Chicago goes by a few names: Chi-Town, Second City, the Windy City, the City That Works, the City of the Big Shoulders… The list goes on and on, because Chicago can be many things to many people – visitors and locals alike.
It is the city of the skyscraper, with Chicago’s steely, classical skyline boasting the two tallest buildings in the US, the Willis Tower and the Trump Tower.
It is a city at the heart of African-American culture, as the Civil War brought with it a great African-American migration, and with it the beginnings of blues and jazz. More recently it has been associated with two particularly notable African-Americans – Barack Obama and Oprah Winfrey, arguably the most influential people in the US. (The jury’s still out as to who gets the top spot, but there ain’t a President in history who’s served for 25 years straight!)
With beaches (Oak Street and North Avenue), parks (Midway and Washington Park), sport (the Bulls play basketball at the United Centre and the Bears play American Football at Soldier Field) and theatre (The Playground and recent Steppenwolf), perhaps the best name for Chicago would be the City of Many Faces.
Visit with a purpose or wander aimlessly, but either way Chicago will show you its face. Which one you see depends entirely on you.
Chicago’s Top 10
10. Willis Tower Better known by its old name as the Sears Tower, this is the tallest building in the Western hemisphere. It’s worth visiting for the incredible elevator trip alone (103 floors!)
5. Wrigley Field Home to the Chicago Cubs baseball team, Wrigley Field is one of the oldest stadiums in the US. It’s worth catching a game just to feel the history of the place (and for the world-famous hotdogs).
9. Chicago Botanic Garden Set in 385 acres and comprising 24 individual gardens, it’s perfect for an early morning jog or late-night stroll.
4. Museum of Science and Industry If you’ve brought kids, this museum is full of interactive exhibits and mind blowing displays.
8. Lincoln Park Zoo One of the oldest zoos in the country, there is something for everyone here, including a children’s zoo and paddle boats.
3. Art Institute of Chicago One of the world’s largest and most expansive art collections. Multiple trips are needed to enjoy all it has to offer.
7. Auditorium Theatre A national landmark that provides the best cultural, theatrical and musical entertainment in Chicago.
2. John Hancock Observation Deck: Although only the fourth-tallest building in Chicago, its location on the shore provides the best views of the entire city.
6. Oriental Institute Museum With a confusing moniker, this museum actually houses one of the largest collections of ancient Mediterranean artefacts.
1. Millennium Park Set against the beautiful lakefront, Millennium Park is the most interesting and photographed location in Chicago.
- Union Station – All American railroads ran through this enormous neoclassical train station at one point in time.
- 35 East Wacker Drive – Built in the 1920s, this intricate building once housed a 22-storey car lift.
- Buckingham Fountain – This beautiful monument in Grant Park is one of the largest in the world and where The Amazing Race 6 began.
- Chicago Cultural Center – This beautiful building is the country’s first free municipal cultural centre.
- Old Water Tower – The most well-known building to survive the Great Chicago Fire of 1871 and a Chicago symbol.
Chicago Art & Culture
- The Art Institute of Chicago – One of the most visited museums in Chicago and home to impressionist and modern works of art.
- Museum of Contemporary Art – A place to find a variety of intriguing contemporary exhibits and collections.
- Adler Planetarium – The oldest existing planetarium in the world and host to instruments from days past, space exhibits and three theatres.
- Chicago History Museum – A collection of more than 22 million pieces covering everything from the Great Chicago Fire to the famous Bulls basketball team.
- Chicago Theatre – The place to go for presentations from world-famous artists, bands, orchestras and more.
- John Fluevog Shoes – This is the close-out sanctuary for amazing shoes from this unique designer.
- HoyPoloi Gallery – A high-class Asian store selling artwork, lamps, glassware and other things for the home.
- New Maxwell Street Market – A fun place with hundreds of street vendors out every Sunday with many wonderful treasures.
- Magnificent Mile – Or the “Mag Mile”, known for being among the five top shopping streets worldwide with up-market shops.
- Threadless – Where T-shirt lovers can find many unique and original designs.
Gay & Lesbian Chicago
- Downtown – A bar in the River North area open nightly.
- Crew Bar and Grill – A sports-themed bar in Uptown Chicago that also serves contemporary American food.
- Minibar Ultra Lounge and Cafe – A well-frequented bar and restaurant blasting dance and disco music.
- Berlin – This Boystown bar draws a mixed crowd with dance and disco music and urban-style dancing.
- Atmosphere – A place to find a great beats and ogle go-go guys.
- Lake Michigan – The biggest freshwater lake within the United States, with miles of beaches for swimming or walking.
- Grant Park – A lovely area and host to musical festivals throughout the year.
- Millennium Park - A beautiful place with fun activities for every age.
- Midway Park – Featuring summer gardens and wintertime skating.
- Jackson Park – A place that offers beautiful gardens and a golf course.
- Join in community sport activities in Washington Park, including softball and cricket.
- Catch an American football game at Soldier Field, home of the Chicago Bears team.
- Enjoy a professional basketball game courtesy of the Chicago Bulls at the United Centre.
- The United Centre is also home to the Chicago Blackhawks ice hockey team.
- Watch sailboats race off Navy Pier at the annual Race to Mackinac every July.
Situated in the centre of Chicago, the tallest building, the ritziest shopping outlets and the most famous cultural institutions make The Loop a firm tourist favourite.Grant Park in the middle of the city has been there since Chicago was founded – and the majority of the city’s music and cultural festivals taking part within its leafy grounds. The Loop is a place where you can safely lose hours of time just staring at architecture. Our picks for must-ogle buildings are the Rookery, the Jewellers Building and the Fine Arts Building.
Upper-class homes and entertainment make Lakeview a favourite for the big-spending traveller, while also providing the best of Chicago’s sport and nightlife. Lakeview is home to Chicago’s greatest rock venue, the Metro, which has an uncanny knack of booking bands that are just about to make it big. So if you’re interested in catching a live set from the next big thing, check it out!
Lakeview is also home to Schuba’s and The Vic, if you want good rock and good beer. For those wanting more of a cultural experience, Lakeview provides the best of a Chicago tradition – storefront theatre. The Briar Street Theatre is a must-visit as it is home to the world-famous Blue Man Group.
At the centre of the University of Chicago campus, Hyde Park falls into the African-American district of South Side – home of gumbo and real blues. But what used to be a thriving nightclub scene is now, sadly, largely desolate. However, the Checkerboard Lounge (although newly renovated and relocated) still holds some legendary stories. Next door is one of the finest dining experiences in Chicago, with Park 52 offering intriguing décor and delicate foods. Be sure to check out neighbouring Bronzeville, titled the ‘Black Metropolis’, including historical attractions as the Dusable Museum of African-American History.
Wanna know where the Chicago hipster walking down the street across from you found that vintage jacket? The answer is probably Pilsen, and for those looking for a fashionably dirty experience, this is the place to hang out.
Originally settled by Irish and German immigrants, this end of Chicago is full of culture, including the new National Museum of Mexican Art, which highlights the importance and influence of Mexican art on the US, and Biblioteca Popular del Barrio, which provides access to small-run, often socially left and radical literature.
And if you want to buy that jacket we were talking about… Deliciously Vintage and Knee Deep Vintage are your best options: providing ‘glimpses of the future as seen from the past’.
Lazy and sure of itself, Lincoln Square looms big and bold in Chicago’s cityscape. At its heart lies Giddings Plaza, a place for meeting up and enjoying the sound of buskers. The Albany Park Theatre Project sees experienced local theatre-makers guide young ensemble casts through stories of the neighbourhood, a great place to catch up on the myth and history surrounding Lincoln Square (Al Capone, anyone?).
Unique shopping opportunities also exist within the bounds of Lincoln Square. Laurie’s Planet of Sound provides what some call the best music experience in the city, with experienced staff who are mostly musicians. The Book Cellar offers antique and collectible books, frequent book readings and even a glass of wine if you’re so inclined.
Chicago Eat & Drink
One Sixtyblue This renovated pickle factory is the height of Chicago elegance. The open-plan kitchen allows diners to look on as modern French cuisine is prepared with opulent designs in mind.
Alinea Rated the sixth-best restaurant in the world, Alinea brings an amazing but still accessible take to modern cuisine.
Ann Sather With four branches around the city, Ann Sather offers quintessentially Chicago cuisine. Inspired by Scandinavian and Swedish culinary traditions, the food is, simply put, outstanding.
MK With exceptionally high wooden ceilings and hearty brick, it’s hard to believe that this restaurant is new. Its brand of flavourful new American cuisine is attracting food tourists and locals for its non-pretentious manner.
Duke of Perth The only worthwhile Scottish pub in Chicago. There are no TV screens, no distractions, only the people you came with and the people you might leave with. With over 90 blends of whiskey, this is a place for serious drinkers (not to be confused with problem drinkers).
Hopleaf Bar Equipped with a beer garden and a relaxed vibe, the Hopleaf is the perfect example of a neighbourhood bar done right.
Sheffield’s Beer and Wine Garden A hub for the local literary community, you can catch the odd literary reading at Sheffield’s, and enjoy your beer with some culture.
Green Mill Cocktail Lounge With over a century of drinking under its belt, the Green Mill is generally recognised as the best jazz club in the world. The cocktail list is full of favourites, and if you’re extra nice to the bartender he’ll show you what he’s been working on behind the scenes.
In January, still covered by Christmas snow, the Winter Celebration of Lights ignites the largest greenhouse in the United States with music and intricate lighting displays.
With over 400 local artists demonstrating a range of painting, sculpture and performance art, February’s Around the Coyote Art Festival reveals the cultural underbelly of the Second City.
Attracting the best local and international comedy acts, the Chicago Comedy Festival is situated across five of the city’s largest and most renowned theatres in May.
