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Visiting Chicago in Winter

Chicago in the winter? Yes, it’s cold, it’s snowy, it’s icy and the wind cuts through your clothes like a knife. But it’s also amazing if you take the time to bundle up and enjoy the sights despite the cold.

I have been to Chicago in all seasons and all types of weather. I love them all. Winter is no exception. Each season brings its own memories and adventures.

Ice on the stair rails

Amazing Views

We were finally able to get to the Light Festival last year. And I am so glad we did. It was a great adventure for us. My children and grandchildren were with us. We had adjoining rooms in the The Royal Sonesta Riverfront with the most amazing view of Chicago I have seen yet.

View of the Chicago River from Royal Sonesta
Night view of Chicago River

Even my adult children were loving the views!

My kids viewing Chicago from above

The Parade

After a day of roaming Michigan Avenue and shopping, we bundled up as warm as possible and headed out to the Magnificent Mile for their Light Festival. I must admit that because of the excitement and the crowds, we didn’t even notice the cold. We were living in the moment.

The city lit up with festive lights and the streets were filled with the aroma of Garrett Popcorn , wonderful restaurants and street vendors.

My Grandson watching the parade
My Granddaughter watching the parade

Walking through my favorite city with my favorite people was one of the best memories I could have created. The sights, the smells, and sounds around me, and the looks in my grandchildren’s eyes will live on in my heart forever.

Always Something To Do

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Winter in Chicago is just a little bit different than strolling down the streets or along the lake on a warm day. We find that we are discovering new things to do. After walking for awhile, we pop into shops that we wouldn’t normally see.

We duck into a warm tavern or coffee shop to thaw our fingers and toes. Some of the taverns and restaurants have large stone fireplaces luring us in for a bite to eat or a sip of bourbon to warm us from the inside out.

Chicago on New Year’s Eve

One New Years Eve we were pleasantly surprised when we came across The Elephant and Castle. We warmed up with a glass of wine and bite to eat in front of the cozy stone fireplace as we watched the snow falling outside and people walking past on their way to who knows where! I love to people watch in Chicago.

Elephant & Castle Restaurant, New Years Eve

After our wonderful dinner near the fire, we ventured back out into the snow, not knowing where the city would lure us next. We found ourselves on the 95th floor of the Hancock Building in the Signature Room Lounge having a drink and enjoying the amazing view.

Fireworks From the Hancock

Little did we know, there would be fireworks at midnight on Navy Pier. So we purchased another drink and they let us stay in our seat near the window to wait for midnight to arrive. It was one of the best times I have ever had while ringing in the new year!

One thing I MUST point out (it’s my best kept Chicago secret!), if you want the BEST view of this amazing city, you have to visit the ladies restroom on the 95th floor of the Hancock Building. I came across this one night while having a drink in the lounge. The second I walked into the restroom, it took my breath away. I could hear other women talking about how they come here and make a fast trip to this room just for the view. Too bad men aren’t allowed!

The entire wall in front of the stalls is glass! There are times I can see the city for miles and miles and there are other times I just watch the tops of the clouds roll past. It never ceases to amaze me… and I always make sure to duck in this space even for just a few minutes!

Don’t Stay Away

So my advice to my readers is please don’t stay away from Chicago because of the cold. There are so many wonderful experiences waiting for you! Great views and amazing shopping or Pub visits, Ice skating on Michigan Avenue!

Take a chance. You won’t regret it! But bundle up!

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