Coming Back to the City Where You Used To Live

As a teenager growing up in suburban Michigan, I dreamed of escaping the endless strip malls and leafy green streets of Midwestern suburbia. So the moment I graduated from high school, I headed straight for the nearest metropolis- Chicago.What to do in Chicago And there I lived for four freezing-cold years of wild St. Patrick’s days and lazy Sunday morning brunches. Until I left after graduation to move to Paris.

Coming back a year later, I realize that not much has changed. It’s still so swelteringly hot in the summer that the trash stinks. The brown line still creaks as it rattles along and the 312 beer tastes just as cold and tasty as I remembered. My good friends in the city still cook gourmet food out on their patios and are always sweet enough to invite me.

But a part of me feels guilty for moving away and sacrificing the closeness of my college friendships. It makes me sad to know I’ll miss out on all the little things: the last-minute indie concerts, the Friday night wine tastings, the cheese curd-filled ski trips to Wisconsin. And gradually I fear our closeness will wane, and all those friendships I spent four years forming will cease to be.

The reason I don’t live in Chicago comes down to the fact that I want to be somewhere where everything’s new, where I can really grow. And having grown up in the Midwest, Chicago just doesn’t feel different enough. Everything is familiar to me in Chicago- from the nasal Midwestern accent to the oak trees lining the sidewalks to the way people say “pop” instead of “soda.” And after four years of living there, I know the city like the back of my hand.

But among the familiar, there were new experiences. 

Like the cupcake ATM at Sprinkles, which distributes delicious cupcakes 24 hours a day. (THANK GOD that when I lived a few blocks away this did not exist.)

What to do in Chicago

And the $18 view from the top of the John Hancock Center which I had never seen before. (Why is it that when you live in city you never do the touristy stuff?)

What to do in Chicago

What to do in Chicago

And the Mystic Blue dinner cruise I took with my good friend, Victoria, which provided panoramic views of the city and lots of on-board dancing. (Said cruise will forever be remembered as that one time when we crashed an Israeli wedding on a boat. No, seriously.)

What to do in Chicago

What to do in Chicago

What to do in Chicago

What to do in Chicago

But on my return to Chicago, there wasn’t just the new- I also made time to revisit my old favorites as well.

Like brunch at my favorite breakfast place in Lincoln Park, with jars of Nutella on the tables.

What to do in Chicago

Brunch is hands-down the best thing about being back in America.

And wandering Old Town, stopping for my foodie favorites- a.k.a. frozen yogurt at Pinkberry and spices at the fragrant Spice House.

What to do in Chicago

What to do in Chicago

Overall my visit to Chicago made me realize that despite missing so many of my great friends who live in the city, and despite all of the incredible food and architecture the city has to offer, I don’t want to live there again but will always love to visit. Coming back will always remind me of a very happy time in my life, and I’ll (hopefully) always have a friend’s dinner party to crash.

 Have you ever gone back to the place you used to live?

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Many thanks to Mystic Blue Cruises for hosting me on their dinner cruise. They in no way insisted that I write a favorable review or that I crash a super-fun Israeli wedding.

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About Ashley Fleckenstein

Ashley is a travel and lifestyle blogger who lives in Ann Arbor, Michigan. Since college she has au paired in Paris, backpacked the world solo, and lived in Uganda. Her work has been featured by Buzzfeed, Forbes, TripAdvisor, and Glamour Magazine.

14 thoughts on “Coming Back to the City Where You Used To Live”

  1. When I came home from Paris I was worried friendships would be changed, like you! Nothing had honestly changed though, the way I looked at it was that if I could not remain friends with someone after moving abroad, we can’t have been that close in the first place! I also did notice that within 2 weeks of being home I already wanted to be back in Europe again… Hahaha, hence why I’m going back now :) Great photos! x

    • It’s so true- your good friends will be waiting for you when you get back! And honestly I’m feeling the itch to travel again as well, and now know that I hope to live long-term in Europe again someday.

  2. Looking stunning – you and the city both ! I feel very similar to every time I go to Houston – nothing changes, which is comforting but boring. However, it will always be home, and those friendships are still some of my strongest, in major thanks to Gchat and WhatsApp.

  3. Yes, it really is true that you can’t go home again. Chicago is an amazing city and while it’s good you had those experiences living there there’s nothing wrong with moving on to a new place and only returning to visit friends. It can make the city even more enjoyable to get away from it and return as a visitor.

    • So true, Lance. I definitely enjoy Chicago more now that I don’t live there because now I try to squeeze so many of my favorite things and favorite people into only a few days. It’s a lot of fun to visit but the winters will keep me away!

  4. I’ve lived in the Chicagoland area for most of my life and haven’t done most of the overpriced touristy things, heh. I haven’t even been to most museums since elementary school (for field trips), I’d like to find time to utilize an “Illinois Resident Discount Day” at the Shedd. I imagine I’ll finally visit the Sears/Willis Tower once I permanently move away and come back for a vacation with a significant other.

    Regarding friendships, I feel like most friends tend to drift apart at least somewhat. Even if you didn’t move away, just the hustle and bustle of “real life” would add some distance to your relationships, regardless of whether or not you all stayed in Chicago.

    • I know what you mean- a lot of the Chicago attractions are quite pricey! I guess when you live there you think you have all the time in the world to see the attractions, but now when I visit I’m often showing foreign friends around who are more interested in seeing things like that :)

  5. I know exactly how you feel: My current summer job is in the city where I did my undergrad and where I had some of my best years as a young student. Being back there somehow it feels like I never left, but I also know that it will never be the same again…
    Chicago looks amazing though! That photo of you is gorgeous!

  6. I’m so glad to hear that you had a nice trip home!

    I am currently struggling with planning a trip back home. It’s only going to be one week and I am already dreading it. :( I am now 5 years out of college and about 90% of my good college friends no longer live in Atlanta (my “hometown”). So going back is plagued with determining where I can stay and how to get around… I’m sure I’m being pessimistic for nothing, it’s just hard to go back and expect to meet up with old friends right where we left off, knowing now that so much has changed in our lives (not only physically from maybe marriage or new babies, but also mentally in terms of my changing views and theirs, which have stayed the same).

    Wish me luck! :)

    • That sounds really tough but I’m sure you’ll work it out! It’s really hard when you have completely different viewpoints on how life should be lived from your friends, and it can cause you to grow apart.

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