There’s something decadent about running away… without actually going anywhere. No flights, no packing tetris, no frantic last-minute search for your passport. Just you, a hotel key, and a city you think you know, until you slow down long enough to see it differently.
If you’ve ever wondered how to plan a staycation, this is my favorite answer: treat your own city like a destination. A staycation in Chicago is less about staying put and more about slipping into a romanticized, luxe version of your everyday life. The version where time feels stretchy, food tastes better, and your only job is to notice how good it feels to be taken care of.
Sounds nice, right?
The Upscale Check-In
If a staycation has one rule, it’s this: pick a hotel that feels like a treat, not a compromise. For this staycation, that meant The Peninsula Chicago.
Everything about it whispers you don’t usually stay somewhere like this: polished marble, a spa with a near-mythic reputation, and guests casually sporting Cartier bracelets. Meanwhile, I walked in with a hair tie around my wrist and a very specific craving for room-service fries.
The moment the elevator doors closed, I felt my shoulders drop. The room was spacious and serene, the kind of space that quiets you without asking. Crisp sheets, a bathroom you briefly consider moving into, and a view that made Chicago feel like a city I was meeting for the very first time.
There’s a particular thrill in checking into a hotel fifteen minutes from your apartment. It’s indulgent in the best way — a tiny rebellion against routine, wrapped in marble and room-service menus.
Where I stayed: The Peninsula Chicago
Eat Like You’re Traveling
When I’m away, food shapes the day, so on a staycation, I follow the same instinct. For dinner, we finally went to Mako, the omakase reservation that’s had a firm spot on my list for two years — mainly because no occasion ever felt “nice enough.” Turns out, this was exactly the occasion.
Each bite was better than the last, made even sweeter by the gift card a friend gave us to soften the sticker shock.
Mornings look different, too. Instead of oatmeal at home, I wandered out for a flaky croissant the size of my hand and an extra-strong latte; proof that staycation coffee hits different when you’re not rushing anywhere. Or, you can order pancakes to your room and pretend you’re the type of person who lives like this all the time. Can’t go wrong either way.
Where I ate: Mako
Drinks, Always
One of my favorite staycation ideas is to map out a mini bar-crawl of sorts. Start at a tried-and-true classic, wander to a new cocktail spot that’s been sitting on your list, and end the night at the hotel bar (always the right call). Here’s how ours played out:
Maple & Ash for the upscale, unique cocktail
Hugo’s for that perfectly old-school energy
Z Bar for a skyline nightcap inside the Peninsula
There’s a special kind of fun in being a local with tourist energy — the freedom to both explore and rediscover.
Where I drank: Maple & Ash · Hugo’s · Z Bar
Be a Tourist in Your Own City
A staycation in Chicago is the perfect excuse to finally do the things you recommend to visitors but never make time for yourself. For me, that meant a couples massage at the Peninsula (truly one of the best massages I’ve ever had) and wandering the Gold Coast side streets with no agenda except “let’s see what we find.”
No purchases were made — unless you count the three items currently sitting in various online carts, taunting me.
The beauty isn’t in the activity. It’s in moving through your own city with curiosity instead of efficiency.
What I did: Spa at the Peninsula · Window shopping downtown · Long river strolls
Slow Down, Stay In
This might be my favorite part of any staycation: the permission to do absolutely nothing. Sleep until your body decides it’s done. Read a book in bed. Take a long shower with no timer running in your mind. Order dessert simply because the room service menu suggested it.
This is the part people forget when they ask how to plan a staycation: the goal isn’t to fill the time. It’s to soften it.
The Joy of Staying Local
By the time I checked out, I felt lighter. More rested. More in love with a city I already live in. That’s the beauty of a staycation: all the joy of escape, none of the exhaustion.
You walk back into daily life with fresh eyes, reminded that adventure doesn’t always require distance, sometimes it just requires slowing down.
Until next time, Chicago.