I have always wanted to go to the windy city i.e. Chicago, IL. After New York City and LA, Chi-town is one of the top tourist city destinations in the USA for many reasons. Known for its foodie attractions, home to the blues and located by the water – this town has a chill vibe with lots to do. It’s not as fast-paced as NYC, and we wouldn’t want it to be. Chicagoans have an easy going attitude, wearing casual clothes to top restaurants or cheering on one of their favorite sports teams (The Cubs, Bears, Blackhawks, White Sox or Bulls!); they never seem to be too startled. Their city offers a broad range of activities that we had the chance to get a taste of over the holidays.

Yes – the weather is “cold” but for a Montrealer- it’s more than OK to walk around in and enjoy, even in December. First stop – the famous Cloud Gate aka the “Magic Bean.” Shiny and mirrored all around it’s a hypnotizing attraction. A piece of Art made popular by being included in almost every Chicago-based movie made in the last decade. You see yourself in the bean well enough that you can take a selfie but good luck avoiding all the other tourists! It’s located in the middle of Millennium Park and behind it – a skyline that showcases some of the city’s amazing architecture. We made sure to walk around and look UP at all the details and design variations in the buildings. Just beautiful!
Less than 100 meters away, you can visit one of the best museums in the world, the Art Institute of Chicago. This large building has just about every type of Art from every time period (think the MET or the Louvre). Our favorite collection was probably the Impressionism wing. Monet’s Water Lilies (my fav) and other favorites from Renoir and Van Gogh were presented. Not too far away, you can find the MCA ( Museum of Contemporary Art of Chicago) which has its own charm. Not as immense as the Art Institute – it was a great addition to visiting the most important contemporary art perspective in this cultured city.
Deep Dish Pizza. It’s been a “lifelong dream” for me to try this Chicago dish and luckily, was not disappointed. We made sure to try one of the city’s best at Giordano’s, a popular chain in the city that serves it. Why hasn’t this been exported to other cities? We questioned this as we left the restaurant fully stuffed with the goodness it was. Mmmmm it was not as “greasy” or “thick” as some may expect. The sauce is on top of the cheese that is on top of the toppings. The crust goes straight up near the edges instead of flattening out wide like we know it. For some reason, this changes the whole experience, and after 45 minutes wait for your pizza (it takes forever to cook), you will eat two slices (MAX) and be very satisfied.
ZooLights. This is a cute play on words to say that that Chicago’s public Zoo located in Lincoln Park creates an event during the holidays showcasing a light show. Completely over the top, the zoo places colorful lights that include (but NOT limited to) flashing Santa Clause with his reindeer and synchronized monkeys “swinging” over you. With lots of fun music to keep you going – you will go from being surrounded by a stunning light show to seeing a lion sleeping, gorillas playing or a giraffe eating in different indoor enclosures. In my opinion, it’s an astonishing experience. Totally free, you can see why this is popular for just about anyone.
For the cultural traveler, another top activity here is to watch live blues. With a 10$ cover, you get to witness an authentic group play and sing their hearts out. They also share some great storytelling with the crowd which makes the experience more personal. The small venue was packed even on a Monday, and it definitely felt like a special experience that expressed the city’s soul.
Located on Lake Michigan has its aesthetics advantages. For one, Navy Pier, a city landmark, is just beautiful to visit. A Ferris wheel, a theater, lots of restaurants and shops, you can also take a ferry to see the city’s skyline better. With all its tourist attractions it’s the most visited place in the city, always full of people but enjoyable nonetheless.
Chicago also has some great shopping (the Magnificent Mile), Michelin star restaurants (e.g. Alinea) and skyscrapers with breathtaking lookouts. Well, known establishments like the Chicago Theatre and other fantastic performing venues feature some great acts year-round. This urban hub will keep you busy but gives you a feeling of comfort and ease that not all big cities have. Despite our visit being short, it was enough to know that it was well worth to travel back to one day soon!
Chicago – I hope direct flights from Montreal become more common because a layover in Billy Bishops’ Toronto is lame, to say the least.
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Founder/Editor-in-chief/Creative Director. Passionate about the city of Montreal, discovering its various cultural components as well as exploring foreign places. I am inspired by artists, innovative concepts, philanthropy, creative encounters, and cultural events. View all posts by Anne Jano
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