Vacation Glamour

My husband and I both run our own businesses, so finding time to get away is challenging because, not only do we have the many demands of entrepreneurship, but we love to work!

But, with my 8 year old son soon to be on Spring Break, we both agreed that we could afford to take some time off and enjoy a long weekend.  And so, I started looking for a fabulous weekend escape in Chicago… yes, a staycation, although I despise calling it that.

Chicago is filled with fabulous hotels, and when you’re only taking a two day break, why not make it of 5 star caliber?

The Trump Hotel is phenomenal (full disclosure: they’re a PC client). Breathtaking views of the city, stunning service, luxe accommodations and a spa to die for. In fact, you can read the Trump review here.

At Trump, Luxury Goes Big

Peninsula has been a favorite of my husband and me ever since the first time we were able  to afford an overnight stay. The service is just magnificent and when we travel with our boys, they offer amenities for the kids that really make an impact—cookies and milk, a cuddly bear upon arrival and even a tray of movie treats (think popcorn, gummy bears, etc.). My 8 year old is always eagerly awaiting his “VIP” treatment when we check-in at the Peninsula.

Lofty Views -- and service -- at The Pen

Peninsula Spa by ESPA (another PC client) is one of the city’s best and the Friday night chocolate buffet is decadent; thankfully the health club at The Pen is equally impressive.

The fairly new Elysian Hotel on East Walton Street is breathtaking. Rooms are generous, truly living up to the Elysian’s mantra of offering rooms that are more akin to modern residences.  The shopping off Walton Street is some of the best in the city. The last time I stayed at The Elysian I got an amazing rate on the room since I was speaking at a spa convention at the hotel, but I dropped considerably more money down the street at the Tory Burch boutique. And this is another Chicago hotel with a spa that is among the best.

The lobby at The Elysian

Then there’s the James Hotel‘s “luxury liberated” approach. While affordable guest rooms do abound at The James, the high life is found in the 1400 sq. foot penthouse replete with two bedrooms, formal living and dining room, oversized bathroom with his and her sink areas, soaking tub and separate rain shower. I was quoted a rate of $2,500 per night including a personal chauffeur, personal training service, mini-spa services, custom in room dining and a personal concierge.  While that’s a bit out of my budget, I love the concept. After all, shouldn’t luxury be all inclusive?

Luxury Liberated at The James Hotel

And while my search for the ideal “staycation” is taking up more time than I’d anticipated, I’m enjoying the thrill of the hunt. Because when you only have two days to get away, the place you hang your hat for those two days has got to be killer.

What’s the most luxurious “staycation” destination in your city?


Ypu have given me so many ideas for our honeymoon now Thanx a billion!


Would LOVE a staycation at the Trump or Peninsula to try out their phenomenal spas! And I agree, the James is great but that penthouse would be to die for!!


i love "The Pen" too although i stayed there just once. i'm also a fan of the four seasons, it's much cooler than the drake and there are some boutique hotels, like burnham, that are very chic.

Make-Up Your Mind
Make-Up Your Mind

OMG! I feel more relaxed just looking at the pictures! I hope you have a fantastic time!!! Downtown Milwaukee has some beautiful hotels too! The top three are The Pfister, Iron Horse, and Hotel Metro. The Pfister is pure decadence think Gold, rich red and the bar has been voted the best view of the city(which I agree is phenominal) It also is the Home of Janice Salon, which participates in many Pretty City events so for a PC readerlike myself there is always an oppotunity for a discount! (which I agree is phenominal) the Iron Horse, has a fantastic outdoor bar! it's huge with couches and lounging areas, umbrellas, trees.. it's killer. Hotel Metro is a boutique so it's a little smaller, but loaded with charm! it has a shuttle, which is a 1950's English taxi.. So the steering wheel is on the opposite side! It also has a super chic rooftop bar that has a reflection pool and great views of one of the hippest streets in Milwaukee! Thanks for sharing these beautiful places! definitely gives me somethign to aspire to!