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 Late Fall Midwestern Getaways

Happy November! I hope All Hallow’s Eve went without any ghoulish surprises this year and was lots of fun. Now that November is here, fall is in its final few weeks. The leaves are falling rapidly, the colors have changed, and the weather has turned much more brisk. It’s delightful! With four weeks left until Thanksgiving and four weeks between T-Day and Christmas, now is the time to plan a last-minute fall getaway. With limited time to spare, a getaway that’s closer to home makes much more sense. For those of you Chicago-based or Midwest-based, I have five late fall getaways to put on your calendar. It’s a great time to travel to any of these locations because the height of tourist season is over. Rates are dropping and crowds are thinning. Take this as an opportunity to explore each of these Midwestern destinations at your own leisure…