What’s to Love about Chicago?

The best city in the midwest for discovering more of what you love 


Getting Settled: Lodging and Transportation

For the many times that I have been to the Windy City, I can always say that I’ve had a memorable and unique experience every time. As a kid we used to take family trips during the summer and stay with extended family. Unless you book thru AirBnB or have a hotel discount, lodging in this city can get quite expensive. So bumming a bed or couch with a friend or relative is the best bargain. I’ve been able to stay in a few suburbs while having to drive or take the train into the city limits. I’d prefer the train due to my lack of desire to drive their crazy highways. If you must drive to Chi-town, be sure to plan out your time so that you can park somewhere and walk around the downtown area. There really is no point in driving around downtown because you’ll either get stuck in traffic for 20 minutes just to go five blocks or have to pay for parking guaranteed. The best option is to take the train/fly into the city, book a room thru AirBnB and catch an Uber/Lyft to where ever you want to go.

How to Meet Folks:

Connecting with strangers who reside in Chicago is always fun as the locals are sure to give you the best reviews of places to eat, drink and be merry! It’s always smart to have a function to attend here so that you can network with people of similar interests. I recently visited for an entrepreneurial conference called Think.Start.Do. in the Wicker Park neighborhood and talked to a few cool business owners about what motivates them to stay in this city. The common response was that Chicago is a vibrant city busy enough to keep you interested and competitive enough to keep your hustle game strong. I talked to cultural producers, self-employed artists, Uber drivers, and other entrepreneurial types. I gotta tell ya that this was one of the most motivating trips I’ve had here and I’ve been here over a dozen times. I came to the conference with 3 other ambitious women and we learned so much over the 2-day conference and had plenty of fun too. Another cool way to meet people who are interesting is to sign up for a seat with Creative Mornings, a breakfast networking lecture series for the creatively inclined. If you are too late to get your ticket for the next session, the next best option is to sign up for nearby events on Meetup.com or TicketLeap.com. Always a great way to meet new people!



Hit the Streets: Eateries and Experiences

Whenever you visit Chicago, or any city for that matter, always make time to visit a residential neighborhood with local mom-and-pop businesses to support. I’ve always loved to support small business when I travel because they are the souls that make a city worth living in. They add to the culture of a place much better than those brick and mortar developments. So when I get good recommendations from local residents, I make an effort to stop by for a visit. Below is a short-list of those places I’ve visited, those hard-to-pass-by spots or referrals from a friend:

Hopefully this post inspired you to take an adventure to the Windy City. I’m never disappointed from visiting here! If you do swing by any of these hoods, let me know if you enjoyed it. Take a photo and tag me on social media by adding @LeFloreCreative.

Discover More. Travel More. Live More.

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