Where Do People From Chicago Vacation

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Where Do Chicagoans Flee to When Winter Comes?

So, you wanna know where those hardy Chicagoans escape to when the windchill dips lower than your self-esteem? Well, buckle up, buttercup, because we're about to dive into the great Chicago exodus.

The Great Lake Escape

Let's start with the obvious: the Great Lakes. Now, I know what you’re thinking, “Lakes in winter? You’re crazy!” But hear me out. While swimming might be off the menu, these massive bodies of water offer a unique kind of beauty in winter. Places like Traverse City, Michigan, and Door County, Wisconsin, transform into winter wonderlands. Think cozy cabins, snowshoeing, and hot chocolate by the fireplace. Just don't ask me about the drive up there.

Sun-Seeking Saviors

For those who can't handle a single snowflake, there's always the option of fleeing to sunnier climes. Cancun, Cabo, and Florida are perennial favorites. But if you're looking for something a bit more exotic, consider Costa Rica or the Dominican Republic. Just remember to pack your sunscreen, because going from -20 to 80 degrees in a day can be a shock to the system.

Urban Adventures

Not everyone craves beaches and sunshine. Some Chicagoans prefer to swap one concrete jungle for another. New York City, with its endless energy and cultural offerings, is a popular choice. Or maybe you’re more of a foodie? Then cities like Austin, Texas, or Portland, Oregon, could be your jam. Just beware of the hipster beards and overpriced avocado toast.

The Midwest Alternative

If you're looking for a quieter escape, consider exploring other parts of the Midwest. Places like Branson, Missouri, offer a mix of entertainment and natural beauty. Or, for a truly unique experience, head to the Amish country in Indiana. Just remember, no electronics, and you might want to brush up on your horse-and-buggy etiquette.

How to... Plan Your Chicago Escape

  • How to choose a destination: Consider your budget, desired activities, and tolerance for cold weather.
  • How to book accommodations: Book early, especially during peak travel times.
  • How to pack: Layers, layers, layers! And don't forget your sunscreen (if you're heading south).
  • How to survive the flight back: Bring plenty of snacks and entertainment.
  • How to recover from jet lag: Drink lots of water and try to stick to a regular sleep schedule.
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