Chicago Winter Wonderland - 1 Day Itinerary: Ice Skating, Holidays, Afternoon Tea, Sip 'N Skate

Sip N Skate in Chicago: 1 Day Adventure from Detroit!
Join us as we embark on a whirlwind 1-day trip to Chicago, where we "sip and skate" our way through the Windy City's best wintertime spots! With just over 8 hours to explore, we made the most of every moment. Here's how our incredible day unfolded:
🛫 Starting Point: We flew out of Detroit in the early morning, landing in Chicago ready for adventure.
☕ Stop 1: Willis Tower & Skydeck
We kicked off the day with coffee and breakfast in the Willis Tower lobby before heading up to the Skydeck for breathtaking views of the city skyline. Perfect way to start the day!
🍹 Stop 2: Cindy’s Rooftop
A short walk led us to Cindy’s Rooftop, where we soaked in panoramic views and enjoyed a refreshing cocktail to toast the day ahead.
⛸️ Stop 3: Millennium Park Ice Skating
Next up, a quick walk brought us to Millennium Park, where we laced up our skates and glided on the seasonal ice rink. The iconic Chicago backdrop made this experience magical.
🫖 Stop 4: London House Afternoon Tea
To warm up, we walked over to London House for a cozy holiday tea service. The festive atmosphere and delicious treats were the perfect midday pick-me-up.
❄️ Stop 5: Jack Frost Pop-Up at Fulton Market
A taxi whisked us to the Jack Frost Pop-Up, where we sipped on festive cocktails and hit the ice again for more skating fun. This spot is full of holiday vibes!
⛸️ Stop 6: Maggie Daley Park Skating Ribbon
Another short taxi ride took us to the Skating Ribbon at Maggie Daley Park. This unique ice-skating trail winds through the park and offers a one-of-a-kind experience you won’t want to miss.
🎄 Stop 7: Christkindlmarket & Macy’s Window Displays
We strolled past the downtown Christkindlmarket, soaking in the holiday magic, and admired the festive Macy’s Window Displays-a Chicago holiday tradition.
🍽️ Final Stop: The Allis at Soho House
Our last stop was dinner at The Allis inside Soho House, where we enjoyed a delicious meal and one final sip to cap off our incredible day.
💡 Tips for Your Sip N Skate Adventure:
Bring your own skates if you have them-most rinks allow it!
If you have more time, consider visiting a museum, going shopping, or exploring Chicago’s incredible speakeasies and restaurants.
The holidays make this trip extra special, but it's a great itinerary any time of year.
📍 Why You Should Do This 1-Day Trip:
Chicago’s holiday magic, vibrant food and drink scene, and iconic skating spots make this the perfect day-long adventure. Whether you’re a local or flying in for the day like us, this itinerary packs a lot of fun into just a few hours.
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