Fullerton Avenue. Firefighters were powerless, but the clouds finally granted Chicago a few precious drops of rain, which started to beat the flames into submission 25 hours after the fire began. Most of the city was in rubble, 100,000 people were homeless, 17,450 buildings were burnt to ash. At the time, losses were estimated at 200 million. Chicago was rebuilt from the ground up, bigger, better and more uniquely American than any other city in the country. Louis Sullivan, Daniel Burnham, John Root and Dankmar Adler, among other renowned architects, joined local builders. "Form followed function" and buildings rose to the sky supported by gridworks of steel. Such masterpieces as the Rookery Building, the Monadnock Building, the Auditorium Theatre Building, and the Marquette Building took shape during this time. To prove its place, a group of politicians and businessmen set out to secure Chicago as the site of the 1893 World's Fair through a blustery campaign of self-promotion. A bitter rivalry ensued between Chicago, St. Louis, Washington D.C. and especially New York. In the New York Sun, editorialist Charles A. Dana warned not to listen "to the nonsensical claims of that windy city. Its people could not build a World's Fair even if they won it." Although proven wrong, Dana did coin Chicago's most common nickname, "The Windy City."

Chicago won the contest and built the fair. Under the guidance of Daniel Hudson Burnham, whose motto was "make no little plans, for they have no magic to stir men's blood," a gleaming city of white was erected in Jackson Park. Today, the Museum of Science and Industry stands as the sole survivor of the fairgrounds.

For years, the Levee District was the seat of the corrupt First Ward, run by two of Chicago's greatest characters, Michael "Hinky Dink" Kenna and John "Bathhouse" Coughlin. Theirs was an empire that consisted of the riches of the Loop and the spoils of vice. For years, they reigned as the "Lords of the Levee," but changing social tides brought their empire to an end.

The late 1890s were a time of social reform, and Chicago was in need of reforming, even though one politician screamed that "Chicago ain't ready for reform yet." Under the leadership of Jane Addams and her settlement house movement begun at The Hull House, the lives of thousands of immigrants were made better. At the same time, former baseball player turned minister Billy Sunday, with the support of the Women's Christian Temperance Union, turned his eyes to the Levee. Increasing public outrage at Hinky Dink's and Bathhouse's shenanigans ended in the breakup of the Levee.

While unions and social workers, with the aid of such writers as Upton Sinclair and Theodore Dreiser, alleviated some of the conditions of the poor, the vice that had been contained in the Levee spread through the city. With no centralized base of control, gangs formed to stake their claims. Chicago was about to enter its bloodiest era, one that still stains the public imagination.

During Prohibition, Al Capone had almost a stranglehold on the liquor supply to the city, and he used any means necessary to keep that control. Prohibition ended in 1933, but the fear and violence did not end. Even though Capone was in jail, "The Outfit" continued to run vice in the city. With the coming of the Great Depression in 1929, things only got worse.

Bright moments emerged in the 1930s, though. In 1933, Chicago once again hosted a World's Fair. Chicago pioneered in the broadcasting industry, and would go on to pioneer in television a decade later. Chicago was also a musical innovator. Jazz had crept into the city from New Orleans, along with the likes of Louis Armstrong, and Chicago put its own spin on the music. Benny Goodman learned to play the clarinet at Hull House and in the 1930s ignited America with his brand of swing.

World War II shook America and Chicago out of the Depression. Chicago was a big player in the manufacture and repair of war ships. Municipal Pier, now Navy Pier, became a temporary Navy base and hundreds of Rosie the Riveters could be seen bustling to work each day. The end of the war brought another boom-time, and Chicago prospered with new building projects. 1968 was a notorious year. The Democrats met in Chicago to nominate their presidential candidate. A large group of protesters assembled near The Congress Plaza Hotel on Michigan Avenue. Fearing a violent uprising, Mayor Richard J. Daley cracked down hard. Film footage of Chicago cops clobbering protesters is still hard to watch. Dissatisfaction set in, and many once proud neighborhoods began to crumble. The 1970s saw a period of great urban decline. Things looked bleak. And then the 1980s hit.

