Snow, Sips, and Sweet Moments: Valentine’s Day in Chicago

Last Valentine’s Day, Devon and I escaped to Chicago for a romantic weekend that was equal parts indulgence, adventure, and quiet connection. We started with dinner at Maple & Ash, our absolute favorite. Walking in, the sleek modern space is warm and inviting, with an energy that feels celebratory without being over the top. Each dish is elevated, think perfectly seared steaks, delicate seafood, and inventive sides that are as beautiful as they are flavorful. The service is impeccable, always knowing just the right moment to pour wine or share a clever tasting note. It’s the kind of place where dinner stretches into an experience rather than just a meal.

The next night, we ventured to Bazar Meats, a steakhouse like no other. From the moment you step in, you know it’s about theater and flavor. The menu is playful yet precise, with meats carved tableside, flavors balanced perfectly with creative sides, and cocktails that make you pause and appreciate the craft. The ambiance was lively, yet intimate enough that we felt tucked away in our own little corner of the world.

Between meals, we treated ourselves to AIRE, my personal favorite spa and bathhouse, for massages that melted away every bit of tension. The setting is transformative, the soothing combination of warm waters, soft lighting, and aromatherapy instantly transports you. We moved from baths to relaxation lounges, feeling the city’s buzz melt away as skilled hands worked magic, reminding us that a weekend like this is about slowing down, reconnecting, and indulging in experiences that rejuvenate body and soul.

Evenings included strolling through fresh snow, laughter, and cocktails at Dearly Beloved, and a show-stopping Justin Timberlake concert that filled the night with energy and music. The combination of intimate moments and big-city excitement created a Valentine’s Day we’ll never forget. From Maple & Ash to AIRE, from snowy sidewalks to stage lights, Chicago gave us the perfect backdrop to celebrate love, life, and just being together.