Weekend Getaway: Chicago

One huge benefit of working in the automotive industry is getting extra holidays off. Martin Luther King Jr. day is one holiday many people do not get off, but I am luck to. So, with a long weekend and Delta Skymiles to spend, I decided to visit a good friend in Chicago!

Flying in the winter months is always risky. Friday night my flight was delayed over 2 hours due to weather. It was not terrible waiting in the airport, however, because I made friends with other stranded passengers at the bar right by my gate. As four of us waited for planes to arrive and de-ice, we chatted and shared some drinks. I finally landed in Chicago around 7:40 pm. After pushing our dinner reservation back for a 3rd time, my friend and I headed out.


This speakeasy is in a suburb of Chicago and is one of the legal ones. We entered through a side door in the building and was greeted by a bouncer. After asking for the “upstairs” section, the bouncer radio’d up to confirm there were seats available. A few minutes later, we were seated at the bar. The atmosphere was very cool. There were high-backed leather chairs, low tables, and chandeliers overhead. Interesting light fixtures included one with a ram’s skull and horns as the base. The cocktails were elaborate and have a higher price tag – which is to be expected for quality cocktails. The staff was friendly and chatted with us as we sipped our drinks. Overall, it was a relaxed environment and an enjoyable evening.

Second City Comedy Theatre

Second City is a famous theater and has produced many famous comedians. People such as John Belushi, Steve Carell, Stephen Colbert, and Tina Fey (to name just a few) have all performed at Second City. We went to see “She The People” and it was fantastic! A group of talented women spent 90 minutes poking fun at some of the ridiculousness that accompanies our patriarchal society. It was enjoyable and sometimes a little too real. After the show there was a photo opportunity with cut outs of famous, powerful women and strong quotes. The building has multiple stages within it so there can be multiple shows going on at once. The bathrooms had plenty of stalls for a quick intermission break. A free coat check was also a nice bonus as the chairs were packed pretty close together and did not leave room for a bulky coat. It was a great experience.


Portillo’s was my last stop before returning to the airport. A staple of Chicago, according to my friend, after the famous deep dish pizza and I can see why! The location we went to was in an old soap factory building so the inside had a real old time feel. There were many things on the menu and it was a bit overwhelming. I decided on the “Italian beef lightly dipped.” The thinly sliced beef came on a crispy roll with a tiny bit of gravy to round it out. My friend also convinced me to get their “cake shake.” This was an amazing shake. They put an actual slice of cake into the mix! This shake was rich and filling. I am so glad I got to check out this place and can understand why it is so popular!

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