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Big City Christmas (One of My Most Favorite Trips Ever)

 Disclaimer: This is a long post. A lot of pictures, a lot of story, a very special trip I’m aching to write about and want to remember. I was going to break it up into a couple of posts and be brief because any guide to “successful blogging” will tell you that. But this one’s for me. Feel free to scroll through quickly and wait for another brief post. Or stay. Bundle up. And come along for a story about a holiday wonderland.

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When I was a teenager and my dad came back into my life after many years of being separated, he and Gary took me to Chicago the weekend before Christmas as an early birthday present. We walked the snowy streets together, visited the top of the Sears tower, stood in long lines just to get our hands on hot Garrett popcorn, and huddled up in window seats of little restaurants at night to watch the lights and scenes at dinner. It was magic. We stayed on a high floor in an old hotel–a budget deal but charming, nonetheless–and on our last night there, I climbed up above the heater into the narrow window ledge overlooking the city lights and wrote in my journal about every sight and sound and feeling I experienced that weekend. I remember my dad waking up to find me in the window.

“Aren’t you going to go to bed?” he asked.

“I don’t want it to end,” I answered, a story he now retells when mocking my tendency to go overboard on “seize the day.” For the record, I’m learning the balance of “seize the day” and “end it while it’s good”.

That weekend started a tradition of many trips that followed and planted a seed of an appreciation for Chicago at Christmas that would grow into what it is today–a full blown love affair. My last December trip there was when Brett and I were dating. We went ice skating, drank hot chocolate, took lots of snowy pictures and feck yeah, I came home and spent three hours scrap booking all the memories with overpriced glitter stickers that said dorky things like “Baby, It’s Cold Outside” and “Bundle Up.”

Think I’m joking? Look. I found them.

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By the way, I don’t bullshit about important things like scrap booking. I’d also like to note my appreciation for the fact that I took the time to double mount some typed print that said “ICE SKATING” and stick it next to the ice skating pic, lest you not realize that two people with skates on their feet gliding on an ice rink are “ICE SKATING.” I was a very thorough scrap booker, okay?

In the midst of all that holiday magic over the years in that city, I remember one recurring thought, especially watching little girls all bundled up, walking out of American Girl, cradling new dolls*: I can’t wait to be a mom, and I can’t wait to bring my kids here someday at Christmas.

(*Motherhood is not a snow globe scene where everything is so dreamy. But sometimes it is.)

Fast forward to three weeks ago. My sister texted me and my dad that she was going to be in Chicago the weekend of 17th. “I wish so bad we could all be there.”

On a whim, I checked Expedia and there, as if she was waiting for me to come back to her all this time, was Chicago in all her glory, manifested in a crazy cheap ticket price that was practically begging me to book it. Mind you, it was Spirit Bare Fare which is like booking some folding chair seats duct taped to the back of the plane and paying extra per ounce of clothing you’re wearing, but whatever. I would agree to being duct taped–naked–to the outside of the plane to go to Chicago in December.

I asked Brett to go, but he checked the weather and said, “F@#k no. See if your dad wants to go.” Also he had to work.

I had three weeks to plan a 2-day trip to the tundra. Fortunately, we have a lot of clothes for cold weather. I’ve saved everything we’ve bought for a few trips to Michigan when Lainey was little and have picked up a couple more coats from thrift shops, always in the hopes that we’d have another trip someday and I’d be able to say, “Thank God I bought those coats.” As soon as I booked the tickets, I bought some yarn and crocheted each of the kids a scarf for the trip because it’s the only crocheting I know how to do (straight lines!), and I don’t often get the opportunity to pretend I’m a real crocheter.  Also, when my friend in Chicago heard we were coming, she pulled more boots, coats and snow pants, covering every size because she has 4 kids and a lot of hand-me-downs. She also invited us to stay in her city apartment which turned out to be magic. MAGIC, I tell you. As if Kathleen Kelly herself turned over her keys.

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Of course, once we got to Chicago, I wanted to do it ALL. I knew I’d have to pare down my list and enjoy being together more than going, doing, seeing, but I also wanted the kids to experience a nice “sampler platter” of Chicago at Christmas.

