Moving from Indiana to Chicago – Let’s Do This!

So you’ve finally decided to make the big move from Indiana to Chicago. Good for you! I’ve been in your shoes and although it’s an exhilarating feeling to become a part of a new way of life, it’s also pretty darn scary sometimes. So, if you’re feeling a bit intimidated, that’s completely understandable; hopefully I can help a little.

Let’s preface my experience with the fact that I grew up in a small town in Indiana of around 8,000 people. I knew everyone in my class, my high school, their parents, their siblings, their grandparents and their pets. Well, you get it – or even lived it yourself. It was small and comfortable. As I grew older though, my little ol’ home town started to feel small – and a little boring.

From A Small Town To Bloomington, Indiana

So, when I graduated high school, I decided to go to Indiana University and at the time, that town seemed huge to me. When I first moved to Bloomington, I didn’t know one person. I was pretty lost for a long time. But soon enough, I began to know that town almost as well as I’d known my small hometown. I had my go-to spots to watch sports, grab a great local brew, play pool or darts, or eat a great steak.

After a few years, Bloomington began to feel like home. I absolutely loved it there besides the one obvious downfall – it’s a college town and isn’t really a place to start a career. So, I decided to make another big move. That move was to Chicago, and if Bloomington felt big…yikes!

A First Look at Chicago

I was pretty nervous to move again. I’d always wanted to be in a big city but actually making that happen was a bit daunting. I didn’t know anything about the city and I had no idea Chicago was broken up into small little neighborhoods. I didn’t know where any good cafes, restaurants, parks or supermarkets were located. I was pretty lost and really just yearned to have a place that was familiar and felt like home. I really made it a point to explore and find some smaller places that made it feel more homey.

So, here’s a list of some of my favorite places from back home in Indiana and in my new home in Chicago.

My Favorite Back Home in Indiana Sweet Home Chicago
Great Steak Janko’s Little Zagreb RPM Steak House
Sports Bar Nick’s English Hut Public House
Brew Pub Upland Brewing Vice
Pool and Darts The Video Saloon Delilah’s
Local Coffee The PourHouse Cafe Sip Coffee
Best Burger Scotty’s Brewhouse Grange Hall Burger Bar
Late Night Rockit’s Pizza Dublin’s
Music Venue Bluebird Reggie’s

I also had some honorable mentions for Chicago that I just couldn’t leave off the list:

Prime and Provisions– It’s pricey, but worth it. Bordering on River North and The Loop, these guys succeeded at competing with some of the best steakhouses in Chicago.

Headquarter’s Beercade– If you’re looking for free arcade games and lots of them, go to Headquarter’s in River North.

Maude’s Liquor Bar– The West Loop is known for their high quality restaurants and bars, so try everything over there. One of my favorite spots is Maude’s – great food and drinks.

Kirkwood Bar and Grill– It’s a great place to go watch IU basketball or football with fellow Indiana fans. This was my first go-to place. It’s north of the city, but just 2 blocks off the Belmont Red, Purple and Brown line stops.

Finally, there’s Grant Park and Lake Michigan. They are both in the South Loop – right next to each other – so packing up a picnic and relaxing in the park by the lake is a great way to spend a weekend afternoon. I’ve done plenty of those!

All of these places made me (and still make me) feel like I’ve found some of my old small town way of life, mixed with a big city vibe. I know you’ll find your own favorite spots but feel free to borrow mine in the meantime! And if you need help finding an apartment in downtown Chicago, contact me at or give us a try at