Labor Day is on its way (at last!) and while lots of lucky folk will be taking off for vacations, not all of us are leaving town. For those (like me) who want to make the most of the long weekend at home, its staycation time! And we have all your top Windy City hotels, restaurants and activities to make it count.
You have three nights before that early Monday-work night turn in, so there is plenty of time to hit up some of the comfiest beds, taste the best restaurants and try relaxing or exciting Chicago activities. We have three hotels, one for each night (or one for all three) to make you comfortable and ready for a fun fall ahead.
For a classic Chicago spot, the Renaissance Blackstone Chicago Hotel has been a staple in the city for more than a century. And if gangsters like Al Capone have stayed there, you know it’s a spot worth checking out! The hotel is close to Lake Michigan with most rooms having full lakefront views (amen!), plus you can walk to the Art Institute, Solider Field and more to take in the tourist sites you might have overlooked by being a city resident. Plus, it recently underwent a multi-million dollar renovation so you will leave feeling like a royal.
Then stop at Wise Owl Drinkery & Cookhouse for brunch! This new restaurant has killer cocktails and Gilt City is currently running a promotion where you can purchase a $49 brunch deal for only $29. The unpretentious atmosphere combined with the local “take it easy” Chicago rhythm is perfect for a lingering weekend meal.
If you want a new spot that’s dangerously delicious without any effort on your part, The Virgin Hotel is your place. Not only is it the first hotel in the U.S. to offer in-room, pour-over coffee service, you can also order food straight from your bed with their mobile app. Yes, actual kitchen-to-bed service.
That would be enough to keep me there indefinitely, but if you do want to leave to visit spots like Eataly or The House of Blues, you can order a Tesla house car to take you anywhere within a two-mile radius of the hotel. We also recommend having the car take you to the Civello Salon, one of our Chicago favorites for beautification! Ask for Jen if you want to take your highlights up a notch (she’s a colorist extraordinaire) but the whole team there will give you a pampering you won’t soon forget.
Just make sure you’re back in time for Chicken and Waffles with Sriracha at their late night spot Miss Ricky’s – you’ll fall back into bed in the best kind of food coma.
And then for some real relaxation, there is dana hotel and spa. In addition to the hotel’s amazing spa amenities like the awe-inducing steam room, you can also call in services like Blohaute to be pampered with blowouts and styling right in your hotel room! This new company is an on-demand service that will make your staycation even easier.
Then venture up to their rooftop bar, Vertigo Sky Lounge, to soak up the remainder of the summer.
To keep your body full while your mind is being pampered, there are endless options in the area. As a Chicago foodie myself, the dana is ideally placed for drinks (think Three Dots and a Dash), a classic Windy City steakhouse (hellooooo Sullivan’s) and another group of Gilt City deals at Pinstripes, which has fun and food (best of both worlds)
Here’s to three days of bliss without ever having to get on a plane, train or automobile (unless its an ordered town car)