Chicago has become my favourite US city. It has stiff competition from San Francisco and New York but the scales tip towards the Windy City.
When to visit
Winters are unforgiving in Chicago. Unless you’re OK with the wind and cold, I suggest visiting in spring and summer. We were there in late June and we got sunny pleasant weather, not too warm.
The best thing you can do is to buy a CTA/PACE fare card for the subway, buses and the L. We bought ours at O’Hare airport. The new card cost $5 and a seven day pass, $33 each.
Riding the L is fun! Go round the Loop, the downtown area, in the L (for elevated train built in the 1890s.) The train seems to go in and out and round buildings. I loved peeping into windows and see what’s inside. Make sure you choose the right station to go round in a circle (it’s actually oblong but you know what I mean).
We ended up taking more buses than trains. They go everywhere!
There is no shortage of accommodation in Chicago. We usually stay at a Marriott because we get points for their program. We stayed in the River North area, really close to Michigan Avenue, the river, restaurants, shopping and public transport. It was a fantastic location.
Chicago architecture tour
We took the Chicago Architecture Foundation river cruise and we absolutely loved it. A very enthusiast volunteer docent from the foundation told us the history of Chicago through its buildings. It is well worth doing.
Since Chicago is known for its pizza, we decided to take a pizza tour. It included four different styles of pizza in as many pizzerias. At Pizano’s we had the tavern style (thin crust) and their version of deep dish pizza. They were good but not spectacular. Then we moved on to a place where we had Polish sausage and sauerkraut pizza (very nice) and s’mores pizza (ugh! Way too sweet). My favourite was the Neapolitan style pizza at Coalfire (1321 W Grand Ave). The crust was perfect. The last stop was Pequod’s famous for its deep dish pizza. At the risk of offending hard core fans, I have to say that I didn’t care for it. It was like bread lasagna.
Art Institute of Chicago
The Art Institute of Chicago was recently voted best museum of the world by TripAdvisor so, naturally, I had to see it. The general admission is $25 ($19 if you buy at it 4 pm, but be aware that the museum closes at 5). The highlights are, for me, the Chagall windows, the Impressionists and two iconic American paintings: American Gothic and The Nighthawks. Did I think it was the best museum of the world? No; however, I enjoyed the visit and recommend you do drop by when in Chicago.
From up high
There are two very tall buildings in Chicago: the Willis Towers (formerly Sears) and the Hancock Center. The Willis Tower has two observation decks: the Skydeck and The Ledge, a glass platform. No, thank you! I don’t like heights that much. We went to the bar on the 95th floor of the Hancock Center. It’s a nice place –however touristy- place for a drink and fantastic views.
Walk, walk, walk
Chicago is a very walkable city. which I love.
Have you been to Chicago? Share your own recommendations in the comments below.
Hi, I’m Ana. I’m originally from Argentina but I’m currently living in Dallas (USA) with my British husband. I’d like to share my experiences as an expat and as a traveller.