Deep dish pizza, queuing for the view from the world’s former-tallest-building and cruising the Chicago River
Last time out, we took a look at our time in Chicago’s Loop and its parks. Read on to see what else we got up to in the Windy City. You can also watch all that we got up to here, or below.
Took in the stunning Chicago skyline with an architecture river cruise
Cruises aren’t just for old people, as this proved. The Chicago River is at the heart of the city. Of course, there are plenty of operators wanting to take your hard earned dollars off you, but we went with the Chicago Architecture Foundation due to their not-for-profit nature.

The cruise gives you history of the city by pointing out notable buildings, of which there are many, up and down the river. You’ll see buildings, or perspectives, which you won’t see if you stay on dry land. Oh, and if you’ve heard that the Chicago River flows the wrong way, but aren’t quite sure if it’s true, then the cruise will tell you more!


Peered down on the city from the Willis Tower

Do you love queuing for hours? Then the Skydeck at the Willis Tower is for you!
We arrived on Sunday evening at 6:30pm. The queue snaked around two sides of the block. Our prepaid tickets didn’t allow us to skip any of the queue, and we were told that it would be three hours until we were at the top. Given it closed at 10pm, we really didn’t think it was worth it.
So we returned the next day, over 30 minutes before opening, but still waited over an hour to get to the top (although only over 30 mins after opening). Along the way we passed several tortuous looking queuing systems, like those you see at theme parks.

Once at the top there was yet another queue of 10-15 minutes to experience the glass boxes which hang out over the city 412 metres (1,353 feet) below. Once in the box, you felt so pressured by the waiting hoards behind you, that the enjoyment was diminished.


The view of the city is good, but the view is interrupted in places by the building’s structural columns and window frames, whilst space is limited for such a popular attraction.
Acquainted ourselves with Chicago’s most famous culinary creation
So I love pizza. But I’ve been put off deep pan pizza ever since chomping through those dry, deep bases of frozen supermarket pizzas. Thin crust Neapolitan style pizza is definitely my preferred type.
If I was to give deep pan, also known as deep dish, a go anywhere though, then it should be in its home town, Chicago. We went on a tour with Chicago Pizza Tours, who took us to four restaurants to sample local pizza. We learnt along the way about the history of Chicagoan pizza, and that the city isn’t all about deep dish – it’s more for special occasions. In fact the majority of pizzerias serve mostly thin crust pizza or no deep dish at all.


At Pizano’s, we had deep dish pizza with a thick layer of amazing cheese buried under a covering of tomatoes. Next up at Flo & Santos, it was onto tavern style pizza (this is Chicago thin-crust pizza, typically cut into a grid of square pieces) – one with Italian beef, one with polish sausage, and finally a dessert pizza. At Pequod’s there was more deep dish, which takes 45 minutes to cook (fortunately ours was ordered in advance!), and finally at Piece, where we finished with American thin crust style. All were nice, and very filling, but I’m still not a convert – Neapolitan thin crust is still the king of pizza!


The tour was great in getting us out into different neighbourhoods and parts of the city beyond the Loop, and experiencing and educating us on different types of pizza. However, what would have really topped it off would have been access to, or a view of, one or two of the kitchens, just so that we could see how these different pizzas are constructed.
Have you been to Chicago – did we miss out on any good sights or experiences?
Stewart
Great photos!
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Thanks! Helps that Chicago is very photogenic!
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I love the idea of the pizza tour!!
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It was fun, and if you like pizza, then it is a little bit of heaven as someone chauffeurs you around to all these pizzerias!
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I didn’t expect to like deep-dish, but I was very nearly a convert after experiencing Pizano’s. One thing I found surprising though was the price of bottles of wine – so expensive compared to the UK!
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Pizano’s is worth it just for the cheese alone!
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