From prohibition bars to plush pads, verdant parks to vintage stores, Tamara Hinson explores the many sides to this iconic city.

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Wicker Park

Why go? This hip, creative neighbourhood has several fantastic coffee shops and independent boutiques to its name, offering some of Chicago’s best shopping when it comes to one-off finds. The avenues of North, Division, Milwaukee and Damen have the best shops, offering everything from designer labels to vintage stores. The neighbourhood is also a magnet for foodies, with some of the city’s top chefs setting up shop in the area.

What to do: Start with a visit to the Wormhole Café. It’s a great place to get your bearings, thanks to exceptionally friendly staff and a cosy, quirky interior. There’s a DeLorean (from the Back to the Future films) on display, and menus resemble score screens from eighties video games.

For a preservative-free sugar fix, head to Jeni’s Splendid Ice Creams – we recommend the brambleberry flavour. After some shopping (our favourites include Saint Alfred for trainers and Asrai Garden for beautiful homeware), stop by one of Wicker Park’s cocktail bars. The Violet Hour is a beautiful, prohibition-style night spot and offers unusual concoctions such as Sins of the Father, made with Wild Turkey bourbon, Hellfire bitters and tobacco (sounds weird, but it works).

For something a little different Emporium Arcade Bar, where craft beers are served alongside retro arcade games, or the rather exclusive Up & Up, a rooftop bar on the 13th floor of the Robey hotel with views over the twinkling Chicago skyline.

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River North

Why go? One of Chicago’s busiest areas, this former industrial neighbourhood (also known as RiNo) is incredibly eclectic. When factories started closing in the 1970s, artists and entrepreneurs moved in, and today galleries and boutiques fill the streets. Come night-time, it transforms into one of the city’s liveliest entertainment districts.

What to do: Art fans will love the River North Art District, home to the likes of the Echt Gallery. Satisfy hunger pangs with a visit to Gino’s East, Chicago’s second-oldest pizza chain, featuring signed photos of famous visitors from Obama to Lady Gaga. Walk off your indulgences with a stroll – there are countless architectural treasures here, including 330 N. Wabash building, designed by famed architect Ludwig Mies van der Rohe.

Magnificent Mile 

Why go? This city centre, eight-block stretch – otherwise known as North Michigan Avenue – has over 900 stores, along with 300 restaurants and 60 hotels in the section which passes through the downtown area.

What to do: Shop, to begin with. You’ll find everything from designer stores to the staple names, alongside iconic spots such as the Wrigley Building and the 100-storey 875 North Michigan Avenue (formerly the John Hancock Center). But there’s history, too. At 806 North Michigan Avenue you’ll find the beautiful stone Chicago Water Tower, built in 1869 to house a water pump and one of the few buildings to survive the Great Chicago Fire of 1871. Millennium Park is also worth a wander, with Ashish Kapoor’s modern, coffee bean-shaped Cloud Gate sculpture found here.

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Lakeview

Why go? There’s something for everyone here, whether it’s a night at the theatre or a walk through the lakefront 1,200 Lincoln Park.

What to do: See a show in the Belmont Theater District. One of the most spectacular is the Athenaeum, a former church and Chicago’s oldest continuously operating theatre outside downtown. Make the most of the neighbourhood’s position with a stroll along Lincoln Park’s Lakefront Trail, which meanders past a bird sanctuary and harbour. Lakeview is also where you’ll find colourful Boystown, one of America’s largest LGBTQ communities. North Halsted Street is its main artery and boasts fantastic restaurants and bars, including Oyster Bah, where even the Bloody Mary comes garnished with a shrimp.

Old Town

Why go? Chicago’s Old Town might be a relatively small area but it’s one where most visitors will end up, thanks to its wide-ranging appeal – with restaurants, bars and impressive architecture – and position, close to both the waterfront and downtown. It’s a popular entertainment district, with comedy taking centre stage.

What to do: Check out a performance at Zanies Comedy Club or The Second City comedy club, where John Candy, Tiny Fey, Bill Murray and Steve Carell have all cut their teeth; the improv shows are legendary. Some of Chicago’s best restaurants are also found here, including Two Lights Seafood & Oyster (opposite Second City), where food is served as sharer-sized portions.

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Hyde Park

Why go? To hang out at the favourite haunts of Barack Obama, to start with. The former president has a home in South Side’s Hyde Park. This is one of Chicago’s most charming neighbourhoods – partly due to its role as host to the World’s Columbian Exposition back in 1893, which spurred on the creation of beautiful public gardens and award-winning museums.

What to do: Kick things off with a visit to the Museum of Science and Industry, the largest science museum in the western hemisphere. Then explore the area’s architectural gems, which include the wonderfully gothic University of Chicago, close to Obama’s pad, the DuSable Museum of African American History, and the recently renovated Frederick C Robie House, designed by Frank Lloyd Wright.

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Streeterville

Why go? Think of lakefront Streeterville as Chicago’s family-friendly fun zone – it’s got some of the city’s most iconic atttactions, including the Navy Pier and the Museum of Contemporary Art. It’s easily accessible too – just a short walk from River North and the Magnificent Mile. If the sun’s shining, stop off at Oak Street Beach to feel the sand between your toes.

What to do: No visit to Chicago is complete without a spin on Navy Pier’s famous Ferris wheel. Other reasons to check out the pier include the Chicago Children’s Museum and Chicago Shakespeare Theatre, and there’s a good range of shops and restaurants. For a culture fix, it’s got to be the Chicago Shakespeare Theatre, famous for its modern twists on the bard’s classics. The nearby Museum of Contemporary Art has something for every type of art fan – the permanent collections includes 2,500 artworks, including media installations.


Book it

Gold Medal offers three nights at the four-star Millennium Knickerbocker Chicago from £599 per person, based on two sharing a standard double room, including a Chicago Citypass and flights from Heathrow, and valid for travel from November 4-25.
goldmedal.co.uk


Ask the expert

“The architecture is one of my favourite things about Chicago, whether it’s the  skyscrapers or the stunning private homes. It’s a great alternative to New York for those looking for a city break, and a brilliant jumping-off point for tours and road trips exploring the Great Lakes region.”

Malcolm Davies, product destination manager for Funway Holidays


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Where to stay

Upcoming hotels include the 21c Museum Hotel Chicago – set to open by the end of the year – and the 234-room Reserve, a member of Marriott’s Autograph Collection, due to open in the financial district in late 2020.

Save: Moxy Chicago Downtown
A three-star, boutique-style hotel aimed at millennials (there’s a taco counter and the website boasts about “blazing wifi”). From £125 per night
moxy-hotels.marriott.com/en/hotels/chicago-downtown

Spend: Hotel EMC2
A high-tech (think luggage-delivering robots), luxurious four-star property in the city centre. From around £160 per night.
hotelemc2.com

Splurge: The Langham Chicago
The city’s most luxurious property, inside one of the city’s most recognisable buildings – Mies van der Rohe’s skyscraper. From around £230 per night.
langhamhotels.com/en/the-langham/chicago


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