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.
Can I just say how IMPRESSIVE Chicago’s public transportation system is? I didn’t have to Uber or Lyft not once here! It was a total shock to me coming from NYC (home of the most unreliable transportation system ever) that the trains and buses were not only RELIABLE they were clean & so easily accessible. An example of how easy it is to navigate on the Chicago Transportation System: There’s a train station right INSIDE the airport that takes you directly to the city!
I purchased the 3 Day Unlimited CTA Pass for $20 which got me everywhere I needed to go during my stay. This made budgeting for my trip that much easier, I didn’t have to worry about overspending for transportation!
One thing I was NOT trying to do this weekend is spend an obnoxious amount of money on my hotel accommodations. Especially when I have the intentions of being out and about in the city & not just staying cooped up in my hotel room. So when I found The Found Hotel for under $30 a night I immediately booked!
It’s a bit confusing because it is a hotel but simultaneously a higher end hostel! You are able to book a room that you can share with a roommate with a private bathroom or book a room with your own bed + private bathroom! After my Iceland experience I was open to the shared roommate option, but guess who lucked out with NO roommate during her entire stay, if you guessed me? You’re correct! Just one of the perks of traveling during the low season – so I had the room to myself for three days. WIN!
Chi-Town MUST VISIT Attractions + FOOD:
I came to Chicago with one mission, to take in as much of the city I could and stop at some of the most iconic places in the city! One thing I noticed is that Chicago takes it’s tourism game seriously. They have amazing options for tourists to view the city such as the Go Chicago Card & Chicago City Pass.
These options provide packages that give you access to some of the windy cities most popular attractions! I chose to get a Go Chicago Card and got the three attraction explorer pass! Basically instead of paying full price for each of the places I visited, I got a discounted price + ability to skip the line. I definitely recommend using for those looking to tour the city! Please note you are able to customize and choose different options for Go Chicago Card!
Attractions that I visited while using my Go Chicago Card included:
Of course there are other tourists attractions you can visit for free! Including Millenium Park, Cloud Gate aka The Bean at Millenium Park, the Chicago Riverwalk, Lincoln Park Zoo, Navy Pier (attractions aren’t free though) and more!
Now when it comes to FOOD I gotta admit the Chi-Town has impressed me once again! You can’t hit the town without trying their famous deep dish pizza and I have to admit I never really cared to try it but since in the city I felt like it wouldn’t be right if i didn’t! And man I did not regret it at all. I had deep dish personal pizzas at both Lou Malnati’s & Giordano’s and both were delicious! Do I see myself eating it everyday? Absolutely not BUT if visiting the city it’s definitely a must have.
Some other notable restaurants I visited were: Pink Taco, heads up the service sucks but the amazing grilled fish tacos + sangria make up for it, The Hampton Social (and of course took a pic with their famous “Rose All Day” sign), BeatNik which is COMPLETE instagrammable vibes & Terzo Piano, located inside of the Art Institute of Chicago that will add a major taste of elegance to your trip!
Cold. Frigid cold. If you’re visiting Chicago in the winter time you’ll need to bring all your winter accessories: scarves, gloves, thick socks, ear muffs, ALL of that. I was bundled up a majority of my time here and happy I was as prepared. Preparation is key when it comes to tackling the weather. Wear layers, wear your warmest jacket & you can win the battle against the Chicago winter weather.
Why YOU Should Travel To Chicago:
Whether you travel solo or with others I definitely recommend Chicago as a MUST VISIT city. Filled with tons of culture and fun – you can do it all here. Whether you came to visit art, eat some amazing food, see some amazing views or all if you’re like me – Chicago is the home for it all. Best part is it won’t cost you an arm and a leg – we stan an affordable getaway and the Chi-Town is that.