Conquering My First Chicago Winter

The Coldest (Chicago) Winter Ever

The way 2019 started should have been a huge clue on how the rest of the year would turn out.

I experienced my first snow on January 20^th, 2019 in Chicago, Illinois.

I was born in the Bahamas and lived in Miami for most of my life.

For all of those 37 years, I have been deathly afraid of the cold i.e snow.

Though I traveled frequently, I made sure all of my destinations were tropical in nature.

I had no desire to freeze or the worse for me…wear layers.

Love and Basketball (Chicago)

Basketball changed everything!

It all started with Dwyane Wade choosing the 2018-2019 season to retire from the NBA (National Basketball Association).

This wasn’t just a simple announcement of the final day he would play.

My favorite athlete wanted to “go out with a bang”. He named his exit season “One Last Dance” and starred in a tour worthy of any rockstar.

There were special events held in his honor throughout the season. The most memorable is the exchange of jersey “ceremonies” with top players after each game.

As the number one Heat/Wade fan, I wanted in on the festivities.

One Last Dance Tour

I found out there was a freshly painted mural of him in Little Havana.

I already had the latest Wade jersey with accessories and decided to do a photoshoot tribute to the legend.

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It was a lot of fun! My cousins played paparazzi with an i-phone.

If all the attention I received was any indication, I think I put the mural on the map that day.

I met another fan with the same goal in mind.

After the excitement of the shoot wore off, I felt like I needed to do more.

Wade County

I try to plan one away game trip per season. The idea came to travel to see Wade in his final hometown game.

If you follow the NBA, you would know that Miami had adopted Wade as one of our own.

Our city’s unofficial nickname is Wade County.

But he is a Chicago native. That’s how I ended up almost freezing off my extremities.

No Loop Holes

I found a great deal ($59 per night) on the Best Western Grant Park Hotel through Expedia. It was part of the Loop in downtown Chicago and the reviews were decent.

There is a $50 deposit per stay. This is low compared to other hotels.

I used $20 of my Expedia points so I got quite the deal!

I booked about a week in advance. The rate was lower a few months before.

TIP: Price the bundle (air and hotel) packages for an even more affordable price.

The round-trip American Airlines ticket was very reasonable at $131.00.

TIP: Always check AA.com for a basic economy rate. It’s not listed on partner websites and is lower than a regular economy fare. You may board last but it includes a free carry-on.

I realized later that the colder months were Chicago’s low season. So that’s another reason why everything was discounted.

TIP: The Loop has a lot of hostels if that’s your thing.

No Turning Back

I can’t recall the exact moment when I realized what the game’s date meant.

It was being held in January in a northern state known for bitter winters.

This was way out of my Caribbean blood’s league!

The temps would range from the 30’s to single digits.

I have family in New York and I’ve visited countless times. I’ve purposely gone when the weather was favorable!

Be Back in a “Flash” (Wade’s nickname)

Now I had to brace myself and prepare for weather that I was not accustomed to.

I started reading every blog/vlog about Chicago’s winters.

The recurring theme in my research was to avoid traveling at all costs between January and March.

I started getting “cold feet”. The 50 degrees we call “winter” in Miami was the lowest degrees I ever wanted to feel.

Now I was learning about Chicago’s winters being freezing cold because of it’s proximity to Canada. The wind was another staggering factor.

I began to see the trip as a challenge. Looking back, it was no wonder I boldly approached blogging in July of the same year.

What to Wear:

I detest being cold so I wanted to know the best tips and tricks on staying warm.

• The best advice I received from my research was to buy a knee-length puffy coat. It was waterproof with pockets (great for placing your hands for extra warmth). It had a zipper which is another protection from the cold.

I usually shop online. But I needed to make the coat purchase in-store to ensure that I had the right size.

This was all new territory.

Whenever I’ve visited New York, my dad always met me at the airport ladened with coats.

I found this glamourous Jessica Simpson one at Burlington for less than a $100.

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• Layers are important but I ended up overdoing it. I was fine outside but was about to overheat indoors.

