A Long Weekend In Chicago

You know how there are some trips that you plan that you just can’t stop thinking about? How you endlessly peruse Pinterest and scour other travel blogs to find the best things to do? I’ve had my share of those trips in the past, but Chicago was totally not one for me. I was excited about traveling with/to some friends but, all in all, the trip just snuck up on me. Blame it on the destination or the grad school, whichever you prefer. Either way, I was just not SUPERPUMPED about Chicago. And I am a SUPERPUMPED kinda gal. However.

Chicago totally surprised me! I am not saying it has moved its way onto my “To Move” list (uh, hey, winter in the city blows), but I was impressed nonetheless.

So what impressed me?

The Food


As with any trip, I spent most of my time eating food in Chicago. It was to the point that I felt like I needed to be rolled onto my plane home. Ice cream, popcorn, deep dish, hot dog, beer, coffee. Check, check, check, check, check, check. Plus about a billion other things. My verdict on deep dish: it is very delicious, but I can only have one piece. Man, that dough fills you UP. But anything with a mass amount of cheese on it is okay in my book.

Chicago Hot Dog

It seems silly, but my favorite place was this bar we went on the last night. It had a bucket full of menus that you could order in from. And the bar was full of board games. It was just perfect, especially after three days of running around non-stop.

The. Public. Transportation.

I know. Who gets pumped over public transportation? Somebody who lives in a world with extremely frustrating public transportation gets pumped. Ayo, Septa. I’m talking to you. If you’re visiting Chicago for a couple of days and you are coming in from one of the airports, totally invest in a 7 day pass. The Blue Line to the city by itself is $5. And usually I am all for walking everywhere and saving a bit of cash, but do you know how big Chicago is? Public transportation is the bomb.

Plus you get this cool credit card-type thing. And you just tap and go. Badabing, badaboom. Even if you don’t get the pass, the card is easily rechargeable. No buying 3509746 tokens that smell like they’ve been peed on. Philly. Get your act together.

Lake Michigan

Chicago Beach

Are we sure this isn’t just a mini ocean? There are mini beaches. Are we positive? One of the most fun things we did in Chicago was rent bikes and just ride along the lake. You can ride for forever! Or something like 20 miles at least. We stopped by Lakeshore Bikes to pick up our rides. If you're in their area, I couldn't recommend them more! Super awesome to work with. And they are an actual bike shop too. Philadelphia bike shops: open one on the trail...why haven't we thought of this yet?

Chicago Biking

We rode down to the Lincoln Park Zoo, Millennium Park, and then continued on to where all of the museums are. Because we locked up our bikes and got lunch near Millennium Park, we had to turn around then. But it was just such an awesome day. Even if we got absolutely soaked with rain.

Chicago Bean

Chicagoans are Funny

At least, funny people flock to Chicago. Have you heard of The Second City? Even if you think you haven’t, you have. This comedy club produces just about the most famous funny folk ever. Seriously. Take a look at their Wikipedia page and just bask in the alumni. If you are in Chicago, spend some dough to see an improv show. HILARITY will ensue. I almost wish I took video against their wishes and got thrown out, just to show you how funny it is. But then I wouldn’t have seen the rest of the show. So just go yourself.

That Chicago Skyline


I flew back into Philadelphia and wanted to CRY when I saw the skyline. That’s it?? Chicago’s skyline is SO COOL. If you go to the Lincoln Park zoo, they actually have a pretty cool plaque that names all of the buildings and gives you a little blurb about them. I am not even into architecture, but those river cruises? Awesome. Even if there are hundreds of school-age children on board.

Chicago Skyline

You know those pictures where people take pictures in glass boxes? Yeah, that’s the Sears Tower/Willis Tower. Depends on who you talk to. If you want to go all Ferris Beuller and check it out (along with a zillion other people), totally do it. I’ll be jealous of your picture. Instead, we went up in the John Hancock Center. There’s a bar up there, so you can sip your drink and just stare outside. It’s an awesome experience.



Chicago is a pretty awesome city, and I would love to go back. It is easy to think that you could see yourself living in a place like Chicago, especially if you visit on a sunny day. Even when we visited the last weekend in May, though, the “feels-like” was 38 degrees one day. THIRTY-EIGHT DEGREES. Granted, they were going through a cold snap. But I would hate to see myself there in February when 38 degrees feels like a summer vacation.


But I guess never say never?

Have you ever been to Chicago? What was your favorite part? Do you think normal people can stand that cold or just superheroes? Or option C: I am a weenie.

A note: I went on this trip with about 9 people. All of these pictures are either mine or Paul's. For the most part, I stuck to pictures of us just so nobody would get antsy about being on a blog. If you all want your beautiful faces on here and stumble across this, just let me know! And sorry, Rachel. Our picture is too great to ignore.