The holiday season has a way of bringing out the best in us. For Aaliyah, it's not just about the lights, music, or festive activities. Instead, it's about connection. Growing up in Chicago, IL., she's learned that the most meaningful moments happen when she's surrounded by family, reflecting on her roots, and celebrating the strength and love that make her who she is. 

Walking the same path as her mom, dad, aunts, and uncles who have all shared their unique perspective of nostalgic Christmas experience makes her feel like she’s carrying the torch. From the spectacle of the 100-foot Christmas tree at the former Marshall Fields, now Macy's to shopping sprees at the illustrious Magnificent Mile, each year presents another opportunity to bask in traditions while creating her own.

If you're looking for a holiday schedule jam-packed with fun-filled adventures, keep reading to learn more about Aaliyah's top Chi-town picks, which are a must-see. 

1) Harpo Studios

Every holiday, Aaliyah feels excited when she drives past the old Harpo Studios on West 12th Street, where Oprah Winfrey built her incredible journey. This place is like a shining beacon for Aaliyah and all Black families, reminding them that anything is possible. Even though the studio is gone, Aaliyah can still feel Oprah's magic close by at the 'Until We Meet Again’ mural on 845 W Madison St. In that mural, a massive picture of Winfrey, surrounded by beautiful art and culture, shows everyone the power of being yourself. 

One of Aaliyah's favorite moments is when her mom shares stories about Oprah's hard work and the lives she changed. To Aaliyah and other young Black girls, Winfrey's journey proves that dreams can come true. Each time Aaliyah takes a photo in front of the mural, she feels proud and inspired. It reminds her how important it is to see people who look like her doing amazing things, working hard, and helping others. Every visit fills her with hope, knowing she's part of a loving community that lifts each other up.

2) Laughter and Play at Maggie Daley Park

What's the holiday without visiting the Maggie Daley Park Play Garden? Whether she’s sliding down the giant slides or climbing walls with her little cousins, it’s a place where laughter comes easy. 

For Aaliyah, sitting on a park bench with her mom, listening to stories about her childhood adventures are the best. Her mom always ends their special talks letting her know that she is creative and can be anything she works hard for. 

3) Honoring Heritage at the DuSable Museum

Holidays that remind you of your heritage and roots? Count Aaliyah in! And thanks to places like the DuSable Museum, you're always reminded of your culture. She loves to explore the museum with her dad, learning about the inspiring stories of trailblazers who paved the way for future children like her. This visit leaves Aaliyah feeling proud and motivated. 

4) Light-Filled Magic at the Chicago Botanic Garden

Something about the Lightscape at the Chicago Botanic Garden feels almost magical. Aaliyah loves skipping through the glowing tunnels, fully immersed in art in motion with illuminating lights playfully accented by festive music. From start to finish, it’s the ultimate holiday dream experience.

5) Shedd Aquarium

The Shedd Aquarium has always been about more than marine life; it’s about family time. From holding her mom’s hand as they watch the jellyfish to laughing with her friends as they try to mimic the movements of the Beluga Whales. Even more fascinating about Shedd Aquarium is how each animal seems to greet her uniquely, making her feel like she’s gained a new friend with every trip. She wildly laughs as she wanders through the exhibits, led by her curiosity, sparking questions about Sea Otters, penguins, and turtles while Mom and Dad try to keep pace.

6) Sharing Stories Over Hot Dogs at Al’s Beef

What’s a day out in Chicago without food? For Aaliyah and her family, no holiday outing is complete without a stop at Al’s Beef for a classic Chicago-style hot dog. It’s the ultimate comfort food. If you’ve never had a Chicago hot dog, picture this -  a Viennab beef hot dog nestled in a steamed sesame seed bun, topped with yellow mustard, sweet pickle relish, chopped white onions, fresh tomato slices, two slices of pickled sport peppers, a dill pickle spear and a sprinkle of celery salt. For Aaliyah, there’s something special about sitting around a table with her family, unwrapping that perfect hot dog, and sharing stories from the day. It’s more than just a meal; it’s a reminder of what makes Chicago special - a city with rich traditions, deep roots, and a flavour that’s impossible to forget.

Being a native of the windy city means living in a place that oozes big-city vibes, buzzing with energy but wrapped in warmth and intimacy. But, beyond the holiday events and decorations, creating memories with her loved ones and connecting with her community means the most. 

What are your favorite places to visit in your city? Share it in the comments below.