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

This is part of the #WinosOnTheRoad trip series with Diana of D Travels ‘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 Responses to “Photo Essay: I’m having a small affair with Chicago”

  1. Waegook Tom July 25, 2012 at 12:25 am #

    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 🙂

    • Sharon Miro July 25, 2012 at 9:12 am #

      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 🙂

      • Erica July 31, 2012 at 12:00 pm #

        Good lord Sharon! Thank you so much for all the great things to do! 😀

    • Erica July 31, 2012 at 12:00 pm #

      Well, you need to be edumacated on how awesome ‘merica is!!!

  2. Eileen July 25, 2012 at 9:20 am #

    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!

    • Erica July 31, 2012 at 12:01 pm #

      Seriously! I love it!

      Although, I admit. I’ve never been to NYC. I’m curious to see the difference.

  3. Arti July 25, 2012 at 9:40 am #

    Those Skyscrapers look daunting! Fabulous captures.

    • Erica July 31, 2012 at 12:01 pm #

      Thank you Arti! They are so high they block out the sun most of the time!

  4. Andi of My Beautiful Adventures July 25, 2012 at 3:23 pm #

    I thought you didn’t like big cities? I loooooved Chicago when we went. These pics are GORGEOUS!!!!

    • Erica July 31, 2012 at 12:07 pm #

      This is my one BIG exception. I love this place!

  5. Leighanna Cumbie July 25, 2012 at 3:45 pm #

    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!!

    • Erica July 31, 2012 at 12:09 pm #

      Well, we plan on going back next summer so I will DEFINITELY use these the next time around!

  6. Irina July 25, 2012 at 4:06 pm #

    What a beautiful collection! I need to make my way there since I’m sooo close!! About 9 hours from Toronto…

    • Erica July 31, 2012 at 12:09 pm #

      Irina! You need to go! 9 hours isn’t bad at all!

  7. Tom July 25, 2012 at 4:10 pm #

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

    • Erica July 31, 2012 at 12:10 pm #

      I haven’t visited most of the eastern US. Like, at all. This road trip was the first time I had been east of Texas.

  8. Diana Edelman July 25, 2012 at 9:12 pm #

    Mmmm Chicago. Beautiful pics. 🙂

  9. mike July 25, 2012 at 11:19 pm #

    It has been awhile since we have visited the windy city. thanks for bringing back some really great memories.

    • Erica July 31, 2012 at 12:10 pm #

      Of course! They already make me want to go back!

  10. Chrystal McKay July 26, 2012 at 7:43 am #

    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.

    • Erica July 31, 2012 at 12:11 pm #


      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.

  11. Mark E Tisdale July 26, 2012 at 10:44 pm #

    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 😉

    • Erica July 31, 2012 at 12:11 pm #

      You need to make sure to take some time out for yourself there. You get to go to a really rad city!

  12. Camels & Chocolate July 29, 2012 at 1:17 pm #

    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.

    • Erica July 31, 2012 at 12:12 pm #

      I have an obsession over cloud porn.

      And seriously – $39? Why aren’t you there NOW?!

  13. Federico July 29, 2012 at 2:38 pm #

    Chicago is my favorite big city in the US, and this is a great photo essay!!

    • Erica July 31, 2012 at 12:12 pm #

      Thank you Fede! So far it tops my list as my fav big city. Heading to NYC soon so we will have to see!

  14. Christy @ Technosyncratic July 30, 2012 at 4:41 pm #

    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…

    • Erica July 31, 2012 at 12:13 pm #

      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:


  15. Escaping Abroad July 30, 2012 at 5:30 pm #

    Awesome pics! Chicago is one of the few U.S. cities I haven’t been to that I’d really like to see.

    • Erica July 31, 2012 at 12:14 pm #

      Do it! Granted, you have to find a good day for weather because it changes so drastically.

  16. Ayngelina July 31, 2012 at 6:18 pm #

    Chicago is so close to Toronto but I haven’t gone yet, these photos make it too tempting not to go soon.

    • Erica August 6, 2012 at 12:21 pm #

      So many Canadians who haven’t gone! Whyyyyy?

  17. Pete August 1, 2012 at 3:40 am #

    Love Chicago! That last photo is my favorite. The mood is so rad!

    • Erica August 6, 2012 at 12:21 pm #

      Thanks! I had a little too much fun with apps.

  18. Fly Girl August 1, 2012 at 9:30 am #

    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!

    • Erica August 6, 2012 at 12:22 pm #

      I’m VERY curious about what NYC is like then. Will me love for Chicago be trumped?

  19. Gina August 1, 2012 at 4:25 pm #

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

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

    • Erica August 6, 2012 at 12:22 pm #

      HA! I keep hearing that. I’m not a fan of cold (which is why we live in Austin) so I’ll make sure to stay far far away.

  20. Suzy August 5, 2012 at 8:23 pm #

    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.

    • Erica August 6, 2012 at 12:23 pm #

      Oh man and the Chicago airports are so daunting! Lady, you need to go!

  21. Sophie September 3, 2012 at 10:05 am #

    That popcorn looks FIT!

    • Erica September 16, 2012 at 11:23 am #

      I was so skeptical at first – especially since it was cheese and caramel but holy crap it was like a party in my mouth. YUM.

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