When I was a child, we had occasional girls' outings where my mom, sister, sisters-in-law and I would spend a day shopping and as adults we’ve done a couple sisters overnights. It’s been quite a few years since we did something like this. My mom has been gone two years now. The siblings have all moved far apart. Those traditions are something I loved.
Since I am a mom of five boys, doing a girls' day was something that had disappeared. I didn't have daughters to repeat the ritual with. However, last Christmas season, I was able to recreate those girls' trips that I loved with my two teenage nieces. Since they live in Central Illinois, they haven’t seen much of Chicago. So last year, I invited them to come up and do an overnight in the city with me in December. I've always loved being in the city around Christmas and was excited to share that experience with them and show them some of my favorite things and places.
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We stayed at The Drake, which is a perfect spot to make as your home base for a couple of days of shopping and eating along and around the Magnificent Mile. The weather was about as expected for winter in Chicago and we bundled up and walked from place to place. We arrived in the morning and after we checked our bags, we snapped pics in the hotel’s lobby, which has a beautiful tree. Then we headed out down Michigan Avenue to do some shopping and marvel at all the lights and decorations.
We did a little shopping at the 900 North Michigan Shops and stopped at the Fourth Presbyterian Church. We weren’t able to go inside, but walked through the courtyard and took some pictures of this gorgeous Gothic Revival church built in 1914. Then it was on to the Water Tower Place for some more shopping and lunch in the food court as well as a taste of some Chicago classics - Garrett’s Popcorn and Do-Rite Doughnuts.
We went back to our room to warm up a little bit before dinner. I was fortunate to have won a one-night stay in an Instagram contest and we spent the night in the Princess Diana Suite - a six room, 1,500-square foot suite overlooking Lake Michigan, Lake Shore Drive and the Gold Coast. Princess Diana had stayed in the suite for three nights in 1996 while in Chicago for a fundraiser for cancer research at Northwestern Hospital. I definitely felt like a princess lounging in the large bedroom and soaking in the tub and having snacks in the large dining room.
We were undecided on what to do for dinner, but with us visiting on a Monday night we were lucky to be able to get a reservation at one of my favorite Chicago dining destinations, the Signature Room. Located on the 96th floor of 875 N. Michigan (formerly the John Hancock Building), the sunset views are stunning, but we were there a little later in the evening after it was dark. We were, however, able to take in the breathtaking view of the city all lit up. It's amazing.
I had hoped to enjoy afternoon tea at the hotel with the girls, but it’s definitely something you have to plan ahead for and make reservations well in advance. Since it was full, we set off for more shopping. We hit Water Tower Place (again), the Shops at North Bridge, Block 37 and some of the other shops along the way. My niece wanted to go ice skating so we headed over to Millennium Park. Unfortunately it was all sold out. That is one lesson I learned on this trip is it’s hard to wing and if there’s something you really want to do, check into making reservations or pre-ordering tickets. There were still some limitations and COVID precautions that might have made it more difficult than usual, but definitely plan ahead.
It was nice watching the skaters at Millennium Park as well as seeing the tree and getting that mandatory selfie in front of The Bean. Another thing they really enjoyed was stopping off in front of the Wrigley Building to watch some street musicians play. We lingered for a while and they made requests.
We also made our way over to the Christkindl Market at Daley Plaza, another of my favorite parts about the holiday season in Chicago. We wandered around among the booths, had hot cocoa and I finally got to try out the raclette that has always tempted me in photographs. It’s quite a show just watching it made - a warm wheel of cheese that is skimmed off onto a lovely loaf of baguette.
One tradition that I always loved about being in the city in December was checking out the window displays at Marshall Fields (and later Macy's) and going inside to shop. It was also time for dinner so we thought we would check out the food court, which happened to be closed when we arrived. The Walnut Room was bustling and I’d never eaten there during the holiday season, but always wanted to. As luck would have it, they were starting to shut down, but I figured it couldn’t hurt to ask if we could get a table. They were able to squeeze us in and we enjoyed dinner beside the big tree. There was also a princess making her way to tables to sing and grant wishes. It was a lovely time. We also took time to gaze up and take pictures of the Tiffany Dome the world’s largest unbroken Tiffany mosaic - with 16 million pieces covering 6,000 square feet. If you’ve never stopped in to see it, be sure to do so.
We only spent a total of about 30 hours in the city, but we packed a lot in. It was so fun spending time with my nieces, getting to relive the tradition of the girls’ shopping trip with another generation and seeing the city I love so much at the most wonderful time of the year. I definitely recommend making it a tradition!