Life Update: I’m Moving to Chicago!


Mitch and I say that we’re moving to Chicago every year. It’s kind of a running joke with our family and friends.

“So, what’s the plan for next year?” they tease, sometime around the spring.

“Moving to Chicago.”

“Sure,” they laugh. “We’ve heard that before.”

The reasons were always there: First of all, it’s the best “halfway point” between our families. It’s a two-hour plane ride to my parents (a local airport is literally five minutes from their house), and it’s a 2.5-hour drive to his parents’ home. Chicago is a gorgeous city, and it’s far more affordable and livable than New York. You also don’t have to live outside of the action to avoid going broke.

We talked—quite extensively—about making the move, but never pulled the trigger. We’d get close, and then quickly get overwhelmed. Relocating would be expensive, time-consuming and draining. And who wanted to ruin the summer with a giant life change? It also never seemed to be the right time. We were either finishing graduate school, getting engaged, or getting married. And then there were my personal issues. I was nervous about leaving my family and friends, and I was desperately attached to New York City.


But Mitch was recently offered an amazing opportunity in Chicago—his dream job, perhaps—and after a long talk, we decided that he should take it. And last weekend, we flew out there and signed a lease for an apartment in Lincoln Park. So this is actually happening. (!)

Needless to say, my head is spinning. Part of me is freaking out—for a variety of reasons. #1? I’m crazily scared to leave my family. The farthest I’ve ever lived from my parents is Fairfield, Connecticut—an hour train ride to the city, and a two-hour drive from their home. I’m super close with them, and can’t imagine life without Father/Daughter Dinner nights in the Financial District with Dad and shopping days in SoHo with Mom. And I can’t imagine not being able to go home on weekends to see my brothers and grandmother. Or not being able to hang out with my cousins, who all just moved to Manhattan!

And then there are my friends. Nearly all of them live in the area. Two of them—Darby and Laura—lived in Chicago for years, but both recently relocated. Darby moved back to the Upper West Side and Laura moved out to Denver. (Just my luck, right?)

And then there’s New York. Oh my goodness. I can’t even tell you how much I love this city. I’ve lived in the Big Apple for eight years, and truthfully, I can’t imagine myself outside of it. It’s my home. It’s where I feel alive. It’s where I grew up, realized the enormity of the world, and fell in love. I adore every neighborhood, every street, and every subway station. Sigh. (More on this later.)


At the same time, though, I’m incredibly excited. While I’ve traveled, the only place I’ve ever lived is the tri-state area. I was signed up to study abroad in London as a college junior, but backed out at the last minute, thinking I’d be too homesick. Am I nervous about being homesick in Chicago? Certainly. But I now have something I didn’t have as a 19-year-old girl: my amazing husband. While I’m far more independent than I was at that age, everything seems a bit less scary with Mitch by my side. (#solucky) In the words of Bono, “a house doesn’t make a home.” We truly have fun together wherever we go.

Which brings me to another point: Mitch. The boy grew up in Lincoln Park! He moved to New York in 2007 to join the New York City Teaching Fellows, and planned on returning to Illinois after he’d completed the program. But then he met me. The guy’s been pining for Chicago—and his family—for so long. (Awwww.) And I love his family. Man. They’re the absolute best. I think of his parents and siblings as being my own, and I’m so thankful to have them in my life. It’ll be so nice having them visit, and visiting them in Central Illinois. My own parents have also promised to come to the Windy City constantly. Like I said, they live five minutes from a local airport, so they can be in Chicago in only a few short hours! Not bad. (Additionally, they always pick up their cell phones. ;))

And my friends? Erica, my BFF, lives in Milwaukee, which is close to Chicago. (Reunited!) And hopefully, others will visit. (Hint, hint.) And I’ll visit them. :) (Love you guys. Don’t forget about me, haha.)

As for my adoration for New York, it’ll be good for me to experience a new place. I love New York more than I could ever express, but it’ll always be there. I’ve also never lived in—or loved—another American city. It’s been a long time since I experienced the exhilaration that comes along with discovering new hotspots and not knowing where I’m going. New York is expensive, too! At times, living here can be fairly difficult, stressful and frustrating. It’ll be nice living in a city where your dollar goes a bit further, and life is a little slower. Doesn’t hurt that Chicago is beautiful, either.


So for now, I’m going to stop analyzing everything that’s going on in my life, and just try to enjoy my last couple of weeks in New York. (Moving date: June 29th!) I know that this is not the most eloquently written post, but my mind is racing. So thanks for listening to me ramble. Stay tuned for many more reflective pieces over the next few weeks.

