The Perfect Surprise Staycation At The Robey Chicago

I’ve always thought about indulging in a staycation somewhere in the city. Usually, it never pans out, getting lost in the comfort of our home and the chaos of our schedules. We always end up questioning ourselves, asking why we would spend so much money when we could just stay at home? We may still go out to dinner and have a few drinks afterwards, but it typically ends with me falling asleep on our couch.

This year for our anniversary, Mark asked me not to make any plans – our ritual in past years has been dinner at a restaurant neither of us had been. However, when I got home from work Sunday afternoon, I was instructed to pack an overnight bag. WTF? He also said that we had to leave soon, so I had to be fast. That’s a tall order for someone like me who packs and unpacks about a hundred times before I leave. I grabbed my Everlane Weekender and excitedly started throwing things in it. Thankfully, in the fury, I remembered such things as my phone charger and toothbrush (most of the time I forget). The best part was that I barely had enough time to pack, let alone try to anticipate where we were going. It was a total surprise. He had planned the perfect staycation.

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I couldn’t believe it. At 5pm we pulled up to The Robey in Wicker Park. I had done a piece on the boutique hotel for the blog previously, and was dying to come back and check out the rooms. Score! Our room was a suite on the top floor – and oh were those views good! The window-lined wall showcased a perfect, sunny skyline. Perfect church steeples dotted the rest of the view which looked south. I swore I could see my childhood home, though Mark firmly said I could not. Regardless, words could not explain my excitement.

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The room, just like the hotel’s common areas, had a unique mid-century modern design to it, and the masculine minimalism made it easy for me to snap magazine worthy photos. The entire wall behind the bed was lined with cloudy, textured glass which housed the long bathroom. Le Labo Santal33 products garnished the bathroom sink and shower, which caused another moment of excitement for me, as this is one of my favorite scents.

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We were very tempted to raid the mini bar as it was stocked with all of our favorite things, mainly St. George Spirits that we fell in love with in San Francisco. We contemplated fixing our own drinks in the room and sitting at the marble table in the corner gazing out over the city, but decided to check out some of the hotel’s other areas.

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We had dinner reservations, another surprise, later that evening, so we headed down to the 2nd floor lounge for a cocktail. It’s a large space with sections of couches and a large table in the center. It’s open all day so you can find people having business meetings, enjoying a coffee, or lounging with a cocktail like us. It would be a perfect place to host a Mad Men-style party with its central bar and low-sitting couches.

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Dinner was at sushi hotspot, Juno, in Lincoln Park. We both had been wanting to dine there for a while, so I was elated when the car pulled up. We tend to go overboard when order, especially sushi. It felt like we had everything on the menu – at least the Nigiri we crushed in about ten minutes. The kitchen sent out some of the best bites of the night, particularly the King and Queen Juno rolls. They were by-far my favorite. We paired sake with dinner, Mark choosing a Daiginjo, and I opted for a Junmai. I wish I had snapped more photos from dinner, but I was in a flurry of excitement, and the food was coming so fast.

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Once dinner was over, we weren’t quite ready to call it a night, so we headed back to Wicker Park for a nightcap. One of our favorite restaurants in the area is Publican Anker, and conveniently, it’s located across the street from The Robey. Our liquor of choice is always Bourbon, so Mark ordered me a Willet 12yr and for himself a 20yr Pappy Van Winkle. Pure Heaven. Seeing as sushi rarely fills either of us up, no matter how tasty or how much we eat, we ordered a few of Publican Anker’s vegetable-driven dishes to snack on with our whiskey. Towards the end, in true fashion, Mark ordered burgers to-go (he’s done this every time we’ve dined here) – it turned out to be perfect, soaking up whatever alcohol was still in my system, and allowing me to have a hang-over-free morning!

In the morning, with no plans for the day, we slept in, heavily. We weren’t on vacation, and didn’t feel the need to explore, so we just enjoyed the long morning. I grabbed us some coffee and bagels from the 2nd floor, and we ate them on the marble table in our room looking out at the city, reminiscing about the night before. We slowly showered and packed. I begged Mark to let me take home the robes, but alas, his logic won out, and we left them behind.

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This little staycation ended up being exactly what we needed. It allowed us to really focus on ourselves and each other. We were able to take our minds off work and household duties like cleaning and paying the bills. We came back refreshed and inspired. I’m already planning our next staycation, and so should you!

Robey Staycation Zara Shoes


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Local Hospitality

I am a hospitality consultant and content creator focused on food, beverage and travel.

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