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