Chicago is what Toronto will be like in 100 years – a multicultural city with a beautiful lake view, a thriving art/hipster scene, beautiful architecture … and history (which is why Toronto needs another century to catch up).

It’s about time I went to Chicago! It’s one of the biggest cities and attractions in the US, but I’ve never been interested in visiting many places to the south due to the similar culture and it’s pretty expensive to fly from Toronto to any U.S destination, regardless of our close proximity.
Well, Porter Airlines has changed that with an airport right in the city (Toronto Island) and pretty good seat sales if you’re on the ball.  Plus, having a friend living in Chicago is an added bonus.
Lake Michigan
I do have to say that Porter Airlines exceeded my expectations, with a free lounge for all passengers with Starbucks coffee, non fat chips and cookies! It doesn’t take much to impress me, especially after flying with Canadian airlines that have never attempted such service.
Chicago deep dish pizza

The first thing that sticks out about Chicago is how green the city is. The city is sectioned into distinctly planned neighbourhoods, with tree lined streets, and vintages houses with backyards. I fell in love with the eclectic neighbourhoods, with cute cafes, boutiques and thrift stores. I stayed in Wicker Park, home of the hipsters, with an eastern European history. This area is also filled with art studios – ones you can just walk into, and visit the artist in their realm, where most live, display and sell their work. The Flat Iron Building is known for this, with small galleries and artists’ lofts, giving this neighbourhood an urban hippe vibe (hence the hipsters I suppose).  It’s an art lovers dream!

The Chicago subway system is 24 hours, and simple to navigate. And if you can’t, the Chicago locals are more than happy to help you. You have to leave the American stereotype behind when in Chicago; it has the friendliest people I have ever come across in North America (yes, even nicer than Canadians!).  As most American cities, Chicago also has a big Mexican population contributing to the awesome taco restaurants that fill every corner. But unlike other American cities, Chicago has much MORE than just Mexican food. It thrives as a multicultural city with mostly American and Mexican food choices, but lots of other ethnic hot spots as well.

Chicago and NYC are the biggest cities in the US, so its a basic assumption that these cities are similar, and that they are in regards to architecture, music, sports, shopping, tourism and culture – it is iconic America! However Chicago is much cleaner and the attractions are more accessible. My favourite tourist attraction was the 2 and a half hour segway tour along Lake Michigan. It took us around Grant Park, the aquarium, the planetarium, the soldier stadium, the field museum (infamous for Sue the T-Rex), and Buckhingham fountain. It takes about 30 mins to learn how to operate the segway (much harder than it looks) and the tour was a great way to spend a chilly Saturday.
After the great fire in Chicago, the city became an architectural playground. This is what makes this city unique and beautiful. I can only imagine how much prettier this place is in the summer, a popular venue for open air concerts.
So of course in such a lively city the nightlife would be banging, and that it is! Chicago is THE place to party, with bars and clubs throughout the city. Even though bars close at 2am, the party will continue until 5am in most places. But of course this is the high life where cover and drinks to clubs are expensive and comparable to any big city in the USA. But remember that you can stock up on alcohol at the local pharmacy in the states.
So if you are still wondering if I’m a fan of Chicago then you probably didn’t read this right. Chicago has easily replaced NYC as my favourite American city. I can’t believe I waited so long to visit, but now I have a great little getaway so close to home, yet so different and entertaining.

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