Media Partners | Contributors | Advertise | Contact | Log in | Tuesday 9 August 2022

How to spend a long weekend in Chicago


Share This Article:

Our first impressions of Chicago were far from positive. Half of our group had arrived from sunny Boston, and the other half from dazzling New York City, so Chicago had a lot to live up to.

Our first sight of the city was from the train we took from the airport. We passed only faded beige buildings, set against the backdrop of a mottled grey sky, obscuring the magnificent skyline which we would come to know in the following days. By the time we had arrived at our accommodation, we all viewed Chicago as a drab industrial city, devoid of people and the bustling activity which characterises most North American cities.

The next morning we woke up determined to keep an open mind about this famous metropolis. As we wandered closer and closer into the city, under criss-crossing railroad tracks, alongside the glittering river, and in the shadows of gleaming skyscrapers, our positivity was rewarded.

Chicago is a wonderland of culture and commerce, home to one of the most famous art galleries in the world, the headquarters of several enormous North American companies and of course, everyone’s favourite, the bean sculpture.

Oh, and it is a paradise for food and music lovers. You cannot leave Chicago until you have sampled one of their famous deep-dish pizzas and listened to some jazz.

Here are the top places to visit on a weekend trip to Chicago:


Nicknamed “the bean” by locals and tourists alike, this mirror sculpture provides a unique, and distorted view of the Chicago skyline and the clouds above. Check out your wavy appearance and take some insta-worthy pictures at this famous Chicago landmark.  

Take the time to meander through the surrounding Millennium Park, an oasis of calm in the middle of a busy city.

The Art Institute of Chicago

Make sure to dedicate a whole afternoon (or entire day) to this enormous gallery. From contemporary, multi-media exhibits examining the most pressing global concerns of the day, to classic masterpieces, The Art Institute will please everyone. Make sure to check out the current medieval and renaissance exhibition which showcases magnificent pieces of armour, arranged as if in mid-battle.


Get dolled up and catch a Broadway performance at one of the many theatres across Chicago. Hamilton is currently showing, so snatch up those tickets fast!

Chicago Riverwalk

Wander along this pathway in the early hours of the evening to catch the sunset colours reflecting off the water. This romantic and relaxing experience is remarkably quiet since the path exists at a lower level than the main city streets.



Despite knowing little about jazz, a night at The Jazz Showcase transformed me into a fan. Not only were the performers charismatic and unbelievably talented, the venue itself is cosy and steeped in history – this place has been a home for jazz music since 1947.

The Jazz Showcase also organises events for under 21s so everyone can enjoy this authentic Chicago experience.


Recommended by locals, Pequod’s is THE destination for deep-dish pizza. Queues at this popular restaurant can get long so make sure to book in advance. Settle in, grab a beer and relax – the wait for pizza can be long but once you take your first bite, it will all be worth it!

Articles: 29
Reads: 180883
© 2022 is a website of Studee Limited | 15 The Woolmarket, Cirencester, Gloucestershire, GL7 2PR, UK | registered in England No 6842641 VAT # 971692974