A Lengthy Recount of My Brief Chicago Tour

I printed a map of the United States a few years ago to pinpoint all the places I’ve traveled and, more importantly, remind myself where I’d like to go. My quota for 2013 is looking good so far as I finally (finally!) made it out to California (extremely late and pretty much #TBT-worthy blog post coming in the near future) and Chicago just a few weeks ago.

My friend Nicole and I decided to book a trip to Chicago in part because we’d both always wanted to check it out and also because every person I know who’s visited has had nothing but positive things to say about it. In the end, they were absolutely right.

With the one exception of Spirit Airlines. (Which, I guess, technically isn’t Chicago’s fault, but still, where was the “don’t fly with Spirit” memo before we booked! Sigh.)

Spirit is a budget airline neither of us had heard of before but went with because it was the cheapest (naturally). Oh, what a mistake we made. When we first got to LaGuardia, we learned that Spirit charges $50 EACH WAY for a CARRY-ON bag. You read that right, there’s not only a fee for checked bags but for carry-ons as well. We were livid to have to spend an extra $100 when we hadn’t even left NY! OY. Our flight was then delayed 2 hours so we vowed never again. Flash forward to our return flight and not only was it delayed for 5 hours with spotty-at-best updates, once we boarded and felt a wave of calm wash over us, it got cancelled due to a “plane curfew” at LGA. WTF?! But wait, it gets better. After deplaning and marching our way through the airport back to check in, we were told that not only would Spirit not pay for the hotel we’d most likely have to stay in given it was 11pm, but they were not going to pay the difference in cost of the American Airlines tickets we purchased to get us home the next morning. The icing on the cake, however, was when we found ourselves sleeping on an almost deserted airport floor because we didn’t want to pay for a hotel. It was one of those moments when you’re so deliriously tired and pissed and just want a drink but all the airport bars are closed, that all you can do is search for the most normal place to sleep and take your clothes out of your suitcase and lay them on the floor to make a bed so you aren’t laying on the (presumably) dirty airport carpet! I’m laughing now, but I wasn’t then.


Ok, Nicole may be smiling but that’s just the delirium I was talking about earlier.

I know I just ranted for a whole paragraph, but this tale would not be complete without those bookends. In the end, we made it home alive so I should be grateful and just add it to my list of “Did That Really Happen?!” Vacation Experiences: there’s been tornado warnings and monsoon-like rain in Memphis (coinciding with May 2011’s End of the World pandemonium), the outbreak of Swine Flu while in a Texas airport, a friend needing emergency surgery after a trip to NOLA, the list goes on and on. Maybe it’s me, lol.

But now, back to Chicago. We seriously had a blast and did almost every touristy thing you can think of but also met up with some of my Chicago-based coworkers, which made us feel not-so-touristy. A few things undocumented are a delicious dinner at RPM Italian, numerous rides on the ever reliable CTA “L”, looking at an apartment to get a feel for comparable rent (and the cold hard truth that you get way more bang for your buck in Chi vs NYC), a night of Second City improv and venturing from a fratty-esque strip in Wrigleyville to the chill neighborhood of Wicker Park for great doughnuts at Glazed and Infused.

IMG_2076 We stayed at the Silversmith in The Loop. Great hotel right next to the train. Oh, and you see all that red? The Blackhawks won the Stanley Cup earlier that week so our trip was heavy on the Hawks pride.

IMG_2077Chicago’s iconic Wrigley building. We took the architecture boat tour – if you do one thing in Chicago (besides eat a ton of fattening food) it’s this.
IMG_2080 Beautiful cityIMG_2089 A nice view of Willis Tower.

IMG_2107 Two girls and a bean in Millennium Park. Almost matching outfits unplanned.

IMG_2112While this stadium seemed miniature compared to Citi Field or Yankee Stadium, the stadium seating on the rooftops of adjacent apartment buildings was really cool.

IMG_2115Lake Michigan beachfront. IMG_2116Oprah used to live here.
IMG_2120A stroll through Lincoln Park.
IMG_2123You can’t go to Chicago without having one of two main food groups: hot dogs and deep dish pizza.

IMG_2124Nicole and I weren’t even hungry when we got to Wiener’s Circle but this was definitely the best hot dog we’ve ever had. A tremendous breakfast at Eleven City Diner was to blame for our “lack of appetite.”
IMG_2125My friend Grace told us about a street fair in Logan Square. We got there just as Santah was finishing their set and I have since played both of their albums to death on Spotify. Here 6 second’s worth on my Vine.
IMG_2128Iconic signage
IMG_2130 One of the more touristy things we did was go up to the 103rd floor of the Willis/Sears Tower. It was well worth it because the views were unreal.
More Hancock building action. 
A petrifying unique feature of the 103rd floor is windows that jut out from the side of the building. You’re urged to walk on them and take pictures so as to look like you’re suspended in air. I have never experienced such paralyzing fear and I’m usually not afraid of heights!

IMG_2143Notice Nicole’s sneakered feet being all brave. Mother of God.
IMG_2145Before we left for the airport we had a lunch feast of deep dish pizza. It was delicious … but it wasn’t pizza. When I think of pizza I think of grabbing a slice after a night of drinking or eating a pie of thin-crusted goodness. Chicago may win the hot dog, but New York clearly wins the pizza.

I’m already looking forward to a return trip to Chicago; to explore the outer neighborhoods a bit more and fly anything but Spirit Airlines.


Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s