Chicago: why the windy city beats New York as a US destination - a city guide to Downtown

Home of the skyscraper, Wrigley Field, and deep dish, Claire Schofield argues why the Second City is a better destination than the Big Apple
The Cloud Gate sculpture, popularly known as the bean, with Chicago's skylineThe Cloud Gate sculpture, popularly known as the bean, with Chicago's skyline
The Cloud Gate sculpture, popularly known as the bean, with Chicago's skyline

As I stood on a Perspex ledge 1,300ft above Chicago, I knew this city was a special place. Once the unnerving knowledge that only half an inch of acrylic glass stood between me and the ground stopped feeling frightening, I could look out and appreciate the view before me.

The 103rd floor of the Willis Tower boasts a spectacular vantage point to take in the endless array of skyscrapers that make up Chicago’s city centre, each standing tall overlooking Lake Michigan, which glitters in the distance.

I’m told on a clear day it’s possible to see views of up to 50 miles and four US states from the Skydeck at the top of the tower, although the weather was sadly a bit overcast when I visited - but the views were sensational all the same. Needless to say, I’d recommend braving a trip to the top of the tower just to get a real sense of where you are.

I went to Chicago and it was better than New York (Photo: Claire Schofield)I went to Chicago and it was better than New York (Photo: Claire Schofield)
I went to Chicago and it was better than New York (Photo: Claire Schofield)

Chicago: a metropolis with a buzz but not a bustle

Back on the ground, Chicago is a maze of tall buildings that house designer shops, theatres, museums and bars. The city gives off an indescribable buzz as you walk through its streets I can’t quite explain - it felt lively and I was never quite sure awaited me around each corner. But what struck me most was how much the city reminded me of New York. It’s so similar, yet so different in many ways.

Unbeknownst to me, Chicago is actually the original home of the skyscraper – not New York. After the Great Chicago Fire destroyed around four miles of the city in 1871, the previous wooden structures were instead replaced by giant constructions made of steel and stone and from the ruins, Chicago gave the world its first skyscraper in 1885 – the Home Insurance building. The building boom saw the city usher in the skyscraper era which soon sparked a similar trend around the world. And while Chicago has a similar sense of grandeur as the Big Apple, it feels calmer, cleaner and less overwhelming.

The view from the 103rd floor of the Willis Tower (Photo: Claire Schofield)The view from the 103rd floor of the Willis Tower (Photo: Claire Schofield)
The view from the 103rd floor of the Willis Tower (Photo: Claire Schofield)

Dublin pre-approval: a diversion that will save you time

I only had a fleeting five days to soak up all the city had to offer, but I left feeling like I knew Downtown Chicago well. Travelling to the States was a breeze too - I took a flight from London to Dublin, and then onto Chicago. While this might sound like a faff, I cannot stress how much easier it is to clear US customs in Dublin. The queue was practically non-existent and I’d passed through all of the scary security checks within about 10 minutes.

It saves you time on the other end as you can walk straight off the plane and collect your bags, without having to queue through immigration alongside. It means your holiday starts straight away and I felt relaxed knowing I’d done the hard bit as I boarded that eight and half hour flight.

Where to stay in Downtown Chicago

Once I’d crossed the pond, I stayed at the CitizenM Downtown Chicago hotel which was ideally located for exploring many of the city’s main attractions, with most easily accessible on foot.

What to do in Downtown Chicago

Millennium Park was just a stone’s throw away so I made this one of my first ports of call.

The surface of the Bean was inspired by liquid mercury and reflects people moving around the park (Photo: Claire Schofield)The surface of the Bean was inspired by liquid mercury and reflects people moving around the park (Photo: Claire Schofield)
The surface of the Bean was inspired by liquid mercury and reflects people moving around the park (Photo: Claire Schofield)

The park, known as the “front lawn” of Downtown Chicago, is home to the striking Cloud Gate reflective steel sculpture, best known as “the bean”. It’s a bit of a bizarre attraction admittedly, but I couldn’t help feeling somewhat in awe of it. It manages to blend into the surroundings perfectly and is a real tourist trap for snapping photos.

The American Writers Museum is also worth a visit. It serves as a celebration of American writers throughout history and explores the influence popular works have had on our lives today. It’s packed full of famous quotes and interactive displays that pay homage to some of the greatest pieces of writing ever penned, including song lyrics, poetry, speeches and fiction.

If the aforementioned Skydeck petrifies you, there's a more down-to-earth means of exploring Chicago: get yourself on a bike and get to know the city on two wheels. I took a trip with Bobby’s Bike Hike and it was easily the highlight of my visit.

