is the founder and owner of Living Colorfully Media, Inc., a boutique social media and marketing firm headquartered in D.C. More recently, she’s also earned the reputation of “D.C.’s Disco Dealer,” since establishing a disco ball business from her apartment during the pandemic. Libby is a midwestern girl, born and raised in Oshkosh, WI (yes, where they make the overalls!), and Chicago holds a special place in her heart.

Known for its rich history, Chicago is a classic American city exuding a distinct vivacity that captures the heart of each visitor. Unlike its New York City rival, you’ll be welcomed to Chicago with open arms, thanks to its midwestern charm and hospitality. And, fun fact: Did you know the world’s first modern skyscraper was constructed here?

As you discover Chicago, you’ll find yourself inspired by its diversity. This city truly has something for everyone. From the Lake Michigan beaches, to the inviting corners of Hyde Park and Andersonville, to the lively neighborhoods of Wrigleyville and River North. The Windy City has a number of personalities, ethnicities, and traditions to enthuse even the most jaded travelers. 

Read on for Libby’s insider tips for your Chicago getaway.

I love the location of this hotel. It’s situated in the heart of the Fulton Market District, which is a trendy and creative neighborhood. The vibe is also so welcoming – mid-centruy design with modern touches. Add on the rooftop pool, Peruvian rooftop restaurant, and happening lobby bar, and The Hoxton is a crowd-pleaser for sure. 

This historic building was converted into a bed and breakfast and it screams hospitality, comfort, and style. If you appreciate a well-designed space that doesn’t overlook the details, this is the hotel for you. 

I have a few can’t-miss restaurants that I frequent on my visits to Chicago. These are all great spots for solo adventures or traveling with others. 

 –  I mean, who doesn’t love a great diner? This Wicker Park restaurant is my go-to breakfast spot. After a night out, order the Back to Life Cocktail which includes shrimp ceviche with crackers (it’s a sworn hangover cure!). There’s more than just breakfast, though. Dove’s serves Tex-Mex diner food at counter seats from the early morning to late at night. And you get to dine to the tunes of  classic Chicago soul and blues. 

 – This restaurant is located inside of a grocery store in Little Village. It’s one of my favorite lunch spots, and I stand behind ordering anything and everything on the menu (I never miss the tacos). Not only is the food great, but the atmosphere makes you truly feel like you’re in Mexico with the fun, colorful decor. 

 – A West Loop staple that offers up a fine dining experience like no other. The atmosphere is super chic without being stuffy. And the team has that notorious Midwestern charm that makes you feel so welcome. Definitely order the chicken liver with grape mostarda!

 – The people-watching at this West Loop cafe is excellent. You can camp out there to work remotely, or just pop in to say hey. I’m not even a coffee-drinker, but the Military Latte is too fun to pass up. It’s espresso, Sawada matcha from Japan, vanilla, milk, and cocoa powder, and it looks like camouflage! Also the donuts are really, really good. 

I’m a sucker for a great vintage shop, and Chicago has so many! Some of my top picks are:

Venture to 

 to get a culture fix. While it might be one of Chicago’s smallest neighborhoods, it’s big on colors, sights, sounds, and flavors!

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