This was our fourth annual Christmas in Chicago Weekend, a tradition born from an impromptu decision four years ago when– after too many days of Florida heat and missing all the winter magic of the Christmases I grew up with–I couldn’t take it any longer and made an impulse ticket purchase, hell bent on giving my kids a taste of winter wonderland. I knew exactly where to take them, a city known for its holiday enchantment and one that feels like home, growing up in the Midwest.

For four years, Chicago has delivered.

I can’t quite explain exactly what the magic is.

There’s no guarantee of snow, but that doesn’t matter. There is an electric Christmas spirit that overtakes the city like a storybook spell, evident in window front displays; street performer songs; garland and twinkle lights garnishing the stoops of brownstones, hotels, department stores; pink-cheeked kids bundled up in their finest coats on their way to Christmas teas and Santa lines; crowds sipping spiced wine in outdoor markets; horse-drawn carriage rides; warm glowing scenes behind the frosted windows of coffee shops and Christmas bars while shoppers warm up, catch up, drink up…you can’t help but feel excited when you’re there.

We went straight for Level 10 holiday magic the night we arrived with a ride on the Polar Express. I’ve tried to purchase tickets for this for three years, and finally made it happen. It did not disappoint.

I teared up the second we stepped off the Metra into Union Station and saw all the families in their Christmas pajamas–dads in peppermint stripe flannel, moms in fair isle long johns, babies and toddlers in candy cane sleepers and more Hanna Andersson than I’ve ever laid eyes on in one place. The whole Polar Express production team was so fully and passionately in character, it felt as real as ever. I was as mesmerized as the kids were as we boarded the train, waving to the conductor who welcomed us, overwhelmed by the music and lights and the feeling that we really were on our way to the North Pole.

(Nella plugged her ears in the beginning to get used to all the sounds–ha)

The conductor punches the ticket just like they do in the movie, scattering hole punches all over the kids’ heads. :o)

And the hot chocolate dancers…so enthusiastic!

If you’re in the Chicago area and have ever considered The Polar Express, it’s so worth it (especially for little kids).

One of Lainey’s favorite things about our Chicago trip now is reuniting with her best friend who moved away last year. She was like my fourth kid, and we pick up where we left off every time we see her.

Our most festive outing in Chicago is our Christmas Tea at the Drake Hotel. This isn’t Dash’s jam yet, so he gets go the Chicago Conservancy with my dad while the girls go to tea. Nella was very into her new purse filled with treats for tea. She kept unzipping it and pulling out her Pez dispenser. :o)

Drake Mirror Selfie.

We did not intend to buy an American Girl doll while we were in Chicago, but we had one of those “When in Rome” magic holiday moments in the store, and I know our window for these sorts of things is closing. One call to Vacation Brett, and we had an emphatic YES. She chose Samantha.

…and a memory we’ll never forget was made.

Dash’s companion for the trip was a little smaller–Snowflake, his beloved elf. Santa gave us special permission to touch our elf for this trip which allowed Dash to give Snowflake the Chicago tour of a lifetime. Totally making a book with these.

Snowflake even played Christmas Bingo with us one morning…and won!

More than anything, what we love about Chicago is huddling in at the end of the day–knowing it’s cold outside, but we’re in for the night. We stay at a dear friend’s apartment, and it is set up with so many thoughtful touches from Christmas sheets on every bed to a tiny secret room full of toys. That’s where our most special holiday memories happen every Chicago trip.

My sister and my niece surprised us (I knew she was coming, but no one else did) Friday night at our favorite pizza place and stayed the rest of the weekend in the city.

Per tradition, we went to the top of the city–the observation deck of the Willis Tower–early Saturday morning. We took pictures on the glass floor and put together a puzzle on the floor in the corner because we did it once four years ago, and we’ve done it every year since.

And Christmas in Chicago wouldn’t be the same without a trip to State Street Macy’s with the iconic Christmas window displays (they were so good this year!) and the ornate ceiling and the skinny escalators that lead to never ending levels including Holiday Lane where we always buy the annual Macy’s ornament.

