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…

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Last Minute Valentine's Day Gift Guide

Valentine’s Day is a few days away and I know there are a few slackers out there. Whether you need ideas for Valentine’s gifting or you want to give your partner a few hints to make sure they’re on the right track, today is your lucky day. We’ve got a last-minute guide for all the procrastinators out there, especially anyone who is within driving distance of the Chicago metro area. All I know is that if I were to be on the receiving end of these gifts, I’d be forever grateful. This is definitely a gift guide for those who prefer experiences over things so if you’re looking for a few diamonds, keep scrolling…

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5 Fireplaces to Warm Up in Chicago

If you haven’t heard, Chicago is currently surviving another polar vortex. Temperatures dropped to a record-breaking number yesterday causing businesses to shut down and people to embrace the art of hibernation. Those of us who have the ability to hole up in our homes all day without having to leave for even a second don’t mind this one bit. However, anyone who has to brave the cold probably wishes they relocated anywhere else at this point. Regardless, if there’s one thing Chicago knows how to do, it’s survive winter. So whether you love it, hate it, or care less either way, the city has your back. One of the ways we survive the cold temps in Chicago is through fire...literally. Many restaurants, bars, and hotels have fireplaces to cozy up…

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5 Things to Do in Chicago This Holiday Season

It’s the most wonderful time to visit Chicago. Christmas in the city is nothing short of spectacular. The streets are lined with lit trees, decorations are everywhere, and there’s an undeniable spark in the air that you don’t get any other time of year. With so many things to do, I’ve put together five things not to miss this holiday season. I started this round up last year and it felt right to do it once again. With Christmas on the brain, why not?! Next week, I have two Christmas dinners with friends, one at the Walnut Room (pictures for sure coming) and one at Eataly because no one knows how to celebrate Christmas like the Italians...

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6 Cozy Spots Around Chicago

Colder weather calls for cozy get togethers. If there’s one thing Chicago knows how to do well (other than take advantage of summer), it’s survive winter and the colder months. We’re a social city! We like going out for brunch and meeting friends for a cocktail after work. Five months of bitter cold won’t keep us hibernating...well, not the entire time at least. We can appreciate a good occasional hibernation. For those colder months when the tips of your fingers start to turn blue and your nose goes numb, the cozier spot to meet up, the better. Cozy, by definition, means “enjoying or affording warmth and ease.” In my words, that translates to a fireplace, casual and/or comfortable seating arrangements like couches or comfy chairs, and a warm drink with alcohol optional…

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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…

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The 2018 Fall Guide to Chicago

Fall in Chicago is a special time of year. The amount of time we have beautiful, brisk weather perfect for wearing cozy, chunky sweaters is limited as winter and summer fight over the milder season. The trees turn colors and the streets line with leaves of yellow, orange, red and brown. It feels magical and surreal at times that a city could be so gorgeous. If you’re visiting from out of town, hopefully you get to experience one of the more brisk days (like today). Experience what it's like to bundle up while roaming the streets of the Windy City. Whether you’re looking for a comforting bite to eat, need to warm up, or ideas for things to do...we’ve got the ultimate list for fall…

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The Lady Boss' Guide to Chicago

Chicago is one of the best cities for self-employed individuals and entrepreneurs. Going off on my own almost four years ago now, I’ve had the chance to get to know the city in a different way. It became my office playground like many other people who are in similar career paths and work environments. I’ve explored different neighborhoods and found a few favorite spots to return to and a few spots that are better for casual coffees with friends. For a productive day “out of the office,” I learned quick that cafes and coffee shops with a strong internet connection are vital. It’s also a perk if they offer real food and not just snacks or pastries as well as plenty of outlets. To meet with colleagues or clients, it’s important to find spots with a lower noise level or at least moderate so you can have a conversation without screaming. Some of the best spots are tucked away in the neighborhoods of Chicago and others are right in the heart of downtown. All it takes is a little exploration to find the right ones!

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