To new adventures…


  • Kimi

    Wow, that’s so exciting! Congratulations on your new adventure! :)

    xo Kimi

  • Neatly-Packaged

    How exciting!! :) Looking forward to all the awesome Chicago inspired outfits you will come up with :)

  • Kristy

    So excited for you Kelly! Remember, ‘change is good’ and with change comes growth. :) You will make so many wonderful new memories in the windy city and your family and friends will flock to see you and get a taste of all you experience. Can’t wait to read all about your new adventures. So much fun experiencing all that’s new, making new connections and pushing yourself… Have fun with this special time!
    Hugs!!! xo

    • Awww, Kristy–this means so much to me! Thank you! You’re right–change IS good. We’ve been here a while, and it will be exciting to go elsewhere and have a little adventure. But I’m sure going to miss everyone in NYC. Come visit!! Thanks, girl xoxo

      • Aww! You’re so very welcome and sooo sweet! xo

  • Julie Lovenbury

    You’ll get to know the L just as well as the MTA. Chicago is an incredible city, and it’s so beautiful. Summer is hands down the BEST time to be there, so you will be comfortable in no time. Congratulations and enjoy your adventure!

    • Julie, I rode the “L” a couple of weekends ago, and I was absolutely amazed. It’s so CLEAN! And people are QUIET! It reminds me of the Tube. So glad to hear you think summer is such a blast there–I can’t wait! Thanks so much! xx

  • Aww, congratulations to you both – Chicago is such a fun city! Excited to follow along with your new adventure :)

  • Congrats! You’ll fall in love with Chicago. Perhaps not the winters, though. They are much worse than NYC. (More reason to buy cute outerwear!)

    Bedknobs & Baubles

    • Oh my goodness. Tell me about it. I have a puffer coat, so hopefully I’ll be OK, haha! Thanks, girl :) xx

  • Kira R

    Wow so exciting!! Awww we have to make those plans to meet before you go! If you have time that is!! Email me whenever! Chicago is such a gorgeous city!!

    Kira :)

    • Thank you, Kira!! I would LOVE to see you! I’m going to try to clear my schedule next week so I can see people next week! xx

  • Mol C. Nichols

    So happy for you & Mitch! It’s not everyday that someone gets an offer for their dream job. Good luck with the move. Can’t wait to see all your new adventures in Chicago.

    • Awww thank you! I agree–it was something that we couldn’t pass up. On to new adventures! Thank you for the well wishes! xx

  • Congratulations on becoming a Chi-Town resident! So now the big question is – will you be converting to a deep dish family or stay true to your thin crust roots? Chicago really is an amazing city (pizza crust decisions, aside).

    The Salty Hanger

    • Michele,

      Haha! I love it. Okay. So I truly love both. I like thin crust because you can grab it on the go, and walk down the street with it… but I love deep dish, too, as it’s a real meal!!

      So I guess I’ll just have to love both. :) hehe… Thanks, girl! xoxo

  • congrats! i grew up outside of Chicago and it’s such a wonderful city – you’ll love i and New York isn’t going anywhere :)

  • Meagan

    How exciting! Can’t wait to read about all of your adventures!

  • Hunter

    That is so exciting! I’m sure it will be hard to leave NYC, but Chicago is going to be great! I just know it ;)

    Prep on a Budget

  • Alicia

    YOU WILL LOVE CHICAGO! I’m so happy for you, Kelly. I moved to Chicago after college and lived in Lincoln Park throughout my 20s. It’s the most beautiful party of a gorgeous city. We now live on the equally beautiful North Shore. My hubs is a native New Yorker so we still get to NYC often, but both think Chicago is a much nicer place to live. All the best!

    • Alicia, your comment made me so happy! THANK YOU! Ahhhhh—Also so happy to hear that you loved life in Lincoln Park! I am a bit nervous, but I fell head over heels for Lincoln Park when we were recently out there. Maybe sometime we can meet up!! :) xoxo!

  • FatFreeFashion

    So exciting! Congrats! Looking forward to following along with all your new adventures. (kellyintheWINDYcity?) :) Enjoy your last few weeks in NYC!


  • Congrats! Kelly in a different City!

    I’m sure it’s going to be so overwhelming, but I’m sure it will work out for the best.

    Chic on the Cheap

    • Thanks so much, girl! LOVE your post today, by the way! Your photos are always absolutely stunning!!

