Evening Events in Chicago

I have shared a couple of day activities that I got up to when I was in Chicago but I don’t want you to think I was boring sitting in every night, so I’ve added all the evening events in one post to show that there’s something for everyone’s taste. Chicago is known for their Jazz clubs and improv comedy so of course these made my list and being a spots fan, it’s always nice to experience cultural sports.


If you’re a ports fan, Chicago is a great city. They do well in most sports and even hosted the 2016 NFL Draft. I saw them setting up the stage and Ferris wheel in the park when I was there, and how crazy the traffic got when it was on.

Anyway, we originally looked at tickets for the ice hockey as Chicago Blackhawks had made the playoffs but they’re far too expensive so we settled for baseball instead. Apart from American Football it’s probably one of the most American sports around.

Cubs game

Chicago has two teams, The white Socks and The Cubs. The White Socks is the team that does well and The Cubs always struggle. The White Socks was playing away all week during my visit so we went to see The Cubs to see them play at their home arena, Wrigley Field. I got there a bit earlier so stopped for a beer at the next door pub where the atmosphere was intense. They’ve got some dedicated fans, which is nice to see.

The arena wasn’t full, but I don’t blame people, it was a cold and windy night so sitting still isn’t very pleasant but we did fine dressed warm and enjoying some more beers. The game was a bit slow to start with and I had to get a recap of the rules as I’ve not watched a game in 15 or so years. Cubs won in the end with some decent innings: players on every base and finally a home run or two as well.

Jazz Club

If you’re a music fan, you need to visit a Jazz Club. If you’re not a music fan, you need to visit a Jazz Club in Chicago. We went to Green Mill (don’t be discourage by their website), which used to be one of Al Capone’s favourites. He had his own seat, apparently the one where you can see all exit doors, and always drank gin and tonic so of course we did the same.

The band for the night was amazing! At a first glance, possible the most miss matched people put together but oh so talented and they played and sang really well. I’ve never heard jazz live before, nor do I listen to it on a regular basis so I can’t compare much but I really enjoyed the evening and so did the rest of the crowd.

Green Mill

When we arrived, half the place was full but in time for the band to start playing, it was a full house. We went on a week day so if you’re planning to go during the weekend, be prepared to possibly having to queue outside for a seat. You’ll also be asked to stay quiet during the performance so if that’s not to your taste, head somewhere else.

Improv Comedy

Just like Jazz Clubs, improv comedy is another cultural activity which Chicago is known for. I didn’t know this prior to my visit so it was really