My lofty list I knew we’d have to cut down looked like:

  • Ice Skating and Hot Cocoa in Millenium Park
  • Carriage Ride by Water Tower
  • Top of John Hancock Building
  • State Street Macy’s Window Displays
  • Christkindlmarket 
  • Garrett Popcorn
  • Deep Dish Pizza (Lou Malnati’s or Giordano’s)
  • Train Ride (there’s also the Polar Express train that leaves from Union Station, but it was all booked up long ago)
  • See decorations in The Drake Hotel or The Peninsula
  • The American Girl Store

I bought tickets online to 360 Chicago (at the top of John Hancock Building), and then left everything else wide open.  I knew it was going to be exceptionally cold, and if we needed to spend most of the weekend huddled somewhere inside, watching it snow from the windows, so be it.

I waited until last minute to surprise the kids. They thought they were headed to school Friday morning. Instead, I told them suitcases were packed and in the car–we were on our way to pick up Poppa, grab breakfast and head to the airport.

The rest was MAGIC. And by magic I mean, of course, with all the expected hassles of taking three kids–one of whom’s name rhymes with CRASH–to a cold big city. Hassles included fits from fingers not going in the right glove holes, not being able to play in the rotating doors for as long as you want, getting help walking across a crazy busy street when you wanted to wander across yourself, not getting to push all the buttons on the elevator and being told you cant get on the escalator backwards. There. I think that about covers it all.

Flight attendants, prepare for takeoff.

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I’m sure all the passengers between Dash’s seat (with my dad) and ours appreciated Dash’s constant whack-a-mole pop-ups. “MOM! MOM! MOM!” (insert smile and wave).

A,4.

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Part of the fun of surprising them was packing an epic travel backpack with a couple new travel games, crayons, books and favorite snacks. We played these games all weekend.

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And then, as we started to descend, you could see it in the window…snow. Piled on rooftops, blanketing fields. We were not cool and calm about it at all. My dad actually pulled out his bluetooth speaker and played White Christmas’ “Snow” for a 19 row stretch of passengers to hear, and it didn’t embarrass me one bit. In fact, I could not stop smiling.

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And when the taxi approaches the city and you can finally see that beautiful skyline? I get butterflies in my stomach for just a tiny second. There she is, the beauty.

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We barely settled in on the first day and as the sun set, it happened…thick flakes started falling fast. “I can’t believe this is happening,” I told my dad.

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One of my very favorite moments from the trip: When the kids were all jammied up, I decided to venture out in the cold to the market to get a few things. Lainey saw me bundling up and asked if she could come too. “It’s going to be super cold, are you sure?”

“I’m positive.”

We walked in the snow–just me and her, stopping so she could kneel down, take her gloves off and feel the snow in her hands. She didn’t complain about the cold once, and I swear under those corner lights, with that snow falling and catching in her hair, with the city swirling around her, she looked prettier than she’s ever looked.

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We walked slow and pointed out every Christmas tree visible from apartment windows. From one window, you could see a whole mess of people laughing.

“Look, Lainey! A Christmas party!”

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We caught snowflakes on our tongue. We slid our boots on slippery spots to pretend we were skating. We bought milk and wine and juice at the most charming market that was, of course, playing the best Christmas music. And then she looked up at me in that snow storm and said, “I feel like we’re in a Christmas movie, Mom,” and I knew I’d remember that moment forever.

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As for Poppa and the littles, turns out they didn’t need the milk and wine.

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This window was definitely a favorite spot.

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And the stoop. It couldn’t have been more picturesque–snow lightly dusted in all the right spots. I mean, come on.

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(This little hat has always been a favorite since Dash wore it as a baby on a trip to Syracuse. We dropped it in Macy’s on the last day, though, and never found it, so boo.)

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Nella took a particular liking to “the man”.

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The city waking up…

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(Big City Rule #124: Visit a church. At least one.)

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Dash would have wandered that city all by himself, no problem, if we let him. He didn’t want to hold hands, he wasn’t overstimulated, he seemed to know where he was going, he owned it. He Kevin McCallistered those streets like it was his job.

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You’re THREE, Dash.

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A definite favorite of the trip: 360 Chicago, the observatory at the top of the John Hancock Building. We were at the door when they opened and for a good hour, there was hardly anyone there but us. There was something so special about nearly having the place to ourselves; being warm, looking out at the city on such a cold day; the Christmas music playing overhead amid the quiet of the scene.

