I finally made it to Chicago!

I want to start by letting you know how badly I want to visit Chicago again. What a charming city Chi-Town is. I left with a handful of friends and a whole mess of memories to look back to for when I’m ready to book my next trip. This was one of the best solo-trips I’ve ever taken on my own.

Chicago is the ideal city to visit if you want to travel on your own and as you continue reading, you’ll completely understand why. First of all, I had zero to no knowledge about it. I didn’t know what to do, where to eat, WHERE TO GRAB A CUP OF JO! I practically was a NEWBIE to the city, but as you know me by now, I travel like a local, so I decided I wanted to play the city by ear and ask anyone that I would come across what they recommended I do…

Are you ready?

There was only one hotel(hostel) I knew I wanted to stay in Chicago and that was The Freehand (which, I’ve recommend in Miami/LA before). I knew what to expect: A cozy ambiance, bohemian vibes, chicness, mostly centrally-located, a great scene, and a lot of solo-travelers like myself getting to know each other in a very cool Broken Shaker Bar just downstairs in the lobby.

How I was going to manage to stay there affordability?

Last minute trips are always the hardest. Hotels are either fully booked or the prices have ranked up to double in just a few days. So I sticked to what I knew best – HOTEL TONIGHT. The app that’s proven to me time and time again that it’s never too late to book a room for somebody traveling with a low-budget (specially for my solo-travelers out there!). I was able to book my hotel room instantly at the lowest rate possible a few days before departing to Chicago. I felt so lucky.

Arriving to Chicago, I was a little bummed due to the weather. It was FREEEZING and gloomy; two things that shouldn’t mix together when one is traveling alone, right?

So of course, I wanted to check-in early and lay low in hopes that the sky would clear up a little. I was delighted to find out through HOTEL TONIGHT that I was eligible for early check-in without having to contact the hotel. Which is why I love using this app for last minute vacations. I was able to communicate with HT Pros (a chat room inside HT App dedicated to helping customers with any questions). What really took me by surprise was the communication. I was super hungry(hmm, more like hangry!) and didn’t exactly know where to grab brekkie. So I asked the HT Pros if they could recommend anything for me and I got closed to ten places with detailed information about them!

I was so surprised!

I’ve never experienced that in any other app. I was so thankful, because even though I didn’t know much about the city, I was able to get my hands on some local favorites to dine-in!

After check-in and laying low, I was able to finally checkout the famous bean! I was so stoked to see it at large. I walked right across from it and made my way to the rooftop of the Athletic Hotel called Cindy’s. The view was so so beautiful. I made my way to the bar and made conversation with everyone. When I first started traveling alone I was so scared to talk to strangers, but once I became comfortable it became easy to read people and allow myself to exchange a few sentences. It takes a few trips and a little bit of confidence to do this, but I know you got this if you wish to put yourself to the test!

Chicago was pretty much like this for the entire weekend I explored it. I took plenty of Ubers and made conversations with the drivers, I walked around the city on my own and sometimes with the friends I made, and took photos of everything I could. Some of my favorite moments were sharing a cup coffee with strangers at the Soho House or having a girl’s brunch with a friend of a friend at Rose All Day.

I cannot wait to roam around the city of Chicago in a warmer summer day! Because I don’t think I can visit when it’s cold again!


Book your stay with Hotel Tonight & stay at The Freehand*




This blog post is sponsored by Hotel Tonight, but all opinions, photos, stories are my own. the integrity of this blog and you matter to me.

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