Last Updated on January 21, 2026 by Home in the World
I have noticed that many non-Americans who visit the USA as tourists tend to stick with the two coasts. They will generally have visited Los Angeles, San Francisco and Las Vegas in the west, and New York and Florida in the east. Perhaps even somewhere like New Orleans in the south.
But ask them if they’ve been to Chicago – home to blues music, an iconic NBA team and a thriving theatre scene – and most will say no. They’ve heard of it, of course, but it had never really occurred to them to visit.
I was the same. I had been to the east and west coasts multiple times, but had somehow bypassed one of the USA’s largest cities. Indeed if I hadn’t had friends to visit there, I may well not have gone at all. In any case, I eventually found myself landing into the world’s sixth busiest airport, O-Hare, on a chilly spring evening, all set to see what America’s Midwest had to offer.
There is admittedly only a handful of ‘tourist sites’ as such in Chicago; it’s more of a place to just wander around, soaking up the big-city vibe and captivating architecture. It reminded me quite a lot of New York, minus the extra hype. (And by the way, if you’ve ever wondered where the name Chicago came from, it’s derived from a French rendering of the Miami-Illinois word shikaakwa or ‘garlic plant’, which grew along the Chicago River. The city itself was founded by Jean-Baptiste Pointe DuSable in the 1770s).
Read on to find out some of the things I recommend in terms of what to see in Chicago (based on my visit in 2013).
This article is also featured on GPSmyCity. To download this article for offline reading or create a self-guided walking tour to visit the attractions highlighted in this article, go to Walking Tours and Articles in Chicago. You can also read more about the GPSmyCity concept in this blog post.
Downtown architecture
And so it was that much of my time in the Windy City (a nickname that supposedly has more to do with the ‘hot air’ spouted by 19th-century Chicagoan politicians, and less with the climate) was spent with my neck craned up, admiring the varied designs and often elaborate façades of the many skyscrapers in the downtown area.
Michigan Avenue
One of the most famous streets cutting north-south through the heart of the city and over the Chicago River is Michigan Avenue, whose upscale section is aptly dubbed ‘The Magnificent Mile’. And magnificent it truly is.
A canyon of glass high-rise and heritage buildings (several of which were pictured above), split down the middle by well manicured median strips (when I visited in spring, the tulips were in bloom).
It’s a mix of office blocks, shops, restaurants and hotels – with traffic density to match. But if ever you were going to feel like you were in a swanky, pulsating metropolis, it would be here.
Not all of Chicago is like this, of course. Pockets of the ‘South Side’ have been well documented in the media for their ghettos and gun violence. Sticking to the main downtown area, however, particularly during the day, felt totally safe – a sentiment echoed by my local Chicagoan friends.
For many people, Chicago is synonymous with the Chicago Bulls NBA team – and, consequently, their star former player Michael Jordan, who happens to own a steak house on Michigan Ave.
By stark contrast, historians and archaeologists may be interested to know that the avenue is also home to a piece of original stone from the Great Pyramid of Egypt, dating back to 2600 BC. It is one of several famous stones from around the world to have either been gifted to Col. Robert R. McCormick, editor and publisher of The Tribune, or obtained by The Tribune‘s foreign correspondents.
The Cloud Gate (a.k.a. The Bean) and Millennium Park
For all Chicago’s grand buildings, however, one of its most photographed structures is arguably a stainless steel sculpture known as the Cloud Gate (or ‘the Bean’) designed by Indian-born British artist Sir Anish Kapoor.
It stands in the large urban space known as Millennium Park, and is a magnet for selfie-takers and creative photographers. Pieced together using computer technology, the 168 steel plates making up its curved surface bend and warp the city skyline and clouds, generating unique angles and perspectives.
And on the bleak May day that I visited, it wasn’t just the Bean that was capturing my attention. Check out the bizarre low-level mist that hung over the city just a few metres away, enshrouding the tops of several buildings:
Art Institute of Chicago
When you’re finished snapping your arty shots at the Cloud Gate, I highly recommend spending a few hours in the nearby Art Institute of Chicago.
I went in partly out of interest and partly to shelter from the rain and cold, and boy was it worthwhile.
It can rightly be considered one of the world’s great art museums, with pieces ranging from ancient Tibetan artefacts to modern Warhol works. It is well laid out, spacious, and the mobile app you can use as a guide worked very smoothly. One of the best museums/galleries I have visited anywhere in the world.
Navy Pier
Situated on the shores of Lake Michigan and straddling the Chicago River, Chicago is also a suitable destination for those who enjoy being out on the water.
The main attraction in this respect is Navy Pier – an entertainment precinct stretching along a 1,000-metre-long (3,300 ft) pier. There’s a mini amusement park, a Ferris wheel, countless dining options, and even an IMAX theatre. It’s crowded and, in my opinion, quite tacky – but it is what it is.
Cruise on Lake Michigan
My main reason for going there was because it is also the departure point for cruises on Lake Michigan, which give you a great, unparalleled view of the stunning Chicago skyline from the water. From memory the cruise only lasted about an hour or so, but it is a great way to breathe in some fresh ‘windy’ air and admire the high-rise panorama.
Architecture boat tour on the Chicago River
For another water-based experience in Chicago, I also recommend doing an architecture boat tour down the Chicago River. The cruises depart near Navy Pier, and offer a different perspective (not to mention guided commentary) of the city’s prominent buildings, many of which have already been pictured in this blog post.
Willis Tower (formerly Sears Tower) and John Hancock Center
Among Chicago’s sea of skyscrapers is the 110-storey Sears Tower (now officially known as the Willis Tower), which held the title of the world’s tallest building for nearly 25 years. It is still the second-tallest building in the USA and Western Hemisphere – and the 16th tallest in the world.
You can visit the Skydeck there for a bird’s eye view of the downtown area and beyond. I, however, opted to go to the Observation Deck on the 94th floor of the 100-storey John Hancock Center, located at the northern end of Michigan Ave; it is almost the same height, and still offers great views of the city, including the Sears Tower itself.
Theatre district
Finally, a visit to Chicago wouldn’t be complete without a stroll through its famed theatre district. Let’s not forget the city even has a musical named after it.
The Chicago Theatre (originally known as the Balaban and Katz Chicago Theatre) is designed in Neo-Baroque/Neoclassical style, and its iconic marquee has featured in a number of films, television shows and works of art. I did not attend any shows there, but its website provides information on current and upcoming gigs.
Final thoughts on what to see in Chicago
So is it worth straying from the usual coast-to-coast itinerary and adding in a stop in Chicago on your next US travels? I would definitely say so.
It’s classy with a dash of urban cool and big-city brashness. Sure, there are some less than savoury parts, but from a tourist perspective, I’d say it’s an underrated gem when it comes to American metropolises.
It’s a haven for lovers of architecture and street art, a cradle of music and theatre, a good choice for sports fans (Chicago Bulls, Chicago Cubs etc.), and a Mecca for those partial to the famous Chicago-style deep-dish pizza (I don’t eat cheese, so unfortunately there wasn’t much point in me trying it). It’s basically a lower-key New York. I think you’ll love it.
** This post, like everything else on this website, has been written entirely by me. No ChatGPT or any other AI tool has been used. It takes longer to create, but I value 100% human-generated content and I hope you do too! **
Trip facts
When I visited: May 2013
Weather: I visited for 4-5 days at the end of May, and the weather was fickle. The first day was clear but freezing by my standards (a daytime maximum of 8°C/45°F), while other days were slightly warmer but rainier and sometimes quite foggy. By the end of the stay, it was quite pleasant. Overall, I would still recommend it as a decent time to visit. Summers can get quite hot and humid, while winters are brutal with heavy snow.
Where I stayed: Kimpton Hotel Palomar (which is now the Royal Sonesta Chicago River North)
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