The Windy City: a cultural and culinary paradise

Not ready to wave goodbye to summer? Nor am I.

While half of me is excited at the prospect of unearthing woolly jumpers from the depths of the wardrobe, the other half is being dragged kicking and screaming into a pair of cosy boots that are fit for those sneaky autumnal winds. Before the pumpkin spice aromas well and truly fill the air, I fancy one last trip away – and with Chicago still sitting in the mid to high twenties, there’s no better place.

With direct United Airlines flights from Edinburgh to The Windy City, it has never been easier to reach this incredible hubbub of cosmopolitanism. So why has it taken me so long to pack my bags and head for Sinatra’s Toddlin’ Town, or rather Kanye West’s Chi City? Despite our transatlantic friends voting Chicago their favourite destination within the USA, us Scots are still being lured by the glitz and glamour of NYC’s concrete jungle; but we really don’t know what we’re missing.

Here in Chicago, city slickers brush shoulders with Lake Michigan beach-buffs, and American charm blends seamlessly with international delights. After just under a week in Chicago, one of the friendliest cities I’ve had the pleasure of visiting, it’s hard to view this place as anything other than a cultural and culinary joy.

Chicago is a beautiful blend of city and beach life.

Where to stay

Chicago is known as the City of Neighbourhoods, and for good reason – with nearly 80 of them to choose from, it can be difficult to know where to begin.

Some general advice? If you fancy channelling your inner hipster, Wicker Park has enough artisan coffee shops, indie bars and boutiques to bring a smile to any beard-bearing trendsetter. For a slightly swankier vibe, River North is brimming with bougie bars and restaurants, and is a stone’s throw from the heart of the city.

For sports fanatics, Wrigleyville also has much to offer. Though it is slightly further out of town, it is home to the Chicago Cubs’ grounds, Wrigley Field, so sports bars can be found on every street corner, as well as a few ‘sluggin’ joints in which to explore your hidden baseball talents. What’s more, amateurs like me need not worry about the ‘bat at your own risk’ signs – though it might feel like stepping into a cage for battle, plenty of locals will be keen to show you the ropes and holler a few words of encouragement through the nets.

Make sure to take a trip to Wrigley Field to cheer on the Cubs.

We stayed in Hotel Zachary which is based on N Clark St and sits just opposite Wrigley Field. Serving as a peaceful base to escape to after a busy day venturing through the city, I cannot recommend this place highly enough. The staff were welcoming, the food was delicious, and I left each morning feeling I’d had a very comfortable, refreshing night’s sleep. The interiors will also appeal to the baseball fans, with plenty nods to the city’s home sport, as they are inspired by Zachary Taylor Davis, the legendary architect behind Wrigley Field.

Hotel Zachary’s interiors are inspired by Wrigley Field’s architect, Zachary Taylor Davis.

As tempting as it may be to hail a cab in such an expansive city, don’t forget about the ‘L’ – the overground metro – which is an easy way of travelling from A to B, and helps save a few pennies for a cocktail or two in town.

Live like a local

Aside from trying your hand at sluggin’, touring Wrigley Field has to feature on the to-do list – and if you’re fully committed to the cause, so does buying the famous foam finger. Built in 1914, the stadium has witnessed some of the most remarkable baseball games in its 105 years of sport. But it’s not just been used by the Cubs; it has played host for NFL games, ice hockey and even ski jumping in 1944. Constructed in just four and a half weeks for $250,000 by 500 men, it is quite a sight to behold, as are the additional 3,000 seats perched on the adjacent rooftops, giving fabulous views of the field below.

If you want to check out the performing arts scene in Chicago, do not pass go if Hamilton is showing! It may be one of the more expensive treats on your trip, but it is certainly worth forking out for good seats. The story of America’s founding father Alexander Hamilton, an immigrant from the West Indies who became George Washington’s right-hand man during the Revolutionary War, this hip-hop, rap and jazz extravaganza is brimming with astonishing talent and will have you singing and dancing all the way home.

While we’re on the topic of toe tapping, there’s one glaringly obvious thing I’ve yet to mention – blues. Developed in Chicago in the 1950s, blues music has worked its way into the fabric of the city’s soul. Make sure you head to Kingston Mines – the largest and oldest continuously operating blues club in town – to listen to some raw talent. And don’t be shy – dancing is wholeheartedly encouraged by the locals!

Kingston Mines is the oldest continuously operating blues club in Chicago.

Eat like a local

Deep dish pizza, right? That Chicagoan classic of course needs to be ticked off the list at some point. But there is so much more to the epicurean scene in the city. In fact, if you were to start at one end of Chicago and work your way through even half of its repertoire of culinary delights, you’d better be planning a permanent move out there.

Chicago may be known for its deep dish pizza, but there is so much more to explore.

