Five Reasons I Fell in Love with Chicago

In case you couldn’t from my week of posts all about my trip to Chicago — I totally fell in love.

Chicago River & Navy Pier | Our Streamlined Life

The city first came on my radar a few years ago when I started noticing some of my favorite online ladies (Jess Lively, Jessica Murnane, The Everygirl) were all based out of Chicago. Not only did it seem to be a great spot for thriving and aspiring entrepreneurs, but their Instagram pictures were regularly full of gorgeous city views and hunger-inducing food.

“But,” I thought, “Who wants to live in Illinois, anyway?”

I’m not entirely sure what I expected to experience when I got there, but I did not expect to love Chicago as much as I did. I figured it would be a fun weekend getaway; I’d enjoy myself for a few days, then check it off my list and move on.

I guess I should caveat my list below by saying I did visit Chicago in late June — from what I’ve heard, the best possible time to be there. I might be singing a different tune if the city had been in the throes of one of its famously harsh winters.

My sister lives about three hours from Chicago and when I professed my love for the city she looked at me in total disbelief. “We never go to Chicago, if we can help it,” she told me. “If we want to do the city thing, we always go to St. Louis.” Clearly, to each her own.

Ryan and I have shared before that part of our journey is trying to figure out where we want to settle down. And while we haven’t yet answered the question of whether we want to live in the city or the country, if we were to move to a city, Chicago is just the kind of place I can see us heading. Read on for my top five reasons why.

1. Chicago is Full of Urban Parks & Green Spaces

I love the city but I also love nature — making a city full of parks the best of both worlds. (That’s the reason I love Philadelphia and Savannah so much!) I love the feeling of being surrounded by trees, grass, and water, while simultaneously being within walking distance of work, home, and modern conveniences.

Chicago is full of parks, big and small — from Millennium Park to Lincoln Park. In fact, it has more than 8100 acres of green space, with 600 parks and 11 beaches. And the Chicago Riverwalk and the Lakefront Trail make it easy to get close to the water, too.

Chicago River | Our Streamlined Life

2. Chicago is an Active City

Everywhere I went in Chicago I loved seeing all the people out enjoying the beautiful weather, from runners in the park to bikers on the Lakefront Trail. Many cities have a vibe of rush rush rush, everyone hell-bent on getting from point A to point B (and usually wearing headphones to drown out the outside world). In Chicago it seemed like everyone was just happy to be outside … probably a byproduct of those crazy winters!

On a related note, I also appreciated that most of those people who were out and about seemed to be people who lived or worked there. I always find it a little off-putting when I visit a city and find nothing but tourists as far as the eye can see (however hypocritical that might be). Chicago was full of natives out enjoying playdates in the park or a lunchtime run. I love a city that the locals seem to love, too.

Divvy | Our Streamlined Life

3. Chicago is So Clean

If you’ve visited New York, Boston, or Philadelphia in the summer, you’ll appreciate this one: Chicago doesn’t smell like trash. That’s due in large part to its 1900 miles of alleys, which keep garbage and other messy parts of city life out of the main thoroughfare. (This article about this “utilitarian wonder” is super interesting.) It was also the first American city to have a modern sewer system, which probably has something to do with it too.Downtown | Chicago Our Streamlined Life

4. Chicago is Like an East Coast City … but Friendly

Despite the trash comment above, I’m partial to east coast cities like New York, Boston, and Philly — maybe because I’m an Irish girl who loves a good pizza. That said, none of those cities are renowed for their warm, welcoming locals. Chicago had all the feel of an east coast metropolis, but just about everyone we encountered was — wait for it — friendly and helpful. The best way I can think to describe it is an east coast city with a midwest heart. It’s the best of both worlds!

Willis Tower Daniel Burnham | Our Streamlined Life

5. Chicago Has Something For Everyone

Chicago has something for everyone — maybe because it boasts 77 unique and distinct neighborhoods. I hadn’t realized just how big the city is; in my head, I’d always compared it to Boston in size, but at 234 square miles, it’s actually five times Boston’s land area! We spent most of our time in The Loop & River North area, but that’s just scratch on the surface of everything Chicago has to offer. This is a great resource on Chicago’s neighborhoods, and apparently “This Infographic of Chicago Neighborhood Stereotypes Nailed It.”

Read my other posts about Chicago here, here, and here!

I loved Extra Pack of Peanuts’ Destination Diaries – Chicago. Travis is joined by a Chicago native, and he has lots of great recommendations for food and beer. This episode came out right after I got back from Chicago — I think he was there right around the same time I was.

For more ideas on things to do in Chicago, check out our Chicago Pinterest board.

Five Reasons I Fell in Love with Chicago | Our Streamlined Life

I'm the oldest of 12 crazy kids and two pretty awesome parents. My love of travel developed during my early years traveling the globe as an Air Force brat. I'm a runner, a writer, and a reader, and I love cooking up good food and cozying up our camper.

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