Chicago, IL Hotels

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

CHICAGO LOCAL

The Loop

Situated in the centre of Chicago, the tallest building, the ritziest shopping outlets and the most famous cultural institutions make The Loopa 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.

Lakeview

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. TheBriar Street Theatreis a must-visit as it is home to the world-famous Blue Man Group.

Hyde Park

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.

Pilsen

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’.

Lincoln Square

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

CHICAGO EVENTS

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.

GETTING AROUND

· 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.

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