And Garrett Popcorn…(Snowflake chose cheese & caramel mix)

The kids fight over who gets to hold the bag while we walk.

We had a short-lived magic moment–a tiny dusting of snowflakes that lasted all of five minutes but did not go unnoticed by the kids. They screamed and ran outside, attempting to catch a few flakes with their tongues. It was over as quickly as it started, but Lainey tipped her head to make sure I saw the flakes on her hair for proof it really happened.

For the rest of the trip, we explored streets, looked for Christmas trees in windows, rated front stoop decor and stopped for hot chocolate when we needed a break.

I soaked up every sight, every sound, every feeling, grateful for all of it.

Another one in the books.

And now to continue to the magic at home. So much to look forward to this week!

 

A Short List of our Christmas in Chicago Favorites
We don’t do all of these every year, but we try to hit as many as we can while still making room for quiet time together.

Macy’s on State Street – This one we never miss. Iconic Christmas memories

Christkindl Market – It’s PACKED–like keep-your-kids-close-to-you kind of packed, but if you arrive when they open, it’s a little better. Gorgeous handmade gifts, German food, hot Gluehwein.

Top of Willis Tower (or John Hancock Building) – We love the glass floor walk-outs of Willis Tower, but John Hancock Building is a little less crazy and has a little bar and tables where you can sit and sip.

Butch McGuire’s – The most festive Christmas Bar–lights everywhere, trains circling the ceiling, ugly sweaters as far as you can see. Go for lunch for less of a crowd. Otherwise, expect to stand in line outside for a bit.

The Drake Hotel – We go for the official Christmas Tea, but it’s worth visiting just to see the tree and walk around inside. Also festive and fancy: The Peninsula, The Allis.

The Polar Express – Wear your pajamas. Book tickets early.

Chicago Pizza – We could brawl it out over where to go — Gino’s, Giordano’s, etc. But we love Pizano’s for the memories.

Old Water Tower – A damn Christmas dream at night. Dash’s favorite place to hang out because horses and carriage rides.

Garrett Popcorn – Don’t leave Chicago without it.

Millenium Park – Carolers at the Bean, ice skating at McCormick Park

The Churches – Walk in one of the cathedrals during your stay. Make a small donation. Light a candle. Sit in a pew, close your eyes and whisper all your gratefuls. Beautiful, sacred spaces (and this is coming from not-a-church girl!). One year, I want to find a holiday choir concert to attend at night, hopefully with candlelight.

Neighborhood Walks – Find a charming brownstone neighborhood, preferably with a library. Walk the streets with hot cocoa. Heaven, I tell you.

Zoo Lights at Lincoln Park Zoo – Go only if it’s not a bitter cold night (last year, the kids were so cold). If you get a good mild night, it’s incredible. And FREE!

Things we haven’t done but want to some December:
White Christmas sing-a-long movie night at Music Box Theater, Navy Pier Winter Wonderland, Christmas Trees of the World at Museum of Science and Industry

Right in the middle of the witching hour last week, between begging Dash to “Please stop erasing!” while he attempted to finish his homework and scraping burnt potatoes I neglected to turn, the doorbell rang.

“Just a package!” Brett hollered as he opened the door and brought the package inside. “Something from Pinhole.”

Which could only mean one thing. The Annual Family Album had arrived. Screw the potatoes. Forget about the homework. Everything can wait. The family Christmas present we give ourselves every year had arrived–a year’s worth of memories and moments preserved in a book to save forever–and we were pausing everything to enjoy it.

Our annual family albums (we do the 8×8 hardcover albums from Pinhole Press) have become one of the most cherished things in our home, left out on the coffee table for us to look back on our memories all throughout the year–and we do…a lot. The kids pick up those albums and look through them at least once a week; remembering vacations and beach days, birthday parties and quiet weekends; noting people they love; laughing at story recollections triggered by photos.

The thought of creating a family album can be daunting for many though, especially if your photos are all stuck on your phone. If creating an album has been on your bucket list but you don’t know where to begin, here are some album creating tips to help you make it happen in 2020.

