For you this City may conjure up images of Al Capone, Pizza and Prohibition, but for me Chicago goes much deeper than that and it’s a place that has stayed with me since my family had the opportunity to move to the Windy City when I was 11, which at the time seemed like the end of the world to me! However, on arrival I instantly fell in love and did not want to leave. Sadly a year later my family decided it wasn’t for them and we trotted back over the pond and life went back to what I previously knew, although with one big change- my love affair with travel was born! 

Chicago always stuck with me and I knew I would go back one day as an adult… But what to expect? My memories of it were being so cold in the winter that by the time my dad walked me to school he had icicles hanging from his beard and the summers being so hot that we would play cards in the basement to keep cool. 

When I returned I stayed with my family in the suburb of Blue Island Illinois. This is easily assessable by the Bilevel train which services destinations outside of the city. If you are staying within the City there is a very good Metro system

Navy Pier

Blue Island is extremely different to Downtown and I was chomping at the bit to get there. That first view of the city weather by road or rail blows you away! We drove past the famous Navy pier which if you want to view the skyline at night then you should head here and see the City lights in all their glory. 

Riverboat cruise throught the city

Riverboat cruise throught the city

River Cruise

My first recommendation would be a Lake & River tour which travels through Chicago Lock giving you great insight into the architecture of some of the city’s most iconic buildings as well as learning nearly 200 years of history with prime focus on the great fire of Chicago which reigned through the city from 8th-10th October 1871 and culminated in the building of the worlds first skyscraper using a fireproof steel- skeleton construction. The cruise then takes you out to Lake Michigan where you see the full 26 mile sky line in all its glory. For you selfie lovers this is the place to snap. 

Shopping on the Magnificent Mile

If you fancy some retail therapy, then you will find the Magnificent Mile right up your alley!! This is the commercial district where you will find all the best department stores and fashion outlets. Whilst here you can also visit some of the city’s famous landmarks such as The Chicago Water Tower, Neo Gothic Tribune tower (one of my fav’s), the terracotta Wrigley Building and the John Hancock tower (more on this later). 

Willis Tower (formally Sear's tower)

Willis Tower (formally Sear's tower)

Willis Tower & The John Hancock Centre

As a small girl I will never forget the first time I stood at the bottom of the then named Sear’s Tower (now known as the Willis Tower). Standing at 1,4250 feet with 110 floors this was the worlds tallest skyscraper for nearly 25 years. It was completed in 1973 and remained the tallest building in the Western Hemisphere until the rebuild of the World trade centre in 2014. I could have stood looking up at it all day, but my neck had other thoughts! On my return 20 years later, I felt the same feelings looking at it. The structure of it was so ahead of its time and I think many newer skyscrapers in this modern age still can’t compete with it. 

They do have an observation deck on the 103rd floor and on a windy day you can feel the tower sway. In 2009 they installed glass bottom ledges, so you can see straight down if your feeling brave. However, if you want to see the city from above and avoid the crowds then my top tip would be to visit the John Hancock Centre which I have previously mentioned. Rather than queuing with hoards of tourists you can have cocktails on the 96th floor in the Signature Lounge they also have a restaurant on the floor below. You get all the benefits of the city views and Lake Michigan but rather than paying for an observation ticket you can drink a cocktail. You may also run into Oprah Winfrey as she has an apartment here. 

Deep Dish Pizza

You can’t talk about Chicago without mentioning Pizza! The original home of the deep dish and boy are they deep! Gino’s East is one of the best. They have a lot of branches now but if you’re on the Magnificent Mile then you will find yourself in the original and best Gino’s East. Founded in 1966 they make pizza so thick with cheese that you could choke on it (in the best possible way) and they have kept the original graffiti walls that you are welcome to sign and leave your mark behind. 


If you’re into music, then this city has you covered. Famous for its live Jazz and Blues clubs and renowned for some of the best House music DJ’s (The late and legendary Frankie Knuckles originates from here), Smart Bar attracts all the great names and events such as Derrick carter and Secret Sundays. 

Fancy a joke or two? Then head to Second City for some stand up. You might witness a soon to be major star on their way up as big names such as Tina Fey (Saturday night live & 30 Rock) Bill Murray (Ghostbusters & Groundhog Day) and Steve Carrell (Anchor Man & 40-year-old Virgin) all started playing to the crowds here. You can even take classes if you have the time. 

There’s a reason Chicago is the second most visited City in America, and in my opinion I believe it should be 1st. Yes New York has it all and I have visited there also on several occasions, but if you want a city with a bit more character and outstanding architecture then step away from Manhattan and give the Windy City a try it ticks all the boxes and more.