Checking In: An Iconic Hotel by StayPineapple

Being a local to Chicago makes me one of the luckiest people when it comes to a staycation. Instead of airfare, I pay a round-trip price of $16 to get to and from the city and can plan a trip around hotel prices. Plus, the location can’t be beat. Even New Yorkers get out of their city when they take a staycation. I mean, that’s why the Hamptons exist, right? When I’m desperate to get away but don’t have the time or bandwidth to plan an actual trip, I’ll open Hotel Tonight or check a few of my favorite hotels in the city to see where I can find the best price…

5 Places For a Quick Fall Getaway

Before diving head first into the holiday season, plan a quick getaway to relax and enjoy the final weeks of the season. It seems that most of the US had a somewhat late summer this year which means the fall leaves are appearing and sticking around later than usual. Thanksgiving is a month away and it starts the insanity that is the holiday season, but not if you start preparing now! In the meantime, give yourself a break by taking a quick trip away from everyday life. These five destinations have a mix of warmer and colder fall weather but each is a strong contender in its own right. From New England to California, whether you have a regular weekend or a long weekend, these are worth a fall getaway…