My Christmas Weekend in Chicago with Zoe

Last weekend officially launched the holiday season for me when I took my granddaughter Zoe for a Christmas weekend in Chicago. We stayed in a one-bedroom apartment I found on Airbnb and spent most of our time shopping while taking in a few sights.

One Bedroom Apartment in Chicago, Illinois


Our girls weekend was something I’d been promising her for a while and I thought November would be the perfect time to go when decorations are up but before the sidewalks get crazy with holiday shoppers.

Since I wanted Zoe to experience what it’s really like to live in the city, I chose a one bedroom apartment to rent in a prime location – just a few blocks to the Michigan Avenue Magnificent Mile but also within walking distance of the iconic Macy’s store on State Street.

One Bedroom Apartment in River North Chicago


I’m kicking myself now for not getting night shots inside the apartment so you can see how pretty the nighttime view of Chicago is. The daytime view is pretty spectacular, too.

Shabby Chic Style Flat in Chicago


The city apartment has a kitchen but we didn’t use it. We ate all our meals out. Just beyond the kitchen is a balcony where you can get an even better view of Chicago streets. We could see the Hard Rock Cafe’s famous guitar sign from the apartment.

Apartment Kitchen in the Heart of Chicago


The bedroom is super cute but I wasn’t used to the city sounds. I swear a siren could be heard every hour through the night. Plus the first night there were political protesters a few blocks away chanting for about an hour.

Shabby Chic Bedroom in the City of Chicago


Kitty corner from our apartment building is the Holy Name Cathedral. I love all the architecture I saw during our Christmas weekend in Chicago. I’ve seen a lot of it on previous trips – I need to go back just to take more photos of everything.

Holy Cross Cathedral in Chicago


I told Zoe’s mother to pack comfortable shoes because I planned to walk everywhere during our Christmas weekend in the big city. Like I said, I wanted her to see what it was like to actually live there. We crossed the famous Chicago river while making our trek to Macy’s store on State Street. The river is dyed green for St. Patrick’s Day. Zoe says she’d like to see that.

Chicago River and Skyscrapers


One of the big four skyscrapers surrounding the Michigan bridge crossing the river is the LondonHouse Hotel. It was sporting a big festive wreath for Christmas.

Christmas Wreath at LondonHouse Chicago


About a mile later we made it to Macy’s (formerly Marshall Fields) on State Street. If you’re going to spend a Christmas weekend in Chicago, Macy’s is a must see with their holiday windows and decorations!

Macy's Christmas Decorations in Chicago


Macy's Christmas Decorations in Chicago


Christmas Window at Macy's in Chicago


I promised Zoe a few new clothes so we stopped in the girls’ department before making our way to my favorite place in the store – the Walnut Room with its incredible Christmas tree! You can dine in the Walnut Room by the tree. We were going to have lunch here but Zoe begged for Subway’s instead. I gave in since this weekend was more about her than it was about me.

Christmas Tree in Macy's Walnut Room - Chicago on State


Note how the roof and room changes color.

Christmas Tree in Macy's Walnut Room - Chicago on State


The theme of Macy’s Christmas decorations this year is “Believe.”

Christmas Tree in Macy's Walnut Room - Chicago on State


After leaving Macy’s we visited a new-to-me store that I absolutely loved. It’s called P.O.S.H. and had the most wonderful assortment of Christmas decor and vintage finds.

Christmas Weekend - Posh in Chicago


This is my new favorite store in the city. Zoe wanted a book about manners that she found here – which totally took me by surprise but I did get it for her. I should ask her if she’s learned anything yet!

Christmas Weekend - Posh in Chicago


Saturday night we visited the Disney store where she picked up Pua from Moana. From there we went to dinner at Harry Caray’s restaurant in Water Tower Place. Of course, once she had Pua, she had to take him everywhere.

Dining with Pua from Moana at Harry Caray's in Chicago Water Tower Place


We took the train to and from the city for our Christmas weekend. Except for the Uber ride to and from the train station, we walked everywhere.

Pua the Pig from Moana


Next weekend hubby and I are headed to the Chicago Botanic Garden for their holiday lights tour. We’re staying at another Airbnb place just down the street from the famed house in the Home Alone movie. I’ll be sure to get more pictures!


See More Points of Interest:

Christmas in Galena, Illinois

Scenes from Door County, Wisconsin

Fall on the Farm in Southwest Michigan

My Trip to Cozumel Mexico


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  1. What a treat…for Zoe and for all of us who see the beautiful pics!! Thank you for sharing! I need to do something special like that for my 2 young granddaughters, you’ve given me some great ideas. Happy Thanksgiving and Merry Christmas to you and your family.