Chicago is situated on Lake Michigan, one of the five Great Lakes of North America (Photo: Claire Schofield)Chicago is situated on Lake Michigan, one of the five Great Lakes of North America (Photo: Claire Schofield)
Chicago is situated on Lake Michigan, one of the five Great Lakes of North America (Photo: Claire Schofield)

The company offers various bike and walking tours around Chicago so you can pick and choose what you’d most like to see. I opted for the Bike, Bites and Brews Tour which combined cycling with food and drink - a perfect combination, no?

The 13 mile ride took four hours in total and toured the likes of Lincoln Park - which is bigger than Central Park in New York, covering 1,200 acres - Wrigleyville, which is home to the historic Wrigley Field stadium, and the original Playboy mansion in the city’s Gold Coast district along the way.

Chicago’s historic Wrigley Field stadium and Wrigleyville Dogs (Photo: Claire Schofield)Chicago’s historic Wrigley Field stadium and Wrigleyville Dogs (Photo: Claire Schofield)
Chicago’s historic Wrigley Field stadium and Wrigleyville Dogs (Photo: Claire Schofield)

The sights were interspersed with several food stops, including treats at Molly’s Cupcakes, Chicago-style hotdogs at Wrigleyville, and the famous deep dish pizza at Lou Malnati’s. Personally, I found the deep dish style a bit much to handle - it’s a lot of sauce packed into a pie-like crust, and while it is gloriously cheesy, I’d say one slice is probably enough.

Speaking of food recommendations, there’s no shortage of options, but a few places did stand out to me. Time Out Market is fantastic. It’s essentially a large street food-style hub which brings together some of the city’s best food and drink offerings under one roof.

From classic American burgers and BBQ, to Indian, Greek and Lebanese options, it’s a foodie heaven. I opted for a Chicago-style Philly cheesesteak sandwich which was mouth-wateringly good, followed by a monster-sized doughnut and a cup of tea, because you can take a girl out of Britain, but you can’t take Britain out of the girl.

Time Out Market in Chicago is brimming with exciting food options (Photo: Claire Schofield)Time Out Market in Chicago is brimming with exciting food options (Photo: Claire Schofield)
Time Out Market in Chicago is brimming with exciting food options (Photo: Claire Schofield)

For something a little more refined, try Bronzeville Winery. An independent retail and community art space designed to give guests somewhere to socialise, network and relax, while enjoying a fine selection of seasonal food and drink. The restaurant features a revolving art collection and provides guests with live music entertainment while being wined and dined.

My fellow diners and I opted to sample a bit of everything on offer, from cheesy flatbread and duck breast, to brick oven roasted mac and cheese. Hell, even the sprouts tasted good. If you’re looking for a laid-back evening eating fabulous food, I can’t recommend this place enough.

Bronzeville Winery has a relaxed atmosphere and delicious food (Photo: Claire Schofield)Bronzeville Winery has a relaxed atmosphere and delicious food (Photo: Claire Schofield)
Bronzeville Winery has a relaxed atmosphere and delicious food (Photo: Claire Schofield)

Chicago by night: jazz music and cocktails

After evening entertainment? Go and throw back a cocktail while taking in some live music for the night. The Bassment in the River North neighbourhood is one such option. Accessed via a somewhat dodgy looking rusty secret door, what lies behind it is a funky live music cocktail lounge, one of the city’s hidden gems.

You can choose to join the crowds and enjoy the live action in front of the stage, or take a backseat in one of the private seated areas where you can order a pitcher of cocktails that will see you well into the night. Blues club Buddy Guy’s Legends is also a great night out and while slightly less chaotic than The Bassment, it had a special kind of magic about it that gave me a glimpse into Chicago’s music history.

So with its museums, parks, restaurants, bars, theatres, shops and stunning lakeside views, it is baffling how Chicago is to be much less travelled on the US tourist trail than the strikingly similar New York (it has approximately 30 million visitors a year, as compared to New York's 66 million).

Chicago has just as much to offer but the atmosphere is less frantic, there aren’t swathes of taxis and cars hooting their horns, the locals are super friendly and everywhere is so damn clean. It has all of the ingredients for a perfect city break.

Aer Lingus to Chicago

Customers can fly from the UK to Chicago via Dublin with Aer Lingus and benefit from US Customs and Immigration pre-clearance in Ireland, allowing them to arrive in the US as a domestic customer and save time on immigration queues.

The carrier offer up to 14 weekly flights to the ‘Windy City’. Economy fares start from £229 return and Business Class from £1179 return, including taxes and charges, visit: aerlingus.com.

For more information about Chicago, visit www.choosechicago.com.