That Time I Didn’t See Much of Chicago but Loved it Anyway

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Chicago, United States

Living in Toronto I’m only a short flight to Chicago and despite people raving about the city I’ve never been there.

I’ve heard many times Chicago is the city Toronto could have been if we didn’t ruin our waterfront by slapping a highway between it and the city core and it was the first thing that struck me as I cabbed in from the airport.

A sunny Saturday afternoon people were jogging down paths, cycling with DIVVY bikes and playing beach volleyball and I immediately regretted only flying in for work and not allowing a few days extra to explore.

Mercadito Chicago

But over 4 short days with small glimpses of the city I couldn’t help compare it to Toronto and was envious of the architecture and green space. After renting a boat to tour down the river where we actually drove the boat I decided

I love Chicago

But it’s still feels like an Italian man in a tailored suit. I’ve only admired from afar, made eye contact but never spoken.

But I think we need to change that. Chef Rouge and I have spoken about eating at Alinea, NEXT and wander the neighbourhoods – especially as I’ve heard there is such a large Mexican population, which means more awesome food!

beehive Chicago
Chicago River
Chicago architecture

So it’s sad to walk away from Chicago knowing so little of it but I’m excited to start planning the ultimate food trip in Chicago – better start prepping with some extra gym time and begin researching Chicago food tours.


Join the Conversation

  1. I went to Chicago for the first time in January and loved it! They also have a very large Ecuadorian population (as one taxi driver told me) so there could be some interesting food possibilties there as well! 🙂

  2. Chicago is one of my favourite cities, though I’ve only been there twice. It feels more livable, relaxed and friendly than New York but with just as much going on. Maybe even more with the miles of beaches.

  3. Beautiful photos. On our 6 month road trip around the US, Chicago was the one place we didn’t get to that we really regretted missing.

  4. Nick Paton says:

    I’ve found I can normally tell how much I’m going to like a city from my first 5 minutes getting into the city. Sounds like Chicago might have made an instant impression on you.

  5. Liz Mackenzie-Barrett says:

    Love Chicago.

    Also for an amazing view of the city – go have a late drink at the top the John Hancock building (or whatever it may be called now).

    I was struck by how flat Illinois was and loved all the straight lines of light leading in and out of the city.

  6. Francesca (@WorkMomTravels) says:

    Yes, you definitely need to come back! You’ve made my city look exceptionally beautiful in these photos, too.

  7. Adrienne @ AdrienneAway says:

    Chicago is wonderful, especially in the summer! Shame you didn’t get to see much. Always makes for a great 3 day weekend.

  8. Great photos, Ayngelina! I was just in Chicago for the first time a few weeks ago for a family wedding and really enjoyed the city. I’m a tough Mexican food critic and we had a great meal at a packed taqueria in the leafy suburb of Lisle — that bodes well for the Mexican options in the city 🙂

  9. I also LOVED Chicago! I missed the boat tour, though, so I will have to go back. I didn’t have any Mexican food since we were way too focused on their deep-dish pizza (overrated, if you ask me), but that gives me yet another reason to go back! YAY!

  10. I really need to see more of the US!

  11. It is an amazing city and it has been too long since I’ve visited. Would have loved to do the Bloghouse

  12. Katie @ The World on my Necklace says:

    Definitely one of my favourite North American Cities. I love that there are so many beaches in the city as well as the fantastic food and really friendly people. I hope you make it back there soon

  13. Chicago is so much fun to explore! One of my favorite things to do (if you like looking at fish) is going to the aquarium. Also when looking at different foods to try Gino’s Pizza is a must! Seriously the best deep dish pizza I have had in my entire life. Plus their restaurants let you write and draw pictures all over the walls which is awesome in my opinion 😛

  14. Best holiday destinations says:

    nice place for visit. thanks for posting nice views.

  15. I love Chicago and there are just a lot of beautiful places in that place. Although I’ve been there twice but I feel like I somewhat live their for long already. Chicago is just one of the places that I want to stay and share the beautiful place with my family for a vacation because there are just lot of reasons to love about it. Thanks for sharing!

  16. nice place chicago.

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