  2. What a wonderful holiday trip for you and Zoe. Thanks for sharing! I can tell Pua enjoyed it, too! Your pictures brought a smile to my face. 😊. Happy Thanksgiving & Merry Christmas!

  3. Looks like so much fun, Jennifer! I’ve never been in Chicago other than the airport and a hotel nearby. Hmm, this is making me think I need to visit around the holidays!

    1. Hi Tamara! It’s a great place to visit any time of year – except maybe January through March because the weather is wacky. The streets are clean and most of the shopping areas are beautified with landscaping and flowers. Everyone is really friendly too, which is a little surprising for a big city. You’d love it!

  4. Jennifer,
    P.O.S.H. is one of my favorites in Chicago. Sign up for their emails. Things change there all the time. So glad you found it. Loved reading about your girls’ weekend. It is hard to tell who had more fun! I never thought about an Air BnB when we stay in the city…it’s always a hotel. Thanks for sharing your memorable weekend.

    1. Hi Donna! We walked past P.O.S.H on our way back from dinner the first night at Weber Grill. After seeing the store windows I made note to return the next day. I’ll definitely sign up for their emails. Thanks for letting me know about that. Such a neat store!

  5. What a wonderful trip for the two of you. Memories made !!!!
    Any chance you would share exactly where you stayed it looked lovely.
    I always find looking for a suitable lodging thru AirBNB like looking for a needle in a haystack. Recommendations are sooo much better.
    Thank you

  6. Awesome trip! What wonderful bonding memories you are making. You are a sweet, generous and smart Grandmommy. The apartment looked amazing and it sounds like you picked the perfect places to visit. Soooo fun! Can’t wait for the pictures from your and hubby’s trip!

  7. What an enjoyable post! Of course, I always enjoy your posts. 😊 It brings back memories of the many visits we made to Chicago when my hubby was a school board member. Their annual convention was the weekend before Thanksgiving. We had such fun in the city, which was surprising for this country girl. I loved shopping while hubby was in his meetings. The big Disney parade, kicking off the Christmas season, was on that weekend too. We usually watched from our hotel window. What fun memories. Thanks! I bet you and your granddaughter made lots of great memories too.

    1. Hi Kathi! I’m so glad you got to experience Chicago during the holiday season. There’s a magic about the city at Christmas time. Watching the parade from the hotel window was probably a smart choice since the streets can get crowded. I’m more of a country girl too but I always enjoy Chicago.

  8. Your granddaughter is so cute and i think looks a lot like her grandmother. Know you had a good time and made wonderful memories , Submarines, isn’t that just like a kid! Lots of magic around the holidays in the big cities. Thanks for sharing this warm experience with your granddaughter.

  9. I am so glad you and Zoe had such a lovely time. The pictures were beautiful. These kinds of memories are the best !!

  10. I’m sure Zoe loved her trip! I can’t wait to take my granddaughter to theWalnut Room, it’s such a magical time. Of course if she prefers Subway, so be it. I’ve heard of Posh, but haven’t been. Sounds lovely. Do they still have the huge tree in the middle of the Store? Macy’s that is.

  11. Lived in downtown Chicago and Near North for a decade, moving there right out of university. This brought back some fond memories, especially the photos of Marshall Field’s (now Macy’s). It’s a wonderful city and I still miss it. Thanks for sharing.

  12. What a special weekend for the two of you! We’re headed to Chicago on January 2 and my fingers are crossed the holiday decor might still be up! xo

  13. Subway over the Walnut room? Zoe! Lol!!! Jennifer you have to be the best grandmother on the planet. What a wonderful trip for you and Zoe. That AirBnB was perfect. I agree with another poster that it’s hard to find a good place to stay just looking online. I put a fan noise app on my p[hone so that when we travel it muffles out the noises..especially on a cruise if your in a busy walkway with young teens up all night.

    1. Hi Lori! I agree with you about choosing Subway over the Walnut Room. I was disappointed we didn’t get to eat there but – the weekend was about her so I caved. Ha!

  14. Just loved the reprise of your visit to downtown Chicago. I lived there and shopped what was then Marshall Fields for many years and still miss it. For the first months I lived in Chicago I stayed at the YWCA on Oak that was subsequently converted into a podiatry clinic, not far from the cathedral and steps away from Oak Street Beach. So nostalgic.