Set Manageable SUSTAINABLE Expectations
For me, this is it–the number one commandment for all creative projects, and the sole reason ideas either become  checked off accomplishments or eternally loom in the Creative Purgatory of talked about dreams. If the expectation is too big and elaborate to fit with my current responsibilities, my creative project will likely either never get started or will start with an impressive bang and then fizzle into the graveyard of Fun Ideas I Once Had. When Lainey and Nella were babies, I fell down the rabbit hole of elaborate digital scrapbooking which sucked up what I’m guessing was a good 700 hours of my life–which is why after two years and four albums of novelesque documentation and artistic design, that hobby crashed hard. With three kids, work and our growing list of responsibilities and interests, I know if I am going to keep the tradition of designing and printing family albums of our memories every year, I’m going to need to keep it simple. I don’t add text or stories (would take too long and make me get behind), and I don’t design the pages myself anymore. I drag and drop our photos into Pinhole Press’s album templates (clean, minimal and classic!), and I follow an easy chronological design layout (album starts in January and ends with December). There’s very little thought or decision involved which has allowed me to stay productive and keep up on our albums for three years now.

Gradually Create Your Album Throughout the Year
Most album websites allow you to start creating a project, save it and edit it for as long as you like. I start our album project on the Pinhole Press website in January and drop photos into layouts, adding pages as the year progresses–birthday parties, vacations, everyday loveliness in our home, etc.–and then save it. By the time December rolls around, the album is practically finished. It’s never a big looming project because I complete it little by little throughout the year.

Set Yourself Up for Success with a Photo Organization System
Creating an album is a lot more challenging if you’re trying to choose pictures from a giant mess of random photos. The end of the year is a great time to set up a system for storing photos for 2020. I have folders saved on my computer in chronological order. Within each year photo (2017, 2018, 2019), there are subfolders titled by their dates first (arranged in chronological order) and a descriptions of the photos in that folder such as “Mother’s Day Isle of Capri”, “Key West,” “Lainey’s Birthday,” “Weekend at Home,” etc. If nothing else, create a folder for 2020 and in it, create subfolders for each month. Then, when you pull photos off your camera or phone, you can drag them to where they belong.

Create a Monthly Routine for Transferring your Photos from Phone/Camera to Saved Folders on your Computer
The more your photos build up, the more likely you are to abandon plans for doing something with them. Try and transfer at least your favorite photos you’ve taken once a month into organized folders. If you edit your photos, try and maintain a simple monthly editing process (I do this every week, but that’s because I take a lot of photos). Set a number goal so it doesn’t become too overwhelming such as aiming to edit 15 favorite photos every month. And BACK THEM UP! I back up all my edited photos to Amazon Photo storage.

Set Monthly Goals for Photos You Want to Take
Want to create an album of family photos but haven’t taken enough photos to fill it? Or don’t know what photos to take? It’s easy to have great intentions for photos we want to capture and even easier to forget. I recently went into my photo folder to pull some photos of my kids with Brett’s mom for a gift idea and was appalled that I hardly took any this year. If you struggle to remember to capture photos, set some goals for this year. Join a photo challenge group online for some inspiration or subscribe to one of my favorite photography inspirations magazines, Click. Take a look at the photos you’ve taken this year and make note of who’s not showing up in the photos (Is it you? GET IN THERE, GIRL!). Write a list of photos you want to capture this year or create a fun monthly challenge. For 2020, I’m setting an alarm to go off on my phone on the first of every month with a reminder to capture a candid family selfie with all of us in it so we have a fun progression at the end of the year. Capture photos of your children doing what they love–playing basketball, video games, reading, whatever!–so you can remember who they are outside of posed smiling-at-the-camera shots. Capture what happens in your kitchen, meals at the table, afternoon walks. These are the moments you want to fill your album with.

Work Backwards
Have thousands of photos from the past ten years that you want to put into albums but don’t know where to start? Work backwards. Start with 2019–ten photos from each month, and work them into an album. Then tackle 2018, 2017, working backwards. Or leave everything the way it is, start fresh with a 2020 challenge, move forward and be happy that you at least started somewhere!

