02/23/2026
Chicago in the winter? Absolutely. ❄️
This past weekend, I enjoyed a fabulous quick getaway to Chicago with family—three adults and two girls (age 12)—and it was the perfect mix of cozy, fun, and memorable.
We stayed at the beautiful Sheraton Grand Chicago Riverwalk from Saturday afternoon through Sunday morning, and it made the ideal home base. The Ogden Suite comfortably fit all five of us, featuring one bedroom, two full bathrooms, a small kitchen, and a spacious living/dining area with a Murphy bed and sleeper sofa. Bonus: our suite overlooked the river—such a special touch.
One of the best parts? The hotel’s location. It’s within walking distance of so many iconic spots, so you can truly enjoy the city without needing a car.
Before check-in, we spent time at the incredible Museum of Science and Industry. One of our favorite exhibits (included with admission!) was the Paul Tazewell Broadway Costume exhibit—so beautifully done and a hit with everyone.
For dinner, we walked just one block to Monarch & Lion for a cozy British-inspired meal. I had a refreshing Pimm’s & Lemonade along with the Truffle Pot Pie—highly recommend!
The girls were thrilled to stop by the Jellycat Store Chicago on Michigan Avenue, while the adults loved visiting the stunning three-story Starbucks Reserve Roastery Chicago along the Magnificent Mile. Even in the cold, the energy of the city was alive—especially with the trees glowing under sparkling lights.
On Sunday morning, we bundled up and walked over to Millennium Park to see Cloud Gate (aka “The Bean”). It was chilly, but the sunshine made it absolutely worth it.
There’s truly no shortage of things to do in Chicago—whether you’re visiting for a quick overnight, a full week, a family getaway, romantic escape, or solo trip.
✨ I’d love to help you plan your perfect Chicago getaway! When would you like to go?