My first day as a winter rookie involved taking most of my layers off indoors.

• Most of the advice said to layer with polyester instead of cotton but if you have the right coat, it will give you most of the warmth needed.

One long-sleeved polyester top layer and one layer of tights (cotton) under my sweats/jeans were sufficient.

“You’re Doing It Wrong if you Don’t look like an Eskimo!”

• The detachable fur around my coat’s hood was a blessing against the wind. I made sure to always have a scarf and beanie.

The coldest parts of me are always my fingers.

I bought gloves that should’ve been compatible with my phone’s screen but they weren’t.

I hated having to take them off each time I had to use my phone for a call or pictures.

TIP: I purchased various accessory colors so I could switch up looks daily.

Walmart had great deals on scarves and beanies.

The scarves were under $12 and were very thick and long. I purchased other accessories through Victoria’s Secret Pink.

• My boots were lined and semi-waterproof.

I checked for anti-skid since I didn’t want to be slipping in the snow.

They were on Amazon for $47.00 plus tax and shipping (Woman’s Rylee Fashion Snow Boots). I also purchased thick wool socks and gloves from them.

Lastly, I contacted an old classmate who lived in Chicago to make sure I had everything I needed.

Too Hot

On the day of, I wore a long-sleeved top with a cami underneath and carried my coat. My carry-on was too full for anything else.

Once I arrived at O’Hare International, I donned all of the accessories and an additional top layer.

As I walked through the tunnel leading to the train (and when getting off the plane) it reminded me of walk-in freezers at my past fast-food jobs.

On the train, I took everything off until it was time to exit. I never liked that stuffed look/feel!

Transportation

Airport shuttles are usually my “go to’s” when traveling but the cost was too high from O’Hare to the Loop.

Both Chicago airports have a train connection. Its a more affordable and efficient way of traveling.

I exited the L train near the Chicago theater and Uber’d the rest of the way.

The cold forced me to wait in a nearby hotel’s lobby.

It was such a strange sight to see the fresh piles of snow hugging the sidewalks.

The chill in the air made me excited and fearful! I was afraid if I stayed out too long, I would literally freeze to death.

There is a free trolley service that runs through part of The Loop. I was not about to be outside if I didn’t have to be.

Rideshare

Rideshare was my main mode of transport.

City buses are another option. That would still mean waiting out in the elements.

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This blog documents how I missed my flight for this trip and the basketball game being held the same day. The game was supposed to be the main event!

I was warned that O’Hare had a lot of cancellations in the winter. Adding the airport worker’s strike to the mix, cut my “One Last Dance” tour short.

I was disappointed and wanted to return home. But I persevered.

The fortitude I would need as a blogger was being developed in a greater way.

Where to Eat:

When I searched under “Chicago” in the Essence travel group I’m a part of, YOLK came highly recommended. It was a healthy breakfast/brunch type spot.

There was a location a few steps from the hotel.

I knew to expect a crowd. But I wasn’t about to wait in the long line for my “first taste” of Chicago.

The hotel’s front desk suggested the Eleven City Diner.

It was a Jewish owned establishment that was also busy. They had a bar with minimal wait.

I asked the waiter for a recommendation and it was marvelous.

The selection pictured is Challah (Jewish Bread) French toast covered with strawberries, bananas, and toasted coconut.

A Grain of Salt

Ironically, when I went to YOLK the following morning, I did not like the food!

I ordered the Santa Fe Fritatta. I figured the jalapenos would make up for any lack of flavor.

There was no hint of spice or seasonings. I couldn’t take another bite!

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I let the apologetic waiter know and he tried his best to make it up to me. I went with the fruits and nuts in a pineapple (South Beach) with a muffin

My trip was only a few days so I did not get a chance to try a lot of spots.

I did visit the Navy Pier and they have a few restaurants there.

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There’s a botanical garden, Ferris wheel, and plenty of stores to buy souvenirs.

I ate at Caray’s Tavern and the food was satisfactory!

I searched the Pier’s website ahead of time to familiarize myself with the options available.

