The Drew’s on the Move

What started as a quick trip to Chicago for a wedding somehow turned into a perfectly paced couples’ escape—equal parts iconic sights, indulgent meals, and moments that made the city feel intimate instead of overwhelming—even with the temperature working against us.

Chicago greeted us with –6 degrees that weekend, the kind of cold that makes your eyelashes freeze and turns every walk into a commitment. Somehow, it only added to the experience. Ducking into warm restaurants, lingering a little longer over meals, and holding hands just to stay warm made the city feel even more cozy and memorable.

We stayed at the JW Marriott, which quickly became our warm, luxurious retreat from the brutal cold. Coming back to the hotel after each outing—layers piled on, cheeks still frozen—felt like a small reward in itself and set the tone for the weekend.

We kicked things off the most Chicago way possible: a bundled-up walk to Cloud Gate. No matter how many times you’ve seen The Bean in photos, it still stops you in your tracks. Watching the skyline bend and stretch in its reflection—while questioning our life choices in that cold—felt like our official “we’re here” moment.

From there, we headed straight to Cindy’s Rooftop, where the views of Millennium Park and Lake Michigan did not disappoint. The contrast of icy streets outside and the warmth inside made it the perfect place to thaw out—great food, great atmosphere, and the city spread out beneath you.

Lunch brought us to Au Cheval, where we did it right: one double burger, one single burger, shared between us—plus the fries and the hash browns, because skipping either felt like a mistake. Simple, rich, and absolutely worth the hype. We lingered longer than planned, soaking in the laid-back energy and sampling a few local beers before braving the cold again.

Dinner that night was Maple & Ash, which felt like a full experience rather than just a meal. Dim lighting, bold flavors, and that unmistakable celebratory vibe—it was the perfect escape from the freezing temperatures and a night that blurred the line between wedding weekend and date night.

Before the wedding, we met up for brunch at Trivoli Tavern, a cozy, classic spot that felt tailor-made for a slow, indulgent start to the day. It was the perfect way to fuel up, warm up, and ease into what would be a full day of celebration.

Later, the day leaned a little lighter with oysters at Bellevue—fresh, bright, and elegant, and a welcome contrast that reminded us Chicago does refinement just as well as indulgence.

Before the wedding welcome party, we squeezed in one more memorable dinner at Adalina Prime. Polished, warm, and quietly luxurious, it was the ideal lead-in to the weekend’s festivities and a final reward for enduring the cold.

After dinner, we headed to Moneygun, where expertly crafted cocktails and a low-lit, speakeasy-style vibe made the freezing night outside feel worlds away. It was the perfect place to linger, sip something strong, and officially shift from “wedding weekend” to “couples getaway.”

The wedding itself took place at Salvage One, a venue that felt quintessentially Chicago—industrial, eclectic, and full of character. Surrounded by vintage finds and warm lighting, it was the perfect backdrop for a celebration that felt both stylish and deeply personal.

By the time the wedding events wrapped up, it already felt like we’d had our own little escape. Even at –6 degrees, Chicago delivered—big city energy, cozy corners, and memories that felt distinctly ours.

Sometimes the best getaways are the ones you didn’t plan.