First on the cards is the Big Star in Wrigleyville, which conveniently happens to be right next to the famous playing field itself. A late-night honky-tonk that centres on bourbon, tequila and tacos, this place would make for a fantastic pre-game meal. Or, if you’re not quite lucky enough to bag a seat in the stadium, grab your spot at this lively bar to watch on their big screens – you’ll no doubt hear the cheers from across the street!

If you’re looking to stick to the all-American experience, don’t pass up on an opportunity to visit Portillo’s. Going through the doors of this chain – which started off life as a modest hot dog stand in 1963 – feels like stepping back in time, with retro posters and neon signs adorning every inch of the walls. Hordes of hungry revellers are sure to be lining up for their fill of the classic Portillo’s hot dog and chocolate shakes, eagerly awaiting their number to be called so they can collect their scrumptious prize. It really is like a military operation in there, and worth visiting for the experience of culinary bingo alone.

Portillo’s has grown into a well-known chain, but started off life as a small hot dog stand.

Twin Anchors, a 1930s joint famed for its barbecued back-ribs, was a massive hit in our group, and we unanimously decided it was the most authentic Chicagoan foodie experience we encountered. Also, with the endorsement of A-listers like Helen Mirren and Bill Murray who frequent the diner themselves, what more could you need to convince you to visit? If you’ve had your fill of red meat, head uptown to the Bang Bang Pie Shop for a hearty slice of blueberry pie, or to try their renowned ‘biscuit’ for a sweet afternoon treat.

One of the joys of Chicago, though, is the fact that international influences have merged with American cuisine. The most interesting combination we uncovered was The Berghoff which serves German-American style food – and has done since 1898. The first place to have been granted a license after prohibition was lifted, this restaurant has a very traditional feel to it, and the food is made with love. I can highly recommend their spinach gnocchi with chorizo – a beautifully indulgent abundance of carbohydrate joy.

If you are after a south-east Asian meal to tantalise the taste buds, book your table at Sunda. Here, I ordered a duck fried rice dish which was packed full of salty, crunchy flavour. Afterwards, you can take a stroll down to Navy Pier – the iconic 3,300ft-long pier along the shores of Lake Michigan – to work off some of those calories.

The iconic Navy Pier is a must-see when visiting The Windy City.

Last but by no means least is Hai Sou Vietnamese Kitchen which we visited for an alternative to the classic avocado and egg brunch. From tender chicken wings that fall off the bone to Vietnamese omelette with papaya and ‘cilantro’, nobody will be leaving hungry. Make sure you leave room for their vanilla custard and egg coffee – a warming hug in a mug – as well as their delicious lychee Danishes.

See the sights

As the home of notorious gangster Al Capone, who incidentally made around $60m per annum supplying liquor to thousands of speakeasies in the late 1920s, Chicago is a city that knows how to get the party started. It even boasts a gold-topped building that was designed to look like a champagne bottle in protest to the times of prohibition. So, as well as visiting one of their many cocktail bars – I recommend Cindy’s Rooftop Bar for anyone who likes a bonnie view – you can’t miss out on the Chicago Crime Tour to fully appreciate Chicago’s party-packed, blood-soaked history.

Cindy’s Rooftop Bar boasts views of Millenium Park and Lake Michigan.

Taking you through the St Valentine’s Day massacre of 1929, robberies gone wrong and all manner of gangster tales that gave the city its notorious reputation, you’ll find yourself standing at dozens of former crime scenes. You’ll even hear stories from more recent times, stretching into the 90s – when ordering a McDonald’s ‘Happy Meal without the toy’ had the potential to earn you a night or two in a prison cell.

If gore’s not your thing, there is a spectacular way of drinking in some of the city’s architectural history, and it’s a rather civilised affair. Sweeping down the Chicago River that carves through the city centre, First Lady Architecture River Cruises will talk you through over 50 buildings in 90 minutes. After the great fire of 1871 burned much of the city to the ground, some of the world’s greatest architects gathered to rebuild it, creating a beautiful melange of Parisian Art Deco-style buildings, 20s Beaux Arts structures, 1980s post-modernism and more.

For the braver souls – or those looking to get the heart racing – the Skydeck is bound to get the adrenaline pumping. After whizzing up 103 floors and 1,353ft, you’ll find spectacular 360 degree views of the city, spanning up to 50 miles and four states on a clear day.

The views from the Skydeck are unrivalled on a clear morning.

Like me, you may find yourself coerced into stepping into the glass boxes which reach 4.3ft out from the deck – just don’t look down…you’ve been warned.

Whatever you do, don’t look down when you’re on the Skydeck…

Five days went in a flash, but when there’s a will to eat, drink and tour your way round Chicago, there’s always a way. If you’re looking for a holiday after your summer holiday, I can’t think of anywhere better. And I, for one, will be back very soon.

For more information and tips, visit the Choose Chicago website and social media pages. @ChooseChicago