A Walk in the Park

The Best Western was conveniently centered across from Grant Park.

I took a walk to take in the beauty of the winter wonderland around me.

This was my first snow after all! Although it was freezing, I couldn’t stay indoors.

Most of the snow had fallen before I arrived but there were light flakes still coming down.

The parts of me that felt the cold was my face and my fingers (whenever they would get exposed). The rest of me was fine.

I wanted to savor every second because soon I would be complaining about Miami’s humidity.

Families were out playing in the snow, a guy walked two dogs and there I was trying to make a video hoping my fingers didn’t fall off.

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Frozen Veggie

My next stop was to Uber to Cloud Gate (“The Bean”) at Millenium Park.

This costly architectural structure was shaped like a bean. It didn’t do anything special!

You couldn’t enter or climb it.

But you can’t come to Chicago without getting a picture around or under it.

It was even more sightly with the snow slowly melting atop it.

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It was a tourist trap and there I was happily snapping away with my fellow travelers.

There was an ice skating rink that took me back to every Christmas movie made in the north.

I was still getting the holiday feels in January. Most of the businesses still had their decorations up.

Let It Snow

I couldn’t leave without touching the snow. It looked just like shaved ice.

The numbness after was worth it.

I’m happy I saw it while it was still white.   

The next day I met my walking tour at Pizano’s Pizza. They are credited with making the first pan pizza.

The tour was booked through Trip Advisor and called Famous Tastes of Chicago Food Tour. It was a 3-hour small group for $63.

I was the first to arrive and waited in the take-out section of the restaurant.

Once everyone showed up, we introduced ourselves and were given a history of pizza and the family. Next, the pie was served fresh out of the oven.

A Taste of Chicago

I expected a firmer consistency and didn’t like the crust. The natural herbs and spices stood out making the rest of the pizza flavorful.

The best part of the tour was the information and junk food (chocolates and popcorn). Goddess the Baker has the best brownie I’ve ever tasted!

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I found out popcorn and brownies originated in the great city of Chicago!

I loved the deep roots found in many Chi-Town restaurants and how they have been passed down from generation to generation.

The black and white photos of previous owners/guests on the wall were an interesting touch. Miami is a newer city and we’re missing that element.

I can’t leave out the Tiffany ceiling at Macy’s. It was gorgeous!

Founding Fathers

Before visiting Chicago, I learned that the founder was a Haitian man by the name of Jean Baptiste Pointe DuSable. (I corrected every person’s English pronunciation of his name in my head!).

He was recently given credit as he was a Black man in those times.  

As a second-generation Haitian, it was very important that I make a visit to his monument.

As we were walking on the tour, our guide passed the area without a word.

I found that strange but I stopped to take a picture.

I wished I didn’t have to rush the moment but I’m grateful nonetheless.

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MLK Day

My visit to Chicago coincided with the Martin Luther King Jr. Holiday and I was able to visit the DuSable Museum.

Once the tour was over, I ride shared over to the south side.

The museum had a full day packed with speeches, dancing, poetry, and dramatization.

It was a family affair and a local radio station was broadcasting live.

The program was such a beautiful and heartwarming tribute to both the pioneer and dreamer.

I felt honored to be a part of the Blackness on display.

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My heart was full.

I had experienced my first snow and felt a deep oneness with my roots.

Satisfy My Soul

A cultural experience surpasses any other while traveling.

I get giddy whenever I can sit at someone’s feet and bask in the knowledge of a people…especially my own.

The artwork and artifacts each tell a story. Beauty and triumph intermingled with hate and violence.

The museum reflected the ever-present contradiction of good and evil. Within its walls, I saw a glimmer of hope and victory!

I conquered my first Chicago winter! It turned out not being as bad as I expected.

My preparation in dressing warmly had a lot to do with it. If you’re considering a trip to The Windy City, follow my tips here and you’ll be fine!

I did not eat a hot dog, visit The Art Institute or attend a Heat/Bulls basketball game.

So a return trip to The Chi is in my future!

If you’ve been, how was your experience?

~Poof…Bee Gone

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