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There’s a little cafe in the corner overlooking Lake Michigan (the entire floor is windows). I was playing with the kids in another corner when my dad hollered, “Kelle! Come here! I got us coffees! With WHISKEY!” And so I ran.

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Tissue please.

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The kids didn’t want to leave, so we just hung out at the top of the city, doing puzzles, drinking coffee and eventually running around and wrestling on the floor (Brett would die).

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I did brave the Tilt experience as well, a set of windows that you position yourself in and then get tilted over the city for downward views. Sweaty palms, man. But I did it.

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American Girl Store. Rite of passage in the city and so much fun, but LORD were there ever a lot of people in there. A lot of bored dads huddling by the doors too.

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For the record, Dash is not taking money in this photo, but putting some in. I clarify because the former was the case with him once.

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We wanted the kids to experience the train. They loved it so much, we sat and relaxed on it, taking it outside the city and then back in, just for fun.

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When in Rome. Giordanos, baby.

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My sister and my cousin–another favorite moment. We had drinks at The Peninsula, and the Christmas vibe was ON POINT. Total Christmas Party Hop.

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The walk back to the apartment that night was so enchanting. Snow falling, people huddled behind windows of cozy taverns in early holiday celebrations. Christmas lights, evergreen garlands, horse and carriages taking night owls back to the their hotels. My sentimental heart beats wildly.

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Our last day…up early so we could drink it all in before we left.

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Nella loved being able to see her breath.

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We spent the last day in the theater district, mainly at Macy’s because it is Christmas wonderland, and the kids didn’t want to leave.

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(Dash is obsessed with my sister. Obsessed, I tell you.)

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There are 8 floors, all connected with escalators that the kids wanted to ride repeatedly. Each floor highlights something different–Santa on 6, Holiday Lane on 7 and The Walnut Room (world famous Chicago restaurant–since 1907!) and the best view to an epic Christmas tree on 8. Holiday Lane was my favorite. That scene in Elf when Buddy stays up all night and creates a Christmas wonderland in the store? This is the store. Holiday Lane is his masterpiece.

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(8th floor tree view, looking down on The Walnut Room.)

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And the window displays. Add Chicago Macy’s Christmas Window Display Decorator to the jobs I’d like to have someday (along with “The Christmas Heloise” Tip Columnist for Village Gazette of a small Stars Hollow-ish town, Hospital Nursery Baby Rocker and Sherwin Williams’ Paint Color Name Colorer).

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Here’s what I have to tell you: Want to do something special with your family next Christmas? Chicago. Even if it’s freezing.

It was magic, a moment in motherhood for me that I will always remember, when all three of my kids were still enraptured by all the imaginative delights of Christmas. When the inconvenience of cold couldn’t hold a flame to the wonder this city offered. When this one could still sit comfortably on my hip and shield her face from the cold in my scarf.

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The last stoop pic before climbing in our Uber to the airport. Dash cried, “But I don’t want to go home.”

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Happy to be warm and home, looking forward to the wonder this week holds, and remembering all the memories.

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And a crappily filmed video (I didn’t video a lot, but there was enough to stash this in our memory archives).

chicago best from ETST on Vimeo.

Now if only we can convince Brett that the cold is worth it to do this trip again someday. After seeing the pictures and hearing our stories, he says “Maybe.” HOPE!

Comments

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  1. Love it! I live in Australia so can’t imagine a white christmas. Your dad with the Christmas music on Landing is so awesome. I particularly loved your walk down “scrap book memory lane”. Have a great Christmas xx Kelly

  2. Love it all! I lived in Chicago for 10 years. We now live in Michigan but my parents live in the northwest suburbs. You’ve totally inspired me to take my kids next year. You’re so right..it’s a magical city during the holidays. Thanks for sharing all your memories and pictures. Merriest of Christmases to you!

  3. I have loved following your trip on IG:)
    I bet your dad is recuperating:)After having adored every precious moment.

  4. Well I bundled up and stuck around to read the whole thing and enjoy each beautiful picture. Your trip looked amazing. And tundra it is here. I live about 1 1/2 hours from Chicago. Your trip to Chicago, reminds me so much of my few and far between trips to Florida. The sand, tree’s and water are so incredibly amazing to me, like the snow was for your kids. Love that they could experience it. But because I live here, and am either ready for it to be over, or ready to visit your sunshine state, I have to also agree with Brett’s, “F@#k no” response as well. :-)

  5. I have never loved a post more! I felt like I was there. Merry Christmas Hampton Family!

  6. Loved seeing all the pictures! And loved your storytelling, as usual. We are taking my 10 year old to Chicago next week- now I am even more excited!

