The Places We Live – Chicago, Illinois

We are spending a long weekend house sitting in a hip condo in Chicago. Our neighborhood alone has enough to keep us busy the whole time, but the L Train is just a block away, connecting us to the entire city. Seems like I better stop writing and start exploring!

20% off annual membership to Use Promo Code RAF69430. The Places We Live is celebrating their 10th house sit!
We just wrapped up our TENTH house sit!!! Celebrate with us by using our code to get 20% off a Trusted House Sitters Membership!

Chicago, Illinois, USA

Illinois is a state in the American Midwest, and is bordered by Wisconsin, Indiana, Kentucky, Missouri, and Iowa, along with Lake Michigan in the northeast and the Mississippi River to the west. For anyone who didn’t grow up in the states, there is a childhood saying that goes “there is no noise in Illinois”. This helps kids remember that Illinois is pronounced without the S (ill-ih-noy).

Chicago, Illinois, USA. The Places We Live. A map of the United States highlighting Illinois along with Idaho (with a heart), California, and New York. A collage shows Chicago Riverwalk, Cloud Gate, and Chicago skyline from the lake.

Thanks to the major bodies of water, Illinois has long been a major population center and has a long, rich history. One archaeological site in west-central Illinois suggests 7,000 years of continuous habitation. Illinois was the 21st state to join the Union and has been home to some of the nation’s most notable presidents, such as Abraham Lincoln and Barack Obama.

The City of Chicago is located in east-central Illinois on Lake Michigan. It is the third largest city in the USA, with a population of over 2.5M people, and hosts the second busiest airport in the world. Some of America’s most famous buildings, museums, and artists are here. Needless to say, we won’t have any shortage of things to do.

Our Neighborhood

We live in the community of Lakeview, an area of Chicago’s north side. The community includes the neighborhoods of Wrigleyville (home of Wrigley Field), Boystown (popular LGBT area), and Belmont Theater District. On top of all of that excitement, Lakeview hosts the annual Chicago Marathon and Chicago Pride Parade. This neighborhood definitely has it going on!

Photo by Blake Guidry on Unsplash

Our street is packed full of trendy shops and restaurants. Like most neighborhoods in the area, there is a strong German presence; for example, the nearby church offers services in English, Spanish, and Deutch. We can see Wrigley Field from the roof of the building, and have easy access to the L Train, connecting us to the city. I would call this prime real estate.

Take a Bacon and Brew Tour in Lakeview and Lincoln Park with Viator

Our Home

Our home is a 1,900 square foot condo on the second floor of a row-house style apartment building. It has three bedrooms, two bathrooms, front and back decks, an open concept living area, and spacious kitchen. There is also a reserved parking area in an alley off the back of the house, which we greatly appreciated, as street parking in the city is either by permit or very costly. Similar condos in the area were sold for $650k and rented for $2,700 per month.

The inside has been meticulously updated and beautifully decorated in a modern style. My favorite spot in the house was the front deck that overlooked the busy street. I really enjoyed sitting out there to watch the world go by. On nice days, people slowly wandered up and down the blocks, stopping into the many shops lining the street or sitting down for a meal at the restaurant across the way. On the rainy days (which were common during our stay), everyone was running from one awning to the next, and surprisingly, laughing along with everyone else playing the same game.

Our Family

Our hosts are from just about everywhere. They moved to Chicago for a job and have been happy with the decision. We had the pleasure of joining them as their guest the evening before they left. We went out for dinner, had an amazing meal, and an even better conversation.

One of our hosts is a social media marketer working for a romance writer. As this seems to be where my career is heading, I took a very keen interest in this. Not only did he have some great advice for my marketing campaigns, but also some really inspiring advice for Josh and his options for self publishing his short story collection, Finding My Voice.

Lucy. House sitting in Chicago, Illinois. Brown, tan, and white dog with long hair sits on a patio chair

Our pet is a dog named Lucy. I love meeting all of these dogs with their unique personalities and quirks. Our previous “Lucy” was a people dog; she would have nothing to do with squirrels or other dogs, but loved other people. On the other hand, our Malaysian princess, Molly, would only socialize with us and other dogs. She wasn’t interested in the kids that wandered the neighborhood, but would instead run for every squirrel, bird, or neighboring pup.  This Lucy, Chicago Lucy, loved everyone and everything.

As a result, taking her on a walk long enough to allow her any exercise is a challenging task. She has to stop and flirt with every passing pedestrian, beg from every diner sitting on the restaurant patios, say hello to every dog barking through their front window, and openly gawk at every rabbit hopping through front gardens (of which there have been a surprising number). I’m pretty sure that, in her mind, everything that moves is a potential tummy rub.

Our Life

Like I said, we have both become truly inspired, and have shifted focus and started some new projects. My goal for this month is to get rejected five times for travel blogging collaborations (getting paid to blog about a company). It may sound strangely negative, but right now I am realizing I’ve been too afraid of failure to even try sometimes. This way, I am at least forcing myself to try — I would rather get five rejections than hear nothing because I didn’t even ask. My other goal is to build up my social media marketing skills. One way I am going to approach this is to start a new marketing support group on Facebook for fiction writers. It will be a good opportunity for me to learn more about the writing “industry” and also flex my tiny marketing muscles to help others succeed.

Josh is also newly engaged, working on a Five Rejection plan for his short story writing. He will be submitting a minimum of five short stories to paying markets (like magazines) this month in hopes of getting published. I can’t believe he is only a few months away from being done with his novel! Because of this, it is time to start building his resume before we shop it around. He is also working on self-publishing a short story collection to be ready in time for the holiday (that’s right friends and family, your darling Josh has the last stocking stuffer you need to win Christmas). We’re new, improved, and ready to roll!


Leave a Comment

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

Create a website or blog at

Up ↑

%d bloggers like this: