All that I’ve ever heard fellow New Yorkers say about Chicago is that they love it. Unequivocally, without hesitation, without even feeling the need to tack on the often obligatory, “but I could never live there”. In fact, I’ve mostly heard, “I would love to move there”, though to be fair to our charmingly-foul city, nobody ever does move.
But the point remains that New Yorkers love Chicago – and with good reason. It is the home of beautiful and varied architecture, charismatic accents, a unique history, and of course, various well-done renditions of foods New Yorkers already love: Hot Dogs, pizza, and sausage.
Additionally, and refreshingly as it were, Chicagoans also seem to love New York. Of the numerous people I met during my brief stay, absolutely all but one had only positive things to say about both New York and New Yorkers. (Disclaimer: I met all of these people in bars and nearly all were men, but not all were drunk so – take that as you will). There was no sense, as there tends to be along the East Coast, of competition; of feeling like one had to choose which city is better. It was uplifting to be honest, and I think, in part because of this sense of camaraderie, I was able to love Chicago that much more.
Trip Background:
I traveled to Chicago with one of my best friends who I’ll call A, though I highly, highly doubt anonymity on this blog is important as nobody but people I know read it. A is currently getting her masters at an Ivy League school in Manhattan and paying for it herself. Therefore this trip is a perfect example of how to travel on a budget that’s tighter than your little sister’s vagina.
A and I had two mutual friends living in Chicago from high school, and she had a few more friends from college also living there. Additionally, my father’s family is originally from there so I have quite a bit of family in the area.Therefore we lucked out in terms of lodging as we were able to stay in a family member's vacant apartment for free. The apartment is on North State Street, so really close to the main drag of the city. If you are booking a hotel, I highly recommend looking for a place in this area. The L is incredibly easy to use, should you want to explore other neighborhoods (Lincoln Park and Wrigleyville, for example) and this is very central location.
We booked a round trip flight for $230 each for Thursday evening. We were going to use a travel engine, but actually Delta.com had the cheapest airfare for a round trip.
It's also important to note that we took this trip in June. Chicago is famous for insanely horrible winters (duh) and what I think is sometimes lost on North easterners is that this means that it also lasts forever. So, make sure to check the weather carefully anytime before about May.
La Guardia has the most flights between cities, and therefore the cheapest. However, flights to Chicago DO NOT LEAVE out of the main terminal in La Guardia. Instead, you have to take a shuttle to a tiny, bizarre, old terminal that only houses flights to Chicago – so plan extra time for traveling. However, this little freak terminal does minimize time spent in security, so that’s a plus. Returning flights come into the same terminal, and though there is a cab line, we had a later flight home and I had to wait about 20 min for a cab as they were sparse, which blew.
Also to keep in mind with Chicago flights: O'Hare has the highest number of delayed flights in the country. So that also happened, and that also blew.