Done is Better than Perfect
Don’t stress over having to have the most beautiful photos, or page layouts being cohesive, or whether or not your photos came from a camera or a phone. Just make an album with what you have–photos that you love–because done is better than perfect.

To making more new memories in the new year and capturing the love we want to remember!

We are in an exceptional window with our kids’ interests right now as the span between a 6-year-old and a 7th grader leaves a broad range of gift possibilities. I’m thrilled that remote controlled cars and baby dolls still make Santa’s list and yet also delighted to see Lainey’s wish list take more of a tween turn as she’s drawn to Vans, cheek highlighters and the perfect pair of skinny jeans–things I love too. This gift guide includes some of our most played with toys, new things I know they’ll love today and some timeless gifts that work for any age.

1. Klutz Fashion Look Book – This one’s a fun one for Lainey–lots of fashion inspiration, design prompts and face canvases for makeup. Add a pack of Prismacolor pencils, the BEST art colored pencils.

2. Taco & Tortilla Set
We don’t have a play kitchen anymore, but my kids still love their play food and set up their own little restaurants in Dash’s bedroom. This taco set is adorable and comes with all the fixings for you to customize taco orders.

3. Dinkum Dolls
I wish I would have discovered these dolls sooner–so precious, amazing quality and definitely dolls you’ll save forever. The accessory sets are amazing as well (the outfits!).

4. MagnaTiles
I think I put MagnaTiles on every holiday gift guide because they are the ultimate gift for any age. Kid already has MagnaTiles? More MagnaTiles are good too. The more you have, the bigger you can build your cities and buildings. MagnaTiles are the one toy I’d put in an Airbnb if I owned one and the toy I’ll save forever to pull out for kids who visit. They work for such a broad range of ages of promote creativity and design.

5. Embossing Kit with Heat Tool Bundle
This is a great one for crafty kids. Create your own raised embossed cards with this heat tool, stamp pad and embossing powders. Works with any stamps.

6. OranguTwang
Nella LOVES these kinds of games. This one’s a little bit like Perfection but has a fun twist with the orangutan who hangs from a vine while you add fruit before he “twangs” off the vine.

7. Melissa & Doug Magic Set
A classic little magic set for little budding magicians who think they are the coolest when they make the rabbit disappear into the hat with the magic wand.

8. Stamp Bugs
Another great gift for artsy hearts, this stamp set encourages creativity with a full set of bug “parts” that can be combined to create your own bug design.

9. Karaoke Microphone with Built-in Speaker
This is another gift I add to a lot of my lists because it wins every time. In fact, I should keep 5 of these in my closet for emergency kid gifts. The bluetooth speaker’s built right into the mic, so it’s all you need for karaoke night. Great quality–a much used gift.

10. Hot Wheels Take Apart Custom Car
Dash is all about using tools to put things together and take things apart with no help. He’ll be able to do that with this custom Hot Wheels car.

11. Walkie Talkies
We keep walkie talkies at my dad’s cabin, and my kids think they are the coolest thing in the world. Dash and Nella spend hours walking around, hiding and talking to each other with these things. Plus, they are so great for speech therapy! We noticed Nella working extra hard to clearly articulate in the walkie talkie.

12. PBK Sleeping Bags
I bought these for the kids last Christmas and wasn’t sure if the kids would be thrilled, but they loved them. They love having their own sleeping bags and proudly run to get them whenever we have a movie night. We move our coffee table out of the living room and fill the floor with these.

13. Novagratz Dollhouse
If you want to join me on the dark side in the dollhousing abyss, this is the one that started it all. I love that there are only four rooms and that two of the rooms are significantly spacious–makes decorating a little easier.

14. Polaroid ZIP Printer
I get asked a lot about kid cameras. We have the Fuji Instax camera which is fun for the kids to use and satisfying in the sense that it immediately spits out a photo, but if we are talking photo quality, this little printer is better. It prints phone/iPad photos with the Polaroid app which means you can edit/brighten the photos first on your phone. We love our little printer and take it with us on all our trips. It requires no ink–the chemistry is built right in the photo paper–and every picture prints out on a photo with the option to peel the back off and use as a sticker.