As the twins approached their 9th birthday, they asked to have a trip instead of a party. Well, that’s my idea of a good good time, so of course it was a resounding YES! They didn’t have any particular destination in mind, but I did limit them to domestic destinations only. Their birthday is only a week before Christmas, so this would have to be a weekend getaway.
I set them up on the computer and went to skyscanner. I told them to search their dates within the US, and they could choose from the top two most affordable locations. The choices were Chicago and Washington DC. After some back and forth, they finally settled on Chi-town. I was stoked. I love DC, it’s actually my favorite part of the country, but I also wanted an opportunity to experience winter time Chi, too! And, they’ve been to DC a ton of times.
Some people thought we were crazy for going to Chicago in the winter, but I’m not afraid to live on the wild side, lol.
Chicago, the vibrant city known for its stunning architecture, rich culture, and mouthwatering food, offers a perfect destination for a memorable mommy-daughter birthday trip. While winter may bring chilly temperatures, it also brings a unique charm to the Windy City. Come along as I lay out our three day itinerary filled with exploration and celebration, iconic landmarks, delicious dining experiences, and fun-filled activities.
But first, Where To Stay In Chicago
We decided to stay at the Fairmont – Millennium Park in the heart of downtown Chicago. It’s the perfect stay anytime, but especially in the winter months. During that time, the hotel transforms the entire lobby into a warm and welcoming lodge with fun filled events, tableside smores, hand crafted signature drinks, and a specialty menu. Make sure to make reservations for the smores experience weeks in advance of your stay. TIP: If you book through Amex Fine Hotels and Resorts, you’ll get an automatic room upgrade and $100 credit for meals and services on site.
Okay, let’s jump right into the itinerary. Be warned, when we travel, we like to experience as much of a city as we can, so this itinerary is jam packed, but still with plenty of room to experience the unexpected. If you want to get the best bang for your buck while visiting the Chicago, check out a GoCity Pass…you’ll save big on the City’s major attractions.
Day 1
- Embracing Winter Wonder at Millennium Park Start your trip by immersing yourselves in the snowy landscape of Millennium Park. Take a leisurely walk through the park, admiring the glistening snowflakes as you make your way to the famous Cloud Gate sculpture, affectionately known as “The Bean.” Strike a pose and capture some magical mother-daughter moments against the backdrop of this reflective masterpiece. While you’re in the park, definitely check out ice skating if that’s your thing.
- Next, head over to the John Hancock Building and experience the awe-inspiring 360 Chicago Sky Deck. Ascend to the 94th floor for breathtaking panoramic views of the city and its winter splendor. If you’re feeling adventurous, try the exhilarating TILT, a thrilling tilt experience that offers a unique perspective from a tilted glass enclosure. It was super cool and definitely worth the add-on. I’ll be honest, though, the weather was a bit foggy, so our view to the bottom wasn’t as great as it is in the spring and summer months. Still, it was fun and the girls loved feeling like they were tilting over the building.
- Afterward, warm up with a delightful lunch at Russian Tea Time. I’ve wanted to take the girls to a tea time for quite a while, and what better time than their birthday. The tea service was delicious, complete with both savory and sweet treats. The tea was also yummy. I recommend getting the Queen’s tea service and share it with your group. It provides the greatest array of offerings. If you’re not into tea time, have no worries, this charming restaurant offers an array of authentic Russian dishes, hearty soups, and delicious tea blends. Indulge in their signature Beef Stroganoff or the delectable Chicken Kiev…we had both along with our tea time (we were hungry, lol) and everything was delicious.
- In the evening, embrace the winter festivities at Jack Frost Winterfest. This was such a fun event. Beware, this experience is completely outdoors, so dress appropriately and have a winter wonderland blast! There are so many activities to enjoy including, Ice Skating, Snow Tubing, Winter Bumper Cars, Holiday Photo Ops, Full Bars and more! And don’t even get me started on all the instagram-able photo opps; around every corner, you’ll be stopping to get another picture! Be sure to get your tickets in advance because all activities are first come/first serve. Extra Tip: for the grown-ups in your party…get the spiked hot chocolate and thank me later!
- End your day with a mouthwatering dinner at Piquod’s. What’s a Chicago visit without a deep dish experience. During my research, Piquod’s came up over and over as the best in the city, so we had to check it out. It was….an experience. I’ll just say that. Deep dish isn’t my favorite, but it was worth a try and the girls loved it, and that’s what mattered on this trip anyway. .
Day 2
- Get up bright and early and head over to Hyde Park where you can start your with a delicious down home breakfast at Valois. This legendary diner offers an extensive menu with mouthwatering options. Cool, fun fact: This is President Obama’s fave breakfast spot in the city. That definitely sold it for us. I was also pleasantly surprised at the prices as well. You’ll leave full and your wallet will won’t be crying.
- After breakfast, head to the Museum of Science and Industry, a fascinating destination that combines education and entertainment. There are so many cool and interactive exhibits. The girls especially loved the exploring the U-505 Submarine and doing a simulated submarine drive. My favorite part was walking through all of the amazing Christmas trees from around the world. It was quite a site to see and experience.
- Next, you have to take a shopping break along the Magnificent Mile, Chicago’s premier shopping district. After all, if you’re going during the winter season this is your opportunity to grab all those last minute gifts for the family and friends.
- As the day comes to an end, indulge in a fabulous birthday dinner at Sugar Factory. This trendy restaurant offers a whimsical dining experience with over-the-top milkshakes, colorful cocktails, and a menu filled with decadent desserts. The girls selected this restaurant on their own. In all of their Chicago research, this was one of the places they were not willing to compromise on…they had to experience the extravagance in person. It’s the perfect location for a birthday celebration for the kids and young at heart.
Day 3
- We started our final day with a visit to the iconic Navy Pier, a Chicago landmark that offers a multitude of entertainment options. We decided to ride the Centennial Wheel, a giant Ferris wheel that provides stunning views of Lake Michigan and the city skyline. Don’t worry about the weather, luckily the pods are enclosed and warm during the winter months. A Ferris wheel is always a family favorite for us, but these views were seriously spectacular!
- While you’re at the pier, walk into the Navy Pier Shops so you don’t miss the chance to try Garrett’s Popcorn, a beloved Chicago treat. Their signature blend of sweet and savory popcorn is a must-have snack while exploring Navy Pier. Choose from classic flavors like CaramelCrisp and CheeseCorn or try their seasonal variations for a delightful surprise. Can you say hot coco flavor?? Yes, it was yummy!
- Finally, we had a few hours before having to get to the airport, so we wrapped up our trip with a friendly competition at 10pin, an upscale bowling lounge. Enjoy a few rounds of bowling, complete with cozy seating areas, delicious food (the pizza is a perfect pairing for a competitive game between mom and daughters), and refreshing beverages. It was fun and lowkey way to end a jam packed and fun-filled weekend.
All in all, a winter trip to Chicago provides a magical backdrop for a mommy-daughter birthday adventure. From exploring iconic landmarks like Millennium Park and Navy Pier to indulging in delectable dining experiences at Russian Tea Time, Piquod’s, and Sugar Factory, there’s something for everyone in the Windy City. Don’t be afraid of Chicago’s winter weather. There is still so much fun to be had!
Let us know if you try out our itinerary in the comments, and don’t forget to mention your favorite part.
Happy Travels!
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