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