5 Years of Living City Savvy

If you had told me five years ago I would live in Chicago, bike commute throughout the city, and have friends in all different neighborhoods of Chicago I would think you were crazy! I took a step of faith to live in Chicago, had a job within a week and an apartment about a month after that. I'm taking you back through all the different lessons the city has taught me - I'd love to hear what Chicago has taught you, too!

Community

You're not alone. When I first moved to the city, I had no idea how people were meeting new friends. Many people suggested different groups in passing like Meet Up, City Socializer, or local Groupon outings but I didn't have the cash flow I needed for some of the activities. I originally moved to be a part of a non-profit but when it disintegrated and everyone moved back to their hometowns, I only knew 2 people in the city. I wasn’t 21, I didn’t know anyone who went to school in the area, and lived so far north no one came to my part of town to hang. I also was so caught up in planning the evening that I never left room for spontaneity, which I think is one of Chicago's biggest strengths!

Re-establishing a friend group took a long time but one thing I’ve learned is to embrace people openly and joyfully. Chicago is full of surprises! I’ve met some of my closest friends on a rooftop party I heard about the morning of. We spent the afternoon exploring and the next few years hanging out. Or maybe you’ll train with a group like when I ran last year’s Chicago Marathon. The experience was stellar, and so were the people I trained with!

Join a non-profit doing something you're passionate about - you're likely to meet someone just as excited as you are volunteering! I've gotten to know many sweet blogger friends by following my passion. Stay true to who you are on social media, you never know who you'll get to know. It might be pure providence and you’ll mesh with the people you work with. It takes time, but the people of Chicago really are friendly and welcoming!

Transportation

I grew up in a normal town in Wisconsin. Not much to write about. So you can imagine my enthusiasm over Metra trains, El trains, city busses that took you anywhere, and the boats that peppered Chicago's water ways. My first apartment was right next to the Red line and I had such an enthusiasm for riding it! Now my favorite is the express bus that takes me downtown in less than 10 minutes but I still have a major crush on the Brown line at night. So peaceful riding the loop and watching all the lights twinkle.

I’ve lived far north, west, and north east. Traveling via CTA is not only time consuming depending on where you are traveling but relying on it in poor weather can be tricky. You really can’t negate the unlimited rides for a month at only $100, though. Summer time Chi is awesome for bike commuters, but I will not bike in the snow. Brr!

I will say, I never thought about distance being an obstacle until living in Chicago. If it’s further than 3 miles away, I’m re-thinking if I’m going. A great solution for me: I’ve started to mark different places in neighborhoods I want to explore and block out some extra time when I’m near the area to actually visit. Google Maps folders is your best friend! If you're looking to learn new neighborhoods, follow a few as many Chicago publications on Facebook and watch their events page. I follow Timeout, DO312, Chicago Bucket List, and Choose Chicago. The more events you go to, the more event planners have your email and you'll start getting more invites. Or just watch local Chicago bloggers' Instastories. Would it even be a big city if it wasn't all about who you know?

Style V.S. Function

Have you ever planned an extraordinary outfit to go with an extraordinary day? The first time I visited Chicago, it was my 18th birthday, In March, and 30 degrees outside. I had a "spring" (summer) dress in mind that I was determined to pair with a jean jacket and riding boots. But I didn’t have riding boots so I wore sandals. In 30 degree weather. In Chicago. I was a popsicle by the end of the day and terribly sick the rest of the weekend. This was the first lesson I learned but it was far from the last of my style fumbles.

Style functionality is a painful lesson to learn the hard way. I LOVE heels and I hardly ever dress for the weather. If I am inspired by an outfit idea, I want to wear it immediately. When I first moved to the city I’d wear 6 inch heels and walk to the el, walk half a mile to an event, and stay standing most of the evening. I was always in crippling pain the next day. Never one to compromise on style, I resolved to find a solution so I didn’t have to limp the night away.

If you’re visiting Chicago, plan for the weather! If you live in the city and you have a long day of fun, plan for cute shoes and walking shoes. Often, I’ll wear walking shoes to the event, change and wear my evening shoes until it’s time to go home. This keeps my blisters from overtaking my feet and a smile on my face. You don’t have to suffer for style!

Weather

Chicago’s weather feels like it changes every hour. I once had a sunset sail planned for a friend visiting out of town but the water was too choppy from the wind and they had to cancel. It was a beautiful day - just too windy in the evening! Ugh! The next day it was supposed to rain but never did so it became the perfect beach day. Just like you never know what adventures your day in Chicago holds, you never really know what the weather has in store for you either.

You also have to choose if you're dressing for indoors or outdoors! So many girls leave their coats at home because they're going to the club and don't want to check a coat. I know, I know, why not just keep it in your car? Not that simple since very few of us own cars now. Still, always come prepared because you never know where the night will take you..but we already covered that!

There are so many great outdoor spaces in Chicago to explore and the amount of indoor entertainment is teaming as well! Museums, parks, theaters, and of course: shops and restaurants.

Punctuality

It’s a fluid thing in the city. My first job here was flexible when I began to learn the struggle of public transit and if it’s a party, most start times are a suggestion. If it’s a real shindig, everyone is going to show up at least an hour after it starts. However, I’ve hosted a few parties and gambled on the last part. Always be ready 15 minutes before guests are to arrive! I learned the hard way and had to keep a few guests waiting as I scrambled to change from cleaning to clothes to party attire. Whoops!

Transient City Living

People come and they go. Like my previous experience with the non-profit, some people are only in Chicago for a short time. The beauty of the city is that it offers so many learning experiences and allows for you to transition from one passion to another so quickly! It’s hard to say goodbye to friends but it’s so easy to fly out or take a train from our different airports and train stations, there's hardly a reason to complain.

Best For Last

Chicago taught me to dream bigger and lay down insecurity because everyone battles it. Chicago taught me to embrace other ways of thinking that were not similar to my own and ask questions not to prove others wrong - but to learn and eventually understand. Chicago taught me that you’re only as strong as your greatest weakness and to not shy away from trying to challenge and overcome your fears. Chicago taught me finding authentic community is hard but when you have it, be ready for the night to take you to some crazy places. Chicago started as something so big and impossible. It was a faith journey to get here and there’s days where it is still a faith journey to live here. But more importantly, Chicago helped me find myself. I'm really grateful for the people I've met along the way and the memories we've made. Here's to the next year of memory-making!