My first time in Chicago – a charming city break full of striking sights and surprising kindness

I wasn’t let down. The Windy City has a small-town, friendly type of feel in a big city. I was struck at how receptive and soulful people were in answering questions and providing recommendations as I walked on the bustling streets.

And what streets! An astounding skyline is something that the USA's third biggest city has and particularly at night time, the buildings light up in a special way.

One way to get a sense of this is by taking one of Chicago’s architectural boat tours, which provide a fascinating insight into the history and development of its buildings. I glided along the river, peering upwards on Chicago’s First Lady, the Chicago Architecture Foundation Center River Cruise (architecture.org).

Of course, you can step inside that skyline too, with visits to iconic skyscrapers such as the Willis Tower (formerly Sears Tower) and the John Hancock Center.

A Batman movie scene in The Dark Knight with Christian Bale was filmed at the top of the Willis Tower as the actor overlooked the city in his cape.

We ate an early morning breakfast in a small group at the Skydeck here (willistower.com), which sits on the 103rd floor and lends itself to breathtaking views.

This was the tallest building in the World when it opened in 1973 and held that title for 25 years.

Randy Stancik, Skydeck’s General Manager, told us about how you can see views of the city spanning up to four states and 50 miles on a clear day.

Batman was just a visitor. Famous Chicago natives include Harrison Ford, Oprah Winfrey, Ernest Hemingway, Walt Disney, Bill Murray and Jennifer Hudson.

Former President Barack Obama and first lady Michelle both hail from Chicago – they own a lovely red brick house located on a tree-lined street in the historic Kenwood near the University of Chicago.

Famous Chicago movies include Ferris Bueller’s Day Off and The Fugitive - good options to watch while having the cityscape surround you. If you’re looking for top class museums, and a movie hit, the Art Institute of Chicago was one stop for Ferris and friends in the iconic 1986 movie.

The iconic Millennium Park is another must-visit while in ‘Chi-town’. It features the famous ‘Cloud Gate’ sculpture affectionately known as ‘The Bean’.

It’s an iconic selfie opportunity in Chicago, and I was taken aback by how the stainless structure reflects the buildings and anything close to it. It is such a striking mirror feature that we checked back to see it again several times on our Chicago trip and is normally thronged with people taking photos.

Millennium Park also has beautiful gardens, and free outdoor concerts during the summer in the heart of downtown Chicago.

Chicago is a food lover's paradise, offering a diverse culinary scene with everything from deep-dish pizza and Chicago-style hot dogs to gourmet restaurants and international cuisine.

Sampling a Chicago deep dish pizza at Lou Malnati's (loumalnatis.com) is a must which we did while on a cycling tour of the city.

We also stopped at Portillo’s (portillos.com) for a classic Chicago-style hot dog. It’s basically an all-beef hot dog on a poppy seed bun, topped with yellow mustard, lots of relish, diced onions, tomato wedges, a pickle spear, sport peppers, a dash of celery salt — and most importantly, no ketchup.

Another foodie highlight was The Oakville Grill & Cellar (theoakville.com). It’s a Napa Valley-inspired restaurant in the heart of Fulton Market District; service was very good and the cuisine delicious.

Lunch at Beatnik on the River (beatnikontheriver.com) gave us an interesting fusion of three culinary styles: Moroccan, French and Italian.

The city’s location on the shores of Lake Michigan also provides a beautiful backdrop for outdoor activities. Visitors can enjoy strolling along the lakefront, cycling, boat tours or even kayaking – a highlight for me was paddling down the shimmering Chicago river in the summer sunshine.

I also started one day with a splash – meeting a college friend for a swim early in the morning.

Kenneth Browne from Gorey, Co Wexford, has been in Chicago for eight years since graduating.

“There is a wide network of Irish people in Chicago,” he told me. “And this is evident any time an Irish artist comes to perform.

“People are always interested once they hear the Irish accent, conversation is positive, and they typically have a dozen questions about Ireland.”

Chicago also boasts a vibrant music and entertainment scene – famously shown in The Blues Brothers. Visitors can enjoy live performances, concerts, comedy shows, and jazz clubs that pay tribute to the city's musical heritage.

We visited Rosa’s Lounge (rosaslounge.com) and cafe to take in a traditional blues show (if you’re looking for a quirkier, speakeasy bar that is peaceful, then The Violet Hour is for you – it serves artisanal cocktails in the heart of Wicker Park; theviolethour.com).

Throughout the year, Chicago also hosts numerous festivals and events, celebrating everything from food and music to culture and arts. We went to the Windy City Smoke Out (windycitysmokeout.com), a BBQ and country music festival, featuring four days of live country music.

And sports?

I caught a baseball game at Wrigley Field. The Chicago Cubs faced the Boston Red Socks, putting on a great show in terms of making sure the spectacle is fun filled.

A baseball game can last around three hours, so it’s important to know that a big part of the experience is enjoying the social occasion and having a chat while watching the action.

Basketball fans will know the Chicago Bulls – Michael Jordan has long since left the team where he dominated the game of basketball, but his legacy lives on. A steakhouse in the middle of the city bears his name and pictures of him flying through the air decorate many restaurants and bars.

There’s so much to do here – and I left with a sense of Chicago as a charming choice for a holiday due to the striking sights and surprising kindness of the people; the way they make your stay feel like a homecoming even if it's your first time there.

As for dying the river green?

That tradition is thought to have been started in 1962 when the local plumbers' union poured a small amount of green dye into the river, turning the water a bright green colour.

Since then, it has become an annual event in the city on St. Patrick's Day. The vegetable-based dye is environmentally safe and naturally dissolves in a few days.

How to do it

Aer Lingus flies direct from Dublin to Chicago (aerlingus.com).

Colin stayed at The Emily Hotel, situated in the trendy West Loop neighbourhood. Its ground floor Fora restaurant has tasty food, and you can watch movies on the 6th floor rooftop outdoor cinema screen. Rooms start from $309/€288 per night. emilyhotel.com

Colin was a guest of Choose Chicago. For more information and things to do in the city, visit choosechicago.com.