As a way of getting your bearings, standing 103 floors above a city in a glass-bottomed pod attached to one of the world’s tallest buildings is certainly an eye-opener.
The sensible part of your brain is telling you “this is not normal, go back, go back”, while the adventurous part is telling you “look down, look down!”. That’s the sort of experience you can find at the Skydeck, at the top of the Willis (formerly Sears) Tower in Chicago.

You can see just how big “Chicagoland” is, and indeed how far it stretches around Lake Michigan. The city population of nearly 3 million people live in over 200 neighbourhoods, each with its own sense of community and place.

I centred my recent visit to the city on just two of those neighbourhoods. The first was The Loop, which is the central business area of the city and the second was Wicker Park, a residential area.

As you fly into Chicago, and the city and its suburbs stretch as far as the eye can see, the first thing that strikes you is that the Skyscrapers the city is renowned for can all be seen grouped together in one relatively small area surrounded by the lake and river. You get a different perspective on the ground while contemplating the reflections in the Cloud Gate sculpture in The Loop.

In reality, the artwork is a 110 ton stainless steel jelly bean which reflects and distorts the city skyline as you walk around and underneath it. The other perspective you get is the feeling of déjà vu, probably because the area is one big film set and has been seen in countless movies. The Loop is also close to Navy Pier, which is where Chicago residents go to party. A seemingly endless row of restaurants, entertainment venues and a huge fairground reach far out into the Lake.

The pier is also a dock for the many cruise boats and water taxis which ply their trade around the waterfront and river areas. The river allows for some extraordinary views of the landmark buildings and a tour is well worth considering.

Chicago’s public transport system is excellent and it allows easy travel around the city. Wicker Park is 10mins by train from the financial district in The Loop, but it is a totally different world of delicatessen’s, loft studios and ‘mom & pop’ cafes . In this one area you can buy a traditional Chicago Hotdog from George’s, a 60 year old family business, or try an icecream made to order with liquid nitrogen from the totally unique I-Cream store.

On a Chicago Food Planet tour, you learn that only 20 years ago this area was one of the most deprived parts of the city but re-invented itself as an area for the creative arts. Now, its properties are some of the most expensive in the region and designer shops are side by side with artist galleries and quirky restaurants. If, like me, you enjoy getting a ‘feel’ for a place, it’s an excellent area to spend some time. Not only that, but it is off the usual tourist trail, so you get to see the ‘real’ Chicago.

Courtesy of American Holidays, I stayed at the Hotel Allegro. The hotel is very well appointed, and the rooms offer some great views of the nearby skyscrapers. It is just a couple of minutes’ walk from a train station, which allows for easy access to most parts of the city. However, the main sights, like the Willis Tower and Millennium Park are only 10 minutes’ walk away.