5 Reasons to Spend New Year’s in Chicago

by: Rebekah Iliff

Chicago’s blistering cold is enough to send any human into hibernation, or in my case, running to California. But despite my complete disdain for weather much below “60 degrees and sunny” (I have a weather strategy for all business and personal travel that upholds this standard at least 87.5% of the time), my affinity for Chicago around the holidays always seems to thaw my otherwise scrooge-like attitude toward frigid temps.

In no particular order, here are 5 reasons to strongly consider spending New Year’s Eve in Chicago…I know I am.

#1 Affordable and affable

I’m not sure about the rest of the country, but from California (namely L.A. and San Francisco), you can saunter onto an “I feel like a VIP although technically I’m broke this time of year” flight on Virgin America for under $500 round trip. Once you’ve arrived, unlike L.A. or San Francisco (or New York for that matter), you can jump on a quick and painless train ride into the city that very well may drop you within inches of that nice hotel you’ve booked.

Bonus: People are really nice in Chicago. Like, really nice. They smile at you, ask if you’d like an extra cup of coffee on the house, and sometimes – if you smile back – they tell you how pretty you look when only three square inches of your body are visible through your faux fur parka with matching headgear and gloves.

#2 Entrepreneur’s Eve

I have very seriously considered braving the elements for the one-and-only Entrepreneur’s Eve this New Year’s, which is THE place to be for workaholics like me those who like to hang with fellow crazy people innovators.

This annual celebration takes place at the lovely Adler Planetarium with proceeds going to benefit the H Foundation. Double win: you get to feel smart because you’re technically at a museum with a room full of folks who do cool shit and your ticket purchase goes to a support a charity. What could be better than that?

#3 Chicagoans know how to rock-it

There is one major reason Chicago has emerged to the top of the nightclub and bar scene over the past decade. It’s called Rockit Ranch Productions. I worked there for nearly five years, so I’m not biased or anything, but it’s true! So, if hanging out at a club or getting all gussied up for some good eats with a side of “blame it on the alcohol,” then Chicago has options.

#4 Shopping in the New Year

For those of us who believe the antidote to spending money on others is spending money on ourselves, Chicago is just the ticket. If you decide to take it easy on New Year’s Eve, New Year’s Day is your shot to buy all those things you wish someone had bought you for Christmas (but didn’t), so instead, you have to take matters into your own hands.

From the 900 North Michigan Ave. Shops and the Magnificent Mile to the tucked away boutiques in the Gold Coast including celeb fave “emerging fresh meets vintage” Sofia, the windy city will blow your shopaholic mind.

#5 Sports and comedy

Numero uno: If you like to watch football, New Year’s Day is obviously a huge day for you. And what better way to feed your need for pigskin and men in tight pants then to head to a Chicago bar to watch the big game. Chicagoans get crazy when it comes to football. I’ve seen it. Observationally speaking, it looks like a good time.

Numero dos: If you don’t really like to watch football, but want to see something equally as entertaining and oft humiliating (what could be more embarrassing than missing a field goal from twenty feet away?), I bring you “New Year’s Day Hangover Standup Marathon.” Yup, the Second City has really outdone themselves this time. With this particular option, you can get your workout on by simply laughing yourself to near-death.

Rest assured, I will be wearing a burka-like getup to keep the cold at bay, but Chicago for New Year’s is going to be epic.

About the author Rebekah Iliff @Technori
Rebekah Iliff is the Director of Product for AirPR, a technology platform to increase PR performance. Previously, she was the CEO of talkTECH Communications, one of the fastest growing, launch-only PR firms in the US. As co-founder of talkTECH, she created an industry-first methodology for emerging technology companies. In addition to her business roles, Rebekah is a tech startup blogger for The Huffington Post, and a featured columnist for Entrepreneur Magazine’s “Young Entrepreneur.” Rebekah is a mentor for Startup Weekend Bay Area, an instructor for General Assembly San Francisco, and an advisor for startups at Stanford University’s Graduate School of Business and StartX. Rebekah holds a B.A. in Philosophy from Loyola University Chicago, and an M.A. in Organizational Management and Applied Community Psychology from Antioch University at Los Angeles (AULA).

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