  7. My son is in his twenties now, but the memories of saying, “You are three!” and for so many years after. I would do it all again.

  8. Beautiful post, gorgeous images. Thank you for sharing the magic and spreading the cheer. Merry Christmas!

  9. I too have a love affair with Chicago (especially at Christmas), and you just brought it back to life with your beautifully-written post. Merry Christmas!

  10. Hi Kelle, I’ve been following your blog for years, and this post is one of my favorites. Your heart is so transparent in joy, and you do such a good job adding the little extra it takes to really make experiences memorable – not to mention just getting out there and doing it! I got teary eyed reading about your dad pulling out the speaker on the airplane, and my heart loves what this trip meant to each of you. Thank you for your willingness to share, your zest for life is inspiring. :)

  11. Kelle,

    All of your posts, but especially this one, really struck a cord with me. A cord that produces big, fat tears because you are sharing something so special with your kids and seem to understand how fleeting and cherished it all should be.

    For me and for many, the holidays are difficult because of the loss of loved ones, family tragedy, etc. I am looking forward to Christmases with my future children, where things are infinitely more special.

    Wishing you and yours a lovely holiday. And thank you for sharing your life with us.

  12. And here I thought you were going to Michigan. HA!!

    Looks wonderful and oh what memories.

  13. i need to go to chicago STAT – amazing. merry christmas!!

  14. I vote for more LONG POSTS !!

  15. Just perfect–thank you!

  16. I love this! We lived in Chicago for 7 years and after reading this I so want to plan a trip back there with my children next year at Christmas time! Thank you for inspiring me:-)

  17. Hi Kelle! I absolutely loved this post. I live in Chicagoland and share a love for all the same holiday sights and scenes that you love. I’m heading into the city later tonight, actually! I wanted to ask you, do you mind sharing where you got that toy camera that Nella has in one of the photos? I’d love to get one for my daughter!

  18. Laura Ortiz says:

    Love your story about Chicago, I felt the same way a year ago when I took my kids to Philadelphia in December,
    Elfreth’s alley and the historic district will be in my memory forever.
    Thank you for sharing.

  19. I LOVE this!! We took a family vacation to Chicago this summer so it was the exact opposite season…it’s so fun to relieve our trip and some of the favorite places we went, but covered in white. Wonderful pictures!!

  20. Oh My Goodness! Sooo want to go to Chicago now! That pub looks like the one in About Last Night with Demi Moore and Rob Lowe. Yet another reason to go!

  21. I loved reading about and looking at the pictures of your weekend. We took our kids (10 and 7) to New York City a couple of weeks ago – It was equally as magical except no snow :( And definitely not enough time. We did a lot of the big things (Radio City, Empire State Building, Santa at Macys, carriage ride in Central Park, Rockefeller Center, Christmas Windows), but it was a little too rushed (and NYC always feels rushed!) I definitely want to go down there another year in the not too distant future and just soak it all in without all the big ticket items.

    Merry Christmas!

  22. It is fun seeing Chicago through a different lens. I look at your kids swimming in the pool in December, and that looks magical to me! We live in the suburbs and it’s all boots, and hats, and gloves lately! Glad you enjoyed yourselves here.
    Merry Christmas!!

  23. Carrie davis says:

    You Kelly, make me smile with your story. Knowing how to enjoy the art of playing with your family and creating memories. I now have momentum to create something new this holiday with mine.

    Merry Christmas!

  24. Christmas is my absolute favorite time to visit Chicago. I live in the Chicago suburbs and it NEVER loses it’s magic. You captured it beautifully and made me tear up as I have a new baby and CANT WAIT to make memories with my little one downtown. We braved a snow storm the weekend before just so he could get a picture with Santa at Macy’s. Totally worth it! Thank you for your beautiful post that memories trump weather any old day!!

