North America, Photography

Photo Essay: I’m having a small affair with Chicago

This is part of the #WinosOnTheRoad trip series with Diana of D Travels β€˜Round as we drive across country to start her new chapter in life.

Chicago Theatre

Oh Chicago.

You’re quite the tease.

I always feel like I never have enough time with you and you leave me wanting.

Chicago Skyline

First I went to shoot a short film. I got a taste of you. I didn’t have time to do any city tours in Chicago due to work but I feel like we could have had something special.

The second time I visited you I did so without the love of my life. That’s not fair. He wants to see you too. He has been dreaming about you ever since he played on the Cubs in Little League.

But there is something that keeps me wanting to come back.

Windy City

Is it the unique smell of summer that is like an intoxicating perfume?


Maybe I’m in love with your skyline? Those are some nice lines you have.

Windy City

Or how there are so many things to do and see?


Maybe it is the food? *swoon* Delicious.


…or maybe it is everything.

Windy City

While I don’t intend on moving to Chicago, there really is something special about you.

Windy City

I can’t wait to bring Shaun and fully get to know you.

Until then I’ll continue to visit you in my dreams.

Windy City

Windy City

Windy City


Union Station




Big City

43 thoughts on “Photo Essay: I’m having a small affair with Chicago”

  1. Erica, you need to stop posting about American cities already. You’re making my US itinerary for next year VERY difficult!

    Seriously though, Chicago looks amazing. I always imagined it to be pretty drab and industrial for some reason, so I’m amazed by how glitzy and modern it looks. Great photos πŸ™‚

    1. Tom, and Erica: Chicago is one of the most beautiful cities you can be in. For a real treat look up the history of why there are so many beautiful flowers and pots brimming with plants everywhere. In all seasons. Hang out in the Loop some night after midnight and watch the plant fairies come and water or change plants from season to season overnight…and this happens all over the city. Chicagoland loves to look pretty. Go to Navy Pier in winter and look at the vast expnase of frozen lake. Free trolleys all summer long to almost anywhere including the museum square, where you can meet Sue or spend time discovering other great exhibits. Take an architecture boat trip. The Lincoln Park Zoo is free, and has one of the best ape habitats in the world. I could go on and on.
      BTW, I live in LA πŸ™‚

  2. I just spent a week solo in Chicago and was blown away… The architecture, the food, the parks, the museums, the people, the transportation, the Lake and beaches… This is an amazing, not to be missed city. I loved the energy… Loved it ten times more than NYC!

  3. So I just moved FROM Chi-Town and I miss it more than I think I would miss my big toe…maybe not but I miss it a lot!

    I recommend that next time you go venture out into the neighborhoods, like Lincoln Park and Lakeview. Also order Art’s Pizza. NO they DO NOT have a website I tried to sell them one but got shot down, but now I’m just rambling.

    Old Town is a blast it’s at North and Wells. In fact if you just travel up Clark St you’ll see some great neighborhoods. Also I would eat breakfast at Kanelas at Clark and Belmont. Halstead is another great street to ride the bus up and down. OH and you can’t forget Lincoln Square. It’s farther north but you can ride the Brown Line and get off at Western. Oh gosh I would move back for a freaking nickle!!

  4. Wow, Chicago looks awesome πŸ™‚ Still haven’t even visited the US at all yet – so many places to see there alone! Love the first shot of the theater πŸ™‚

  5. I’ve almost never been to the USA even though I was raised in Canada along the Minnisota US border. This makes me want to start my own love affair. There is SO much to see.

    1. !!!!!!

      The US is so huge. I would be so overwhelmed trying to plan what to see. No matter what you’re going to miss a lot. Hell, we live here and haven’t seen much of it.

  6. I’ve never been there more than a few days myself even when I was going there almost every month for business. I could just never roll it into more than a night or two. I saw more of it in your cool photos than I’ve seen in person. #jealous πŸ˜‰

  7. Ooooh, love the second shot with the amazing cloud detail! Chicago is one of those cities I have spent embarrassingly little time in but am excited to explore more now that I’m just an hour-long, $39 flight from there.

  8. I don’t know why, but Chicago is one of those cities I’ve never had any desire to visit. Probably something to do with the “windy city” nickname, and the fact that I HATE wind. Your photos are really changing my mind, though…

    1. You know, the first time I went I was not that excited because I thought the same thing. Woo. Chicago.

      But then I went and I saw how amazing it was and then it turned into:


  9. Great post! Those pix really show some different aspects of the city. I can tell you that NY is very, very, different. And although it does get windy on the lake, the nickname comes from our politicians, not the weather!

  10. Great pictures of Chicago! Also, I want that mini smores contraption.

    I love Chicago in the summer. The winter? That’s another story…

  11. I have never gone beyond the airport in Chicago. I really want to go and your photos only make this need worse. I love all of the angles of the city you captured.

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