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We are all programmed to dream of the Big Apple and the Windy City – from brownstones and Broadway, to Cubs baseball and deep-dish pizza. Visiting from South Africa, it truly feels like living the American Dream. I recently had the privilege of spending a whirlwind week travelling between these two beautiful, yet wildly different cities and what follows is an enthusiastic, first-timer account of that time I, too, got to live the American Dream in New York and Chicago.

New York, New York

We arrived in a balmy New York on a Friday afternoon. Grabbing a taxi at JFK airport (after surviving one of those hellishly long lines at passport control), we made our way to Manhattan. I’ll never forget seeing the skyline for the first time! It was like seeing Woody Allen’s Manhattan come to life before our very eyes.

I was extremely lucky to have a seasoned New Yorker as a travel companion, as I am not a big fan of the tourist attractions and would much rather experience New York the way a real New Yorker would. We, therefore, stuck to walking through Central Park, across Columbus Circle, down Fifth Avenue and then took the Subway to Little Italy, Chelsea, coming back through Hell’s Kitchen.

In Little Italy, we attended the San Gennaro festival, which to me was definitely a highlight. The street was bustling with thousands of people walking up and down the stalls. We had true New York pizza (which is better than Chicago’s – sorry Mid-Westerners!), cannolis and a huge variety of other street food that I cannot even pronounce.

From there, we meandered onto Chelsea where we raided a Milk Bar (yes, the Netflix Chef’s Table Milk Bar) – where we had cereal milk ice cream, fruity cereal shakes, b’day cake shakes, and of course crack pie! What a whirlwind; by the time we reached Chelsea Market we were ready to sit down and do some people watching. I have to say that New Yorkers are very interesting, busy people and I can watch them for hours.

Another highlight is the crazy, beautiful, overwhelming Times Square. I’m so glad that I got to experience it in both day and night time as it is a wildly different setting. There are people in costume, tourists, people singing, city sounds, huge billboards, skyscrapers, colours and so much more. If you can find a little space where you can just take it in for a second, I really encourage you to just stand still and breathe it all in. If you ever find yourself in Times Square, be sure to pop in at Virgil’s for a Southern barbeque – even for a Free State girl, the meat was pure heaven!

In a weekend of life-changing highlights, watching Beautiful: The Carole King Musical was something I’ll never forget. Think of any and every theatre piece you’ve ever seen in South Africa and multiply that by a thousand. Honestly, that doesn’t even come close to the production value, actors, costumes, sets and more.

New York is such a once-in-a-lifetime experience, I think you can live there for years and not even experience all the city has to offer. If you ever get the opportunity to visit, definitely do!

The City by the Lake

So I have to be honest… I fell completely head-over-heels in love with Chicago. The city is romantic, more subtle, leafy and less of a hustle and bustle. The buildings are beautiful – their University library is a must-visit – and the skyline along the lake is amazing to behold!

Chicago is also a city of art. The Art Institute of Chicago is home to one of the biggest impressionist collections in the world and we saw several greats like American Gothic and Nighthawks. They also have quite an extensive modern art section, which are always conversation pieces.

The Windy City is also best to explore on foot. We strolled along the Magnificent Mile in the pouring rain, and to me, the city was even more beautiful in the drizzle. A definite highlight was visiting the three-story American Girl shop. The shop is an arrangement of different dolls – big and small, each with her own personality and story. There is even an entire coffee shop dedicated to having a tea party with your doll. The little girl in me totally lost her shit!

More or less all of this forms part of Downtown Chicago, but trust me, this is not the only part of Chicago you need to visit. When we first arrived in Chicago from New York, we were tired and overwhelmed. I got us an Airbnb in Wrigleyville, a suburb of Chicago. Yes, you guessed it, it’s the suburb close to the world-famous Wrigleyfield stadium.

This family-friendly neighbourhood is one of the most charming places I’ve ever been to. And the people are amazing – kind and friendly and helpful. There are families everywhere, people jogging in the street, having a drink with friends. The streets are well-maintained and the area is leafy and gorgeous. We walked from one bar to the next in order to experience it in full, and because it is such a contrast to the busyness of the Big Apple we had a second to gather ourselves and enjoy true Mid-Western hospitality.

Seeing these two cities is something I’ll never forget. They are two different tastes of the US and each one leaves you in awe. Being able to travel and experience these wildly different cultures is truly a privileged experience.

Ohh yeah, if there is one recommendation I can make – don’t miss having dinner at The Publican in Chicago – it’ll change your life!

We also made an awesome video of our trip – have a look!

Keen for some more travel inspo? Click here


Free State-girl, living in Stellenbosch. Love to explore small towns, read in Afrikaans and everything pop-culture. My favourite yoga move is 'The Pigeon' and one day I'd like to own my own vintage cinema.

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