Chicago – Day 1 of 2: theWit, ROOF on theWit and BOKA

Chicago is truly one of America’s great cities and other than a brief visit to what I now know as The Loop for an afternoon during a layover fifteen years ago, I never really had a chance to experience it. All that changed this weekend as Hilton invited me to “Be A Weekender” and experience the best Chicago has to offer.

theWit Hotel Chicago

Hilton’s Be A Weekender campaign, and the website, offer complete weekend getaway planning. It’s a great idea and when you consider there are only 52 weekends a year, it’s good to have a one-stop-shop for weekend fun. The well-designed and content-rich website, with access to the huge range of great Hilton brands, offers tips, deals, destination suggestions and more.

After arriving in the city I caught a cab to theWit Hotel, a stylish and luxurious DoubleTree by Hilton property right in the center of the city’s downtown Loop. The hotel is beautiful, with a very hip lobby and great first impression. After a quick check-in I made my way up to my accommodations for the weekend, the hotel’s fabulous Paramount Spa Suite, which is fully LuxuryFred-approved (video suite tour HERE).

View of Chicago

This is a huge, 815 square foot residence in the sky, surrounded by floor-to-ceiling windows, which look out onto the amazing Chicago skyline. I walked in at dusk and the lights of the buildings were beautiful with the buildings themselves still visible in the fading light, like a movie set. The suite was truly baller-status with a large living room with a 42″ HDTV and a sofa bed for unexpected guests. There was a dining table and chairs, again very stylish and then a large kitchen. It was a great open floor plan and I was willing to move in and live there, if they would let me.

The kitchen led into the entry hall, which then led to the first bathroom. This was a full one, with bathtub and a window looking out over the city. The hall continued to the baller master bathroom. This had a huge spa tub with a large window, offering what may be one of the best bathtub views in the world. There was a large glass-walled shower and both sinks were very cool, modern and flat.

theWit bathtub
Best bathtub view in Chicago

After the master bathroom the hall led into the large bedroom with king bed. This too had the walls of windows with incredible views of the city skyline, Lake Michigan, Millenium Park and the Chicago River. There were two closets, a large desk and work area and another big HDTV. There was a also a sitting area by the window, with incredible views up Lake Street and even a slice of the Chicago River by the Trump.

The Wit
My bedroom

After a far-too brief rest in the suite, I headed upstairs to ROOF on theWit, the hotel’s ultra-cool bar, lounge and nightspot. On Friday and Saturday night (and Sunday afternoons) the 7,000 foot space becomes the city’s hottest club with world-class DJs and an incredible live performance (dancers and acrobats, etc.) and light show to rival the big Vegas clubs.

BOKA Chicago

After drinks, we hopped in a cab and headed to BOKA, one of the city’s best (and most popular) dining spots. As a first-timer to Chicago, it was cool to see the famed Steppenwolf Theatre Company across the street. The spot, now helmed by chef Lee Wolen, has earned a Michelin star for the past four years and the honor is well-deserved. They serve what’s known as contemporary American cuisine with an empasis on fresh, local ingredients. The food is excellent and the atmosphere warm and friendly.

COrn soup
Corn soup with peekytoe crab

Our wine was a lovely Sauvignon Blanc from New Zealand. A single-vineyard selection from 2013 that was light, crisp and perfect for the wide range of dishes we all ordered. I’m always one to try the most unique thing I see on a menu so I went with the roasted venison loin. The fact that it was paired with grilled sausage made the choice that much easier. It was juicy and tender, joined perfectly with huckleberries, turnip and kale. To start I had the corn soup, delicious, with peekytoe crab, pickled blueberries and tarragon. Just a wonderful blend of flavors.

Roasted venison loin

Full, smiling from the wine and happy, we returned to theWit where I was greeted by the night view of the city, equally wonderful yet different than the dusk view I was greeted with earlier.

State STreet
State Street and the lights of Chicago

Read about Day 2 in Chicago HERE
Read about Day 3 in Chicago HERE

My Chicago “Be A Weekender” adventure was sponsored by Hilton. Check out to plan your own adventure.