With the upsurge in the economy, building began once more in the Loop, with huge office towers springing up everywhere, joining the ranks of the Willis Tower (formerly the Sears Tower) and the John Hancock Tower. It was the busiest time for building in the Loop since Mies van der Rohe erected his steel and glass buildings 20 years before. An influx of people returned to the city from the suburbs. Neighborhoods that had been in decline, such as Lincoln Park and Lakeview, had new life breathed into them.

Today, Chicago stands as a thriving metropolis, the proud home of millions and a popular destination for travelers.

Chicago is a city made for walking. In fact, it’s been ranked as one of the five most walkable cities in America for several years running by Prevention magazine.

With its flat terrain and easy grid system of streets (Madison Street is the demarcation line between the city’s north and south; State Street divides the east side from the west), Chicago is easy to navigate.

Cabs are abundant in the downtown core, and you can often get around (say, back to your hotel with all your Magnificent Mile shopping bags) for under US$10.

But all those trips add up, so check out the L-trains. There are 144 stations and eight rail lines across the city. Two lines offer 24-hour service: the Blue Line, which connects the Chicago-O’Hare International Airport and downtown, and the Red Line, with service the North and South sides via downtown.

There are water taxis that will zip you up and down the Chicago River for US$3 (one way). They are often the better choice during busy times—and unintentionally include a free scenic tour.

If you want to hop a bus, just know that exact change is required. The fare is US$2.25. Several bus lines run 24 hours. If you plan to move around a lot, consider a Chicago Transit Authority three-day or seven-day pass.

Mention Chicago and you’ll often evoke images of deep-dish pizza, stockyards, Al Capone and Wrigley Field. And indeed, the people of Chicago have great respect for their city’s history.

Modern-day Chicago is a classy urban metropolis where you’ll find plenty of historic buildings and a vibrant arts scene. Live theatre aficionados look no further: from the bright lights of Chicago Broadway and Second City to the thriving small theatres, you’ll find an abundance of live shows in Chicago. On top of that, the sheer number of art, theatre and music schools has fostered a cutting-edge, bohemian vibe among the younger population.

The city has more than a dozen museums and countless art galleries including the Art Institute of Chicago, second only in size to the Metropolitan Museum of Art in New York City.

Chicago’s architecture is remarkable, with a mix of Modernist, Gothic, Art Deco and Chicago School skyscrapers on proud display. Architect Frank Lloyd Wright created his signature Prairie School style here, and many examples of this can be found in the outlying neighbourhoods of the city, particularly Oak Park. No visit to Chicago is complete without a trip up the Willis Tower—the tallest building in North America—a stroll down Navy Pier and some time in Millennium Park.

There are also many indoor facilities worth a visit, particularly for families—the Shedd Aquarium, the Museum of Science and Industry and the Field Museum are standout attractions.
And don’t forget the food. There are certain things that define the city—the Chicago-style hot dog and the aforementioned pizza come to mind. But Chicago today is also a foodie’s paradise, with celebrity chefs anchoring restaurants in top hotels, and new eateries opening regularly.
Chicagoans tend to joke that they do a lot of eating and a lot of walking, a testament to the city’s pedestrian-friendliness. The lakefront features gorgeous walking and cycling trails, interspersed with things to see (public sculptures such as Anish Kapoor’s Cloud Gate in Millennium Park, known locally as “the Bean”), places to eat and free live music.

Summer festivals are a staple of life here, from Taste of Chicago to Lollapalooza, and from the Chicago Blues Festival (the world’s largest free blues festival) to the regular free classical performances in Grant Park and Millennium Park.

Chicago is outdoorsy, sophisticated, very friendly—and, yes, a bit windy at times.

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