2:00 PM: Luckys and Thrift Stores

Being two very big Food/Travel Network fans, we had decided ahead of time to make a list of places which we’d seen on both Man V. Food and Diners, Drive-Ins, and Dives. In the end, Man v. Food won since one of his Chicago food stops was in Wrigelyville.

Lucky’s (http://www.luckysandwich.com/) has been a Wrigelyville institution since, well only 2004, famous for their giant, French-fry stuffed, melted cheese, sandwiches (see picture left). I couldn’t find a more appetizing picture, but don’t let my bad photography deter you – they are delicious. And, being enormous, they’re incredibly cheap. A and I split a Turkey sandwich and could barely eat any of the additional fries served with. Pitchers of beer here are also really well priced, making our entire meal only $8 each for a huge sandwich and roughly 3 beers a piece.
Feeling nicely buzzed and really full, we walked around Wrigleyville a bit more. North Clark Street, which runs through Wrigleville, is filled with a number of thrift stores full of vintage Cub T Shirts, pins, and witty silk screen shirts. I bought a few souvenirs here, and there was a really good tshirt about Poop that had A and I laughing really hard. Since this is not New York, even touristy crap is relatively cheap and I was able to get a spiffy Cubs T for only $10.

1:30 PM: Wrigleyville and Harry Caray’s Hot Ass

After cooling down, we decide to brave the L and head to Wrigleyville. If you can handle the subway in New York, you can’t fuck it up in Chicago. It’s half the size, twice as clean, and you can actually hear the announcers.
The L travels above ground, which is actually a nice change in the summer. I bet it sucks in the winter. But as a tourist it’s especially nice as it is yet another way to check out the city. As you approach Wrigleyville there are rows of, well I’ll call them townhouses, but they look like beach houses I’ve seen down the Shore. They’re clapboard (in a nice way) with winding stairs that go up the back, and you can tell it’s a neighborhood for young people because the porches are all messy, many have flags, and most have Christmas lights.
We went to the stadium, which sadly was not open, but we saw the bars and apartment buildings that surround the stadium which all use their roofs as more bleachers. No idea what you have to pay to sit there, but either way A and I quickly imagined ourselves living in a building with Cubs seats on our roof and late summer nights getting wasted and watching baseball, only to walk downstairs and pass out.
We also stopped to admire the sort of bizarre statue erected (hah) in honor of Harry Caray. If you don’t know Harry, he was the beloved Cubs announcer, famous for being pretty ridiculous: http://www.ebaumsworld.com/video/watch/985394/

Another warning here – do not touch the Harry Caray statue on a hot day. This might seem intuitive, like sticking your tongue to a flag pole in winter, or not touching a lit stove, but judgment is impaired after a lunch pitcher at Lucky’s (read: I burned the shit out of my arm trying to be funny)

Day One: The Lake, Locals, and Baseball Landmarks

11:00 AM: The Wendella Architectural Tour

A and I wake up early to the most beautiful view of the city. The apartment we’re staying in faces the water and runs right along the canal. Invigorated and slap happy, we set out to go find the most raved about (by people I know) architectural tour in the city.

The Wendella Architectural Tour is only $25 and completely, entirely worth it. I highly recommend doing it early on in your trip as and you’re able to get a good feel of the city's layout from it. Additionally, they offer a really concise and interesting history of the city. There is also, a bar on board. And it goes without saying I think that it’s seriously beautiful out on the water on a nice day.

The only warning I can offer is that it was really hot and sunny out the morning we went and A got swamp ass so bad it went through her sundress. She was thus prohibited from standing up and going to the edge to take better pictures. Also we had to wait for everyone else to exit the boat before she would stand up and then I had to walk behind her until we reached an air conditioned restaurant where she could air out her ass. So, if you're prone to butt sweat, wear something sturdy.

For more information: http://www.wendellaboats.com/experience/riverarchitecturetour.aspx

A Young New Yorker's Introduction to Chicago:

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.