  25. I do love your post! It was like been there with you! Especially I loved your pictures, can I ask you which lens did you use? Thank you and marry xmas (from cold Milano-Italy)

  26. This made me cry. Magical.

  27. Krystal Verstraete says:

    This tugged at my heart-strings. We’ve been living in Malaysia for 3 years now and I really miss home (Chicago), especially during this time of year. Thank you for capturing the magic of Chicago at Christmas! I’m keeping this blog forever and planning the same weekend the first winter we’re back! Thank you.

  28. Margaret kirkpatrick says:

    Such fun! Chicago is a favourite city of mine too. I must go around Christmas some day!

  29. Thanks to this post, I’ve added “holiday trip to Chicago” to my ever-expanding list of stuff to do with my kids before they’re grown. In related news, I’ve made “rock parenting like Kelle Hampton” my New Year’s resolution for 2017.

  30. I grew up in and around Chicago. My Dad used to take my brother and I downtown every Christmas from the time we were old enough to hold on to his hand I think. I love seeing the windows at Marshall Fields (Macy’s now), riding the train into the city, visiting the Chicago Tribune where he worked, eating at the restaurant owned by a friend of his and ordering a Shirley Temple LOL. We I’ve in Texas now, but I’ll always treasure those trips downtown.

  31. Heaven on earth! Thank you!

  32. I am not going to lie… I LOVED the long post! Snuggled up with some hot cider and my heated blanket (to pretend its not swinter (sunny/winter=swinter) weather here in AZ and I am reminiscing on my journey living in Chicago! Its been 5 years since my 27 year old self lived there and I miss it soo much! Living in the PT towers (the 4 identical towers you can’t miss em) downtown was so magical and just blocks away from all the magic! Thank you for giving me a walk down memory lane for myself and sharing your experience in one of my favorite places! Sending love light and more good cheer to my favorite blogger! PS I wouldn’t be mad if you wrote more long blog posts in the future. I truly enjoy them!

  33. I miss your longer posts like this! i love your writing, it’s my favorite. You should do it more. When I first found you (right after Nella was born, but before evvvveeryone else found you), I went back and read ever single post you’d ever written. This reminds me of those posts. A little deeper, maybe? Whatever it is, I love it. Also, I loved the old pics of you and Brett!

    XOXO,
    Angie from Ohio

  34. Thanks for sharing! This was super sweet and your post was definitely not too long. It’s easy to get caught up in the stress and chaos during this time of year and this post was a great reminder to enjoy the sights and sounds. I totally felt your holiday spirit in this post and helped boost mine today! xo xo

  35. Enchanting! This whole post is magical. <3 Your pictures are amazing. Merry Christmas!!

  36. Where did you stay? I love the old character of it.

  37. I’ve followed your blog for year…and I cried reading this entry! My children are all adults now…but we took two trips to NYC when they were little at Christmastime…such great memories…I’m going to look for the pictures now!
    Thank you…and have a blessed Christmas!

  38. Donna Owens says:

    What a post! Our son lives in Chicago and we were there to see Adele in July, but there is truly something amazing about Chicago at Christmas. Next year, I am going in December. Oh…and I want to live in your friend’s beautiful place! It looks like a movie set! Merry Christmas!

  39. Thank you so much Kelle for your posts and this one particulary ! I believed I was with you at CHICAGO ! Excuse my mistakes , i ‘m french and forgot my english’lessons !!! I wish you and your family a sweet Christmas

  40. lovely moments of Christmas baby…@@

  41. We do our Christmas trip to NYC. I’ve tried (and tried!) to be a Chicago fan, but I’m just not feeling it…

    Love the pics and stories – and yeah, I read it ALL! With a cup-o-coffee.

  42. These pictures are absolutely breathtaking. I always love your photographs and storytelling. You seriously inspire me to capture the everyday in such a beautiful way

  43. Chicago at Christmas could mean a visit to the Home Alone house, right? Maybe add that to the next trip’s bucket list!
    http://www.zillow.com/homedetails/671-Lincoln-Ave-Winnetka-IL-60093/3360197_zpid/

  44. Gretchen in oregon says:

    Long time fan here… this may be your best post ever! My favorite part was your precious Lainey Love braving the snowstorm with you and telling you it felt like she was in a Christmas movie! Beautiful mom, beautiful children, beautiful trip, magical Poppa! Thank you for sharing your amazing trip with us, for people like me who can no longer travel. There is no better time than now to create memories… may you and yours have a wonderful Christmas together. God bless… xoxo
    P.S. Your story ended too soon for me Kelle! Brett… please take Kelli back to Chicago at Christmas time next year!