Situated on the lake front, the Chicago Blues Festival coincides with its Gospel counterpart in June. The musical history of Chicago can be split between the two: according to some, Chicago is the birthplace of both the modern blues and modern gospel movements.
In August, the Chicago Old Town district becomes converted into a Japanese cultural hub. Located in and around the Midwest Buddhist Temple, the Ginzo Festival celebrates both ancient and modern Japanese traditions including displays of cuisine, design and martial arts.
In one of the more interesting Chicago traditions, Carolling to the Animals sees the Lincoln Park Zoo in December converted into a Christmas wonderland with real snow and real animals to keep you and all of your senses company.
When To Go
Summer offers a cavalcade of festivals and outdoor events, showing off the best of Chicago. It also attracts loads of tourists, so may be a bit busy for anyone wishing to take it all in at a slower pace.
Winter and autumn are some of the prettiest times in Chicago. The streets are layered with snow and leaves and you’ll have to rug up to look like a local. Tourists seem to avoid the cold, but if you want to embrace a city without the rush of crowds, head to Chicago for Thanksgiving. It’s empty!
What To Miss
Chicago’s Chinatown is great for a walk through, but food and souvenirs are seriously marked up for tourists. Your best bet is visiting Argyle, another Chinese neighbourhood with the same stores but much more reasonable rates.
Avoid Michigan Avenue. Although located in the middle of Downtown, it offers nothing more than expensive shopping and obnoxious crowds.
Although bus tours offer a massive selection of must-see attractions, you’ll be whizzing past things that need a lot longer to digest and enjoy.
Catch a bus: Chicago is too spread out to explore by foot, so buy a ticket in advance and make use of the extensive bus network. Because the city is so expansive, it’s easy to become confused about where you are. Ask the bus driver if in doubt – they’re usually pretty friendly!
Hire a bike: Rated in the Top 10 Cycling Cities in the US, Chicago’s relative flatness means you’ll be able to zoom from location to location. Unfortunately you won’t be able to shop too much and will have to fight the traffic, but the zooming bit will be fun.
If you’re heading out to the suburbs (why not?), catch the train: easily the quickest and safest option.
America’s “Second City” is no pushover. Brassy and bold Chicago combines a salt-of-the-earth, working-class sensibility with all of the cosmopolitan, erudite allure of a major global city.
With a metro population that hovers near 10 million strong, “The Windy City” on Lake Michigan is the dominant force in the vast American Midwest. Chicago’s humble roots are planted firmly in heavy industry and distribution but while the city is still a vital transportation hub, it now plays a much larger role as a paramount financial and big business capital. Tourism is a lynchpin for the home of Michael Jordan, Oprah Winfrey and Barack Obama, with over 44 million annual visitors to the Illinois city.
The Chicago Board and Trade Building
The Chicago Board and Trade Building, with art deco structural design, is a National Historic Landmark.The Willis Tower
The Willis Tower (former Sears Tower) has been the skyscraper of record in the United States for over three decades. The Skydeck on the 103rd is a popular Chicago tourist attraction.The John Hancock Center
The John Hancock Center tower is another icon in the city, with Lake Michigan as a pictorial backdrop. The observation deck on the 94th floor offers expansive views of metro Chicago.Lincoln Park
With over 30 km² of parkland, Chicago merits the motto of “City in a Garden”. Lakefront harbours, museums, recreation areas, wildlife preserves and lagoons are just several of the green space features in store for visitors. Lincoln Park, with over 20 million annual visitors, is the most popular in the city, with a conservatory, free zoo, nature museum and golf course.The Chicago Cultural Center
The Chicago Cultural Center, a reception hall for foreign leaders, is also a fabulous showcase of contemporary art.The Museum Campus
The Museum Campus is a lakefront park with a trio of world class attractions in the Shedd Aquarium, Adler Planetarium and Field Museum of Natural History.
Music and Nightlife
Chicago has a lively entertainment scene, with myriad concert halls that cater to every taste. Jazz, blues and soul music have notable roots in the city. Classical lovers will enjoy the Chicago Symphony Orchestra and Joffrey Ballet. The city is also home to the Lollapalooza rock and alternative music festival, now held in Grant Park every summer.Sports Scene
Chicago constantly ranks as the best sports city in America, with championship teams in a variety of sports. More importantly however, city fans are among the most faithful and obsessive in North America. From the Cubs and White Sox in baseball, Blackhawks in hockey, Bulls in basketball and Bears in football, pro sports and Chicago go hand in hand.Taste of Chicago
Taste of Chicago is a culinary festival without peer. The annual outdoor event in late June draws upward of 3 million people to a slew of food stalls in Grant Park.
Chicago has a continental climate with four seasons that bring typical extremes in summer and winter.
- Winter (December to March) -5-8°C
- Spring (April to May) 5-21°C
- Summer (June to September) 14-29°C
- Fall (October to November) 1-18°C
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