Top Reasons to Leave Chicago for the Winter and Travel

Are you like us and love to call Chicago home but at the same time have doubted your decision to move here during a brutal winter day? If yes, continue reading the top reasons you need to get out of Chicago and do more traveling in the winter.

1. It's always summer somewhere

An iced over lake Michigan is awesome to see once or twice but then it’s just plain cold! With cold so biting it chills you to the bone why not take a month to work remote in the sun filled Caribbean. A little extra sunshine might be just what the doctor ordered!



Frozen over Chicago river during a cold Chicago winter
Frozen over Chicago river during a cold winter


2. Lack of access to nature

If you enjoy the kayaking, hiking, swimming or really any activity in the great outdoors you’re out of luck in Chicago winters. Chicago can be so cold there are almost no outdoor activities 6-8 months of the year. One solution is to spend a couple weeks warming up on the sun-soaked Caribbean islands like Las Islas Del Rosario or exploring the Sierra Nevada de Santa Marta mountains.


Canoeing in perfect weather after escaping Chicago winter
Canoeing in perfect weather


3. Nowhere to take a weekend trip to

Have you been to St. Louis, Detroit, or Gary, Indiana?


4. The wind-chill!

With temperatures that have neared -35 degrees Fahrenheit, the winter wind-chill is enough to send shivers down your back. Have you ever worn two shirts, two sweaters, a jacket, gloves, scarf, hat and still been cold? If not, then you are in for an unpleasant surprise!


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5. Traffic, traffic, traffic

Chicago is regularly ranked as one of the worst cities for traffic. So why not replace your morning commute with a cup of delicious coffee and friendly conversation with your new co-traveling, co-workers?


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6. The darkness

Chicago winters are brutal but walking home from work in the darkness and then waking up and its still dark can be lugubrious. Our body’s need sunlight. Without sunlight our creativity and productivity can be drained. Why go through this when you can work from a sun-soaked Caribbean Island like Playa Blanca.


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