6 of the 7 Continents For The Budget Traveler: New Year's In Chicago

New Year's eve or day is by far my favorite holiday. I think maybe this is because for a long stretch between being a bartender and a cop I wasn't allowed to have the holiday off. But now for the last 11 or so years I have spent New Year's in a different city or country every year. Australia is the only continent I have not spent New Year's on and that is soon to change ;)

Anyway, I decided to ring 2018 in by going to Chicago. I had done a big NYE the prior year in Egypt and wanted to do one small/domestic. Like many of my trips I was told by some friends and of course tripadvisor trolls DON'T GO TO CHICAGO FOR NEW YEAR'S IT'S TOO COLD!!! Well, one, I love to go places in off peak season to see the real city vs the tourist city, two, it's a lot cheaper this way, and three, I don't decide what day New Year's can fall on.

Now going in I had a tough guy attitude about the cold, I mean, I grew up in New York City, I've been to Moscow and St. Petersburg in the winter time. Iceland, the Swiss alps, Alaska etc... how cold can it be? I will say here for the record, to this stay standing at 44 countries and thousands of cities, Chicago New Years was by far the coldest place I had ever experienced. I could not walk a few streets without having to walk into a store and pretend to be interested in buying something just to warm up! But that aside, I can also 100 percent say to this day, Chicago was by far my best domestic New Year's ever.

Here's my points on what made it awesome for me, where I saved a ton of money and where I decided to spend a little more than usual!

One of my friends was awesome and got me the Chicago CityPASS, you definitely want to pick it up as there are several packages, this one covered all my museum visits, and of course the must do in Chicago the visit to the top of the Willis Tower.
Luckily summer was several months away because my diet fell off the wagon like a case of booze during prohibition, deep dish pizza, and Italian beef sandwich are must eats. Make sure you request the sandwich wet. I will say for the deep dish I ate at 3 places Pizzeria Uno which reminded me of my childhood at the one in Brooklyn which tasted exactly the same, Lou Malnati's which tasted exactly the same as the one in Phoenix, and Giordano's which tasted exactly the same as Uno's and Giordano's. I'm not knocking any of these, they were all delicious, but what I am saying is don't worry too much over which one you pick. It will be a great pie any which way.

Night life does not stop in minus what feels like 50 degree weather. Every night there is a bar or club to find great drinks, dancing and people after you ate too much pizza.
By going off peak season I saved a ton on the hotel, and yes hotel! I rarely book hotels but The River Hotel was significantly cheaper than Airbnb, had a gym, laundry, and free coffee/cappuccino/snack bar at only $75 a night! It's over $250 a night in peak season!
Another benefit of peak season I had heard from my friends for years about the shopping/visitor area Navy Pier, it's one thing to go when everyone is there but it was also such a unique and completely free experience to go there and be the only guy standing there, breathing in the cold air and admiring the beauty of the frozen lake Michigan in front of me.
Of course visiting most place over New Year's will have some great Christmas sightings and decor as well for free. I stopped by the good old bean this day and later their big Christmas tree.
Touring the museums, eating the great food, drinking too much at night, and seeing the famous places were all great, but to finish out 2017 I wanted to do something really special, so to splurge on the trip December 31st I took my first flight lesson for about $300. I went through Windy City Aviation and did everything except land! I had originally not wanted to do it on the 31st to not screw over the pilot's holiday but cold weather rescheduled us and he said it worked out better for him anyway, I gave a good tip too of course. The photos will not explain the feeling of flying over downtown Chicago and seeing this beautiful city on the last day of the year. Needless to say money very well spent!

And last but certainly not least, anyone who has been in my house knows my all time favorite painting in this world is The Old Guitarist by Pablo Picasso 1904. A replica hangs in my living room and it had been my dream for over 20 years to see it in person. That dream became a reality the same morning of my flight. It was bigger than I expected both in size and in awe it struck on me. I had 2 hours or so to spend in the museum and spent 30 minutes on one painting out of the thousands there. To be able to see the fine details of the strokes, to feel the sadness of the blue period, see the hidden painting underneath which doesn't show in photos, and feel the spirit of Picasso himself right there was like no other art experience in my life. 2018 would bring so much into my life, what a great way to start it.