  • Katherine L.

    Congrats, it sounds so exciting! It’s always fun exploring a new city for the first while too! Can’t wait to read all your posts about it!


  • Congrats on this exciting move! I totally hear you about NYC. Born and bred here myself and living somewhere else makes you homesick (lived in NH and then Boston for six years) but Chicago is such a great city! It’s as close as you can get to NY and definitely more affordable! Just make sure you escape those harsh winters when you can and buy a down parka!!

    • Kate, you’re such a sweetheart! It means a lot to me knowing that others can understand the attachment I have to NYC. You’re right–Chicago IS a great city. And it will be a lot easier. But man. I agree about those winters! Maybe I’ll need TWO parkas ;) xx!

  • McKenna Bass Trahan

    How excited! New adventures await I’m sure! Good luck with the move!

  • Maureen

    Lincoln Park is a nice area. I think you will enjoy yourself. I have lived most of my life in and around the Chicago area. It is beautiful and there is so much to offer.

    • Thanks, Maureen! I agree–I don’t know very much about the area, but it looks fabulous. So awesome that you grew up around there… I hope you’ll share some tips with me. ;)

  • I’m so excited for you! Chicago is a great city and everyone I know loves it! Get ready for the cold; I can’t wait to see your wintry outfits.

    • Thanks, girl! Oh, goodness. I know. I have a pretty warm parka, but I’m seriously considering getting one of those coats that are battery-powered, haha!

  • Congrats! Chicago is amazing, I love that city!

    Eleventh & Sixteenth

  • Joules

    Yay! You’ll love living in Chicago. It’s a great city. It’s good that you’re moving in the summer so you’ll get to see Chicago at its most beautiful!

    Style by Joules

    • Thank you! I agree– Summer in Chicago will be pretty awesome :) Thanks, girl!

  • Nicole Layne

    That is so exciting! I used to living in Chicago and loved it. It is an amazingly liveable, fun city and summer in Chicago is the best! I’m so excited for you!

    to the Nines

  • AvgGirlsGuide

    wow, congrats indeed to new adventures! I’ve been to chicago a few times — my brother lived there — and it’s such a magical, amazing city. So glad you guys can head back there! enjoy the city the next few weeks.


    • Thanks so much, Alyson! You’re so kind. Super excited about the new adventure and next chapter in our lives… :) Loved your post today!

  • Wow, congrats! I knew this was coming eventually, but I was hoping it wouldn’t be so soon. Super excited for you guys, especially Mitch’s job, but sad to see you leave NYC! Hope we can get together before you head out.


    • Awwww thanks, Sam! You’re so sweet! Yeah, I suppose we all knew it was coming… ;) Hope to see you soon!

  • Congrats on your new adventures – it’ll definitely be reminiscent of NYC but in a different way!

    Liz @

  • adoredbyalex

    That’s beyond exciting that you’re taking the jump and following a new adventure! Congrats :)

  • Congrats on a new exciting opportunity! My cousin lives in Chicago and I go an visit every summer (headed there in July) and I absolutely love the city. There is so much to do and see, I have no doubt you will find plenty of success there Kelly!


    • Awww! That’s awesome! I am SO glad to hear that you love it. Makes me even more excited!! Thanks so much, Alex ;)

  • Congratulations! I love Chicago. I’ll be there in August, actually!

    Country Girl’s Daybook: Jesus, Photography, Fashion, & Food

  • I’m so proud and excited for you!!

  • TrendyOnABudget

    congrats kelly! how excited, chicago is such a wonderful city. i’ll have to look you up the next time i am in chi-town! good luck with the move!

    • Yes, you will have to do that! :) I would love to see you!! Thanks, girl!

  • Nikki

    How exciting!! It would be hard to leave NY, but Chicago is so amazing too!! What a awesome opportunity! It was super hard for me to leave my family when we moved 2 years ago.


    • Thanks so much, Nikki! :) New adventures! How is it now? Did you adjust?

  • Congratulations!! That’s so exciting!!

  • Erica Ganong

    I can’t wait for us to be in the same time zone again! You’re amazing! xoxo BFF!

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  • Jeanni

    I’m so excited to follow along on your next adventure. Chicago is the next place I want to live, so I’m eagerly awaiting more Chicago-centric posts. I’ve heard really great things about Lincoln Park.

  • Eva

    I’ve always said Chicago is underestimated and hopefully you’ve already seen enough of him by this day. It’s always good to see positive change! I wish you all the best in future!