  45. Nicole Sponseller says:

    Kelle, I love this. These pictures are inspiring me to tote along my Nikon more often but my 35mm and my 50mm are too hard to use in tight spaces. My 18-200mm is too heavy and makes me feel like paparazzi. Lol. Can you recommend a good lens for “all the time” use like what you use. I think you’re a Canon girl, but I’m sure Nikon will have something comparable. You make Chicago look dreamy! -Nicole :)

    • Nicole! (smiling, waving ;o) I love my 16-24. A little more wide angle, so those tight, sharp portrait shots aren’t as good, but for traveling and background scenes and getting the whole feeling in a shot, it’s a great lens and not near as bulky and heavy as the 200. A 50 is not so tight and close on a full frame, too.

  46. It makes me sad that Brett missed this great family memory. Heidi and your dad get so many of the magic trip memories.

    • Thanks for your comment, Paula. Another way to look it is how great that our kids get to experience magic trip memories at all and with wonderful friends and grandparents! Our family isn’t sad about it. :o) I’m happy to have a husband who may not love to travel or be able to as much as I do, but makes the travel memories we do have wonderful, home memories even better and supports and celebrates the trips we do take without him. And we’re thankful we have grandparents and friends who can enjoy these trips with us when it works out!

  47. Thank you for sharing the magic and spreading the cheer

  48. What a lovely trip – thank you for sharing! I am surprising my husband with a trip to Chicago in mid January. Although we are not going to experience Christmas, or see it with our children, you got me even more excited for a very magical weekend away for two. John Hancock (plus Tilt – Oh God, what have I done?) booked thanks to this post! I can’t wait!

  49. I absolutely love the relationship you have with your dad and his relationship with his grandchildren! This is something I diligently strived for and I believe I almost achieved. I enjoy your dad’s posts when he is in charge of the kids while you are away. I know your life isn’t all rosy but I still love reading your blog and feeling the togetherness of your family!

  50. you have left me weeping with this one.
    chicago is my city. the gold coast is my neighborhood. i don’t live there any more but, man, she’s not a lover you forget!
    i am so glad you’ve confirmed our most recent family idea, which is to do a holiday trip to chicago next year and perhaps for every year after.

  51. Lucy Roach says:

    Completely magical!

  52. I almost peed my pants when you said you would go even if it meant being duct taped naked to the outside of the plane! Your trip looked awesome!

  53. Late to the party! But this post made my heart swell with joy.

    I’ve been on a road trip out west, covering sights like the Grand Canyon and the Rocky Mountains and Las Vegas. I’ve seen three European cities that I miss every single day (especially Amsterdam). I even love traveling an hour north or south in my home state of Indiana.

    But Chicago…
    Chicago has my heart. It’s a home three hours away from home that my fiancé and I visit biannually, now. It’s our dream to make it our actual home in a few years.

    It sucks you in. First visit, you do two or three typical things. Second visit, you do two more. Every visit is different than the last, but the magic is always there.

    “Oh, Chicago knows how small we are,
    How bright she shines in the dark
    Oh, and though I go, she’s in my heart,
    Chicago holds me when I fall apart…”

    – Chicago, by I Fight Dragons

  54. So fun! My aunt took us to Chicago right after Christmas one year so we could go to the American Girl Store. It’s been probably 15 years and I still remember how magical it was.

  55. I loved every bit of this post! What a treat! You must feel so fortunate to be able to take these fun adventures with your kids.

  56. Elizabeth says:

    Just getting caught up on your blog and got butterflies and teered up a little reading this post. You put into words everything I love about Chicago, especially at Christmas time. Ironically I was there the same weekend for a job interview and can’t wait to call this beautiful city home (I’m originally from Memphis, TN and will graduate college in May). Always love hearing someone talk about the butterflies Chicago gives them because I’ve always felt the same way!

  57. Chicago is magical in winter! We were there the weekend before you went and it snowed the prettiest snow. I am from WI so I have seen my fair share of snow but there is something breathtaking about fresh snow in Chicago. We have been there plenty in summer but I think we’ll have to start making yearly trips there in winter as well. I had almost the same list as you but some we didn’t do that will be on the list for next year! By far the kid’s favorite was ice skating in Millennium Park and the hot chocolate!

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