Chicago travel tips

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.

Public transport

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!

L tracks


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.

Chicago is an eclectic mix of historic and ultramodern


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.

View from the 95th floor

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.

24 thoughts on “Chicago travel tips

  1. We’ve been wanting to get back to Chicago for awhile. I agree it’s an incredible city with a lot to see and do. I went on the architecture tour and loved it. It’s a great way to see a lot of the city. Oh and the hotdogs! Yum.


  2. I want to go stand on the glass floor that is cracking. It looks like a fun adventure. I might try and work on my base jumping skills while I am at it.

    Great list of things to do in Chicago.


    1. I’ve used the airport as layover but this was my first time here. And I found pizza I liked and some I didn’t, like everywhere else.


  3. We have seen very little of the States, but Chicago is one of the cities that I’m dying to see! The architecture looks so unique and I want to try the deep-dish pizzas! haha. But no, I won’t be going when it’s cold and windy…



  4. I really enjoyed my time in Chicago even though it was April and RAINY and Cold. but I’m from Vancouver … so i can’t complain. would love to get back there to see more of the city! thanks for the info!


  5. I just went to Chicago at the beginning of June! I loved it, but those winters scare the pants off of me. I just don’t know if I would be happy handling it! I totally agree about getting that pass for the trains/buses. So convenient! And if you register your card online, you can actually get the $5 credited. I wish my city would keep up with the public transit. 🙂


  6. this is a very beautiful city chicago………..We have seen very little of the States, but Chicago is one of the cities that I’m dying to see!


  7. Great tips for traveling in Chicago. Having a plan ahead of time is definitely the best way to travel. You can be a lot more productive that way for sure.


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