5 Winter Travel Tips: Don’t Let the Cold Stop You From Traveling AND Enjoying It

As a girl who was born and raised in Florida, the shock of true winter in some of our duty stations has been breathtaking (literally). But I refuse to allow the cold to prevent me from new adventures and exploring with my family. And you shouldn’t either.

Winter travel obviously requires a bit more planning and definitely layers, (so many layers) but it can still be an incredible and fulfilling experience for you and your family. It can also be extremely budget friendly, too. 

Did you know Radisson Blu Aqua Hotel, Chicago has a Military 1st Program? This is valid across the board –– even with their affiliate hotels like Country Inn and Suites or Park Plaza and Park Inn. This means steep discounts and free room upgrades, all part of their commitment to serving those who serve in partnership with the USO.

With this in mind, I made it my mission to utilize their hotels for my winter travel. Our first stop was surprising my children with a three day trip to Chicago for Christmas. After registering for their rewards program, I booked our stay with Radisson Blu Chicago. It was so easy and we were told we had the ability to cancel 24 hours before our stay. 

It’s like they knew Murphy stalks us. I was grateful!

Upon arrival (with our two children and two dogs in tow), my husband was greeted with a sincere thank you for his service. We were upgraded to a suite to more comfortably fit our family and fur babies, at no extra cost. When we entered, notes of appreciation and treats for the family were waiting. 

Honestly, I felt like Kevin in the second Home Alone movie. The space was unbelievable and the view was just spectacular! 

While everything was toasty and magical inside, it was a balmy 22 -freezing-degrees outside. Despite the frigid temperatures, we made it our mission to explore Chicago and enjoy the holiday “must sees” in the city. We wisely brought the stroller for our 4-year-old daughter and plenty of layers to minimize the complaints of our never-like-to-be-cold 10-year-old son. 

And those mask-up rules didn’t bother anyone. Heck, the kids even wore them outside to avoid having their faces get cold. It was a solid win in the age of COVID-19 ruining everything with its rules and restrictions. 

The key to making the “travel during winter” work with minimal whining was lots of inexpensive breaks from the cold. Confession time y’all. I am obsessed with coffee and finding unique coffee shops wherever we go. You know what else they have? Cookies, which happen to be a favorite of my kiddos (and most youth of the world, I would hazard a guess). Spending an hour inside of a coffee shop was fun for adults and children alike. Success!

This meant we got to go enjoy the gorgeously decorated and absolutely huge Christmas tree outside in the cold with the surrounding skating rink after that, without a peep of complaint. We followed that with exploring Macy’s and Santa’s Wonderland, which was all inside. 

By the time we headed back to our Radisson, five hours had passed without any tantrums and everyone was riding the high of the Christmas spirit (plus caffeine and sugar, of course). 

Our stay for the rest of the days was absolutely fantastic! When I asked my son what his favorite part of the trip was (I absolutely assumed it was going to involve the cookies) he said walking around exploring. This from the kid who abhors being cold? A huge win! 

My tips and tricks for winter traveling and exploring are pretty simple and straightforward. 

  1. Look for budget friendly options and discounts (like Radisson’s Military 1st Program).
  2. Bring all of the layers and then bring extra. The first thing my daughter lost in Chicago was her hat but luckily I brought extra.
  3. Mix up being outside with breaks inside to avoid meltdowns.
  4. Locations with a cold winter get pretty creative with options for events or things to see. Do some research on winter activities for the place you are traveling to and make it a daily affair determining all the things you’ll do. Ownership and excitement can build, leaving complaints on the cold behind (hopefully).
  5. Attitude is everything. If all you focus on is how gray or cold it is, you’ll miss out on the magic around you.
Jessica Manfre, LMSW: Jessica Manfre is an author and freelance writer for multiple publications. She is a licensed social worker, earning her Master of Social Work degree from the University of Central Florida in 2020. She also holds a Bachelor of Science in Psychology from Northwestern State University. Jessica is the co-founder and CFO of Inspire Up, a 501c3 nonprofit promoting global generosity and kindness through education, empowerment, and community building. She is the spouse of an active duty Coast Guardsman and mother of two. When she isn’t working, you can find her reading a good book and drinking too much coffee.
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