Why Chicago for New Year’s?  I’ve got plenty of reasons.

My first reason would be Heidi.  She desired exploring the bustling streets while soaking up Chi-town’s Holiday vibe.  It also was her birthday this past Sunday, so it was an early Birthday present. 

However, there is a ton of other reasons.  Chicago provides so many different options for eating, from fine dining to the classic staples like hot dogs and pizza.  Not only that,  I wanted to see  Michigan Avenue (known as the Magnificent Mile), view fireworks from Navy Pier and experience the lively downtown atmosphere that lasted till the early morning  hours.

So we were set with dinner reservations, a stop at Navy pier and a room in a classy hotel in Chicago’s Gold Coast neighborhood. 

We arrive in downtown Chicago at about three in the afternoon, our check-in time being now.  The traffic is pretty thick and I’m relying on Heidi, who is referring to her GPS feature on her phone.  I’m stressed a bit and sigh when I finally pull in front of the Thompson Hotel, close to the North end of Michigan Avenue.  The valets take our bags and park our car.  The stress subsides.

A bit of warning if you decide to book a pet friendly hotel and have allergies, ask to be placed on a floor that doesn’t allow pets.  We arrive on the eighth  floor and I feel a weight in my chest, as I smell the distinct scent of wet dog.  Later, I ask if we can move to another floor.  Of course they are booked on New Year’s Eve.  We track down a Walgreen’s and purchase Claritin-it does the trick. 

We change into dress clothes and prepare for our early dinner reservations.  This was my second mistake, although it turns out to be a fortuitous blunder.  I didn’t search for restaurants seriously till Saturday night, December 29th.  Every thing was booked.

My first choice was the signature room on the 95th floor.  It is as it says, a restaurant high atop the John Hancock Center.  However, there were no time slots open.  Which is actually a blessing in disquise, as there is a low lying haze tonight that swallows the tops of skyscrapers from sight. 

There were many restaurants that offered fine dining, finding one with a time slot of around eight was impossible.  Finally I found a place called Steak 48, making reservations for quarter to five.  So, now, we are headed there.

A light rain softly dances against the sidewalks, as we trek through the man made canyon of  towering buildings.  We make the easy hike in only fifteen minutes, but I can’t help feeling the charged ambiance of the city. The trees that line Michigan Avenue are shimmering with lights.  Storefronts of high-end retailers are adorned with classy holiday decor.  Musicians will later play Auld lang syne creating a positive buzz-I can feel the electricity.

We arrive at Steak 48 on time.  After checking our coats and a brief conversation with the hostess, we are immediately seated.  We follow a young woman and climb a staircase, where the lighting is subdued and small candles flicker atop white tablecloths.  The walls are stained wood and boast pictures important to Chicago. 

The service is outstanding.  Genuinely friendly staff members do everything, from tutoring us in vintage wine to taking a picture of us on the patio.  Looking at the menu, I fear asking for the check.  However, it is New Year’s and this is a once in a lifetime endeavor.  So we order a couple glasses of a chardonnay and decide upon fillet mignon’s with Brussels sprouts.

The seared steaks are delicious!  As a matter of fact, so are the brussels sprouts, the wine, heck, even the bread with a buttery glaze is outstanding.  By the way, I have never bit into such a tender cut of beef.

The wait staff checks in on us, but is not overbearing.   Actually, they make us feel comfortable in, what is for me, a very foreign setting.

 Finally, I get the check.  I dropped money for three weeks worth of groceries- a little over $150.  I know, I know, so much for my tagline- Chronicles of affordable sights and travels.  I sigh with the uplifting sense of good food in my belly and a light head from wine -“What the heck, it’s New Year’s Eve.”

Getting around Chicago, as we trek through Millennium Park and find our way to Buddy Guy’s Legends, is easy.  I also feel safe.  Tonight, I stumble upon the occasional homeless person, asking for change.  Yet, not once do I feel threatened in  any sense of the word. 

We head back to the hotel to change into something casual and are off to Navy Pier, a half hour walk from the Hotel.  Navy Pier, to my relief has security tonight.  Every one is patted down before walking into the bustling building of vendors and shops.  Bags are also checked.  Heidi has a purse and I have myself, so we’re separated for an instant.  Given the enormous crowd of a projected 75,000 people, I fear being separated.  However we find each other.

Inside there is a buzz, as frazzled vendors serve a rare volume of patrons this day.  I find a hotdog place and order one.  Then, of course, we step outside.  The pier is packed.  We wait till midnight, taking selfies of us with the city and the enormous Ferris wheel in the background. 

The temps reside in the high thirties and, with proper winter attire, makes for comfortable weather. I hear a faint countdown but can’t make out the words.  Suddenly Fireworks pop, as they appear like luminescent blooms captured by a time-lapse camera.  We share a kiss and enjoy the fifteen minute show. 

As the early morning hours are upon us and the city is alive, our excursion draws to a close.  We walk back to the Gold Coast and find a neighborhood pub that is open till four.  Staying till quarter to three, we finally retire at the hotel, hoping our 2019 is as great as it began.

Safe Travels! 

I am a 44 year old man living in Green Bay, Go Pack!! I love History, give me the origins of almost anything noteworthy and I'm all ears. I also love outdoor activities like hiking, kayaking and camping. However, I don't mind a few days in fresh, bustling cities with interesting historic attractions.

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