A Chicago solo trip during the holidays? Yas I made it happen! Chicago has ALWAYS been one of those places I’ve wanted to visit but for some reason never brought myself to go… but when I spotted a major flight deal & the urge to have a quick little getaway, I found myself hopping on a flight to the Chi-Town and it was totally worth it!

I know what you’re thinking, Chicago during the winter? One of the most frigid cities in the US during the cold? 1. Yes, a little crazy but 2. There’s a reason behind the madness! Similar to NYC, Chicago is known for it’s holiday spirit during the holidays and I wanted to witness it in all of it’s glory! Plus if i can trek my way to Iceland solo, three days in the Chi won’t hurt me 🙂 But let’s get into the details of my trip!

Watch My Solo In Chicago Vlog Here:

Booking My Chicago Trip:

Caught this flight deal via one of my favorite airlines: JetBlue – what I personally love about JetBlue is that they are consistently providing affordable flight tickets but still give EXTRAORDINARY customer service. I’ve been flying JetBlue for years and honestly cannot say I’ve ever had one bad experience. I spotted the deal on another favorite traveling tool of mines SuzzTravels which always updates with the latest flight deals. After playing around my flight ended up costing me approximately $128 RT – #winningmuch? And I booked this about 2 weeks ahead of my flight!

I opted for the carry-on option, which JetBlue is one of the few (if not the only) airline that still provides free carry-on. But if you want to check in you can also do that as well with prices starting from $30 for your first bag. From NYC to CHI to flight took a little under two hours.