Top Things To Do in Chicago: A Weekend Guide


Chicago is a huge city and a fairly popular one in North America; and though last year alone I transited through the city 14 times I had never actually set foot outside of the airport. So needless to say, I was quite curious and excited to grab a camera and have my cousin host me while I played tourist in a city the size of Toronto.

I absolutely loved it!  Chicago has all of the architectural wonders, nightlife, and food scene of New York City but it is matched with the history, class and feel of London – plus there are a lot of parks, piers, colors, and squares so you never feel as congested as you may in Manhattan.

There are 7 things I would definitely recommend doing if you are in the Windy City for a brief period of time.  There are many more but as I grew up in a household of artists I try not to see every museum each time I go away, so the reason those are left off isn’t because I am culturally daft, but more so because I like to admire a different form of art – that which is visible outside.


So if you have two days in Chicago I recommend these 7 things:

1. Have Pizza

More specifically, have pizza at Giordano’s, this popular and famous deep dish style pizzeria serves you more of a pie than it does a traditional pizza. You will wait about 35 mins (while this may seem long it is completely worth the wait, and when you see the size of this thing and how much cheese exists in it you realize cooking time is key) and when you finally taste it your mouth erupts into fireworks at what is quite possibly the best mix of crust, cheese, sauce, sausage, onion and pepper ever.  It really is great, I think the proper term is stuffed pizza, but basically its a platter of awesome. The pies themselves are quite heavy (both weight and content wise) so my cousin and I took the second half of our pizza to go, and here is how I know it is a good pizza – it tastes just as good for breakfast the next morning. If you are in the windy city – allocate at least an hour of your day and check them out:


2. Picnic

Walk over to the Planetarium (again this is a situation where if you want to go in – by all means do so) and sit outside eating a sandwich while you are mesmerized by the magic that is the Chicago skyline. It is very comforting and soothing just to sit there (the gorgeous weather we had definitely helped) and star out on the various eras of architecture – just beautiful & having freshly baked cookies also helps with the whole experience


3. Sit Under the Cloud Gate with a Camera

This sculpture, which is part of Millennium park, was built in 2004 with an original proposed cost of $9 million yet somehow ended up with a price tag of (wait for it) $32 million which obviously  was not well received originally by the tax payers of Chicago. It’s beauty has since smoothed things over with Chicagoans? Chicagoites? Chicagans? (one of the above). It is made up of 168 stainless steel plates welded together with a highly polished exterior (covered always in finger prints) that has no visible seams. Really beautiful – and if anyone has ever seen the movie “The Sphere” it has a similar effect of leaving you staring in wonder as you marvel at it’s construction and seamless beauty.


4. Walk Around Navy Pier

like most seaside cities Chicago has that cheesy tourist spot with trinkets, rides and games galore. However there’s is done with a little bit of class, yes there is a Ferris wheel, boat ride, and the overly large sized McDonald’s but like the rest of the city it isn’t densely littered with stands or buildings and it’s sparsity gives you a feeling of being a child again walking through a playground. It is colorful, fun, and by the water – simple but really all I need in life

(ps for an added bonus go inside the food stand to Gorton’s Popcorn and order the Chicago mix – your taste buds will thank you for this delicious mix of caramel and cheese that you would otherwise think is impossible to blend together)


5. Take an Architectural Cruise through the City

it really is a city full of architectural wonder – there are buildings from various designers that all compliment each other, and even the Trump tower was built to play homage to the three buildings in it’s surroundings. An archictural cruise will take you on a boat that allows you to see the city from the river and navigating under many of its 38 bridges. The guides are very fun and informative and it  is great to learn the history of buildings, architects, designers and the city itself while you take close looks at buildings you admire from the great vantage point by the Planetarium


6. Have a Drink at the Signature Room

Nothing feels more rewarding than having a cocktail on the 95th floor of the John Hancock Building after a full day of sightseeing, the views are incredible and you can a panoramic display of beauty that is Chicago. Note if you are a female, the very best view comes from the ladies’ washroom which is unobstructed and kept spotlessly clean.


7.  Visit Buckingham Fountain

a.k. the fountain in the opening credit of «Married with Children», and while the show was never one I enjoyed the fountain is beautiful and creates a beautiful centerpiece to the skyline behind.


While I am sure there are a million more things to see in Chicago, and I will go back to slowly start making that list shorter and see the family more frequently these are the ones I would recommend for travelers who, like me, save money with ridiculous stop overs and have a few hours to spend in Chicago.

If you’re also there for a short time and want to pack in as much as possible, I’d recommend geting a Chicago cityPASS or joining a Hop on Hop off bus tour – they cover the main highlights of the city.

It really is a beautiful city and I cant wait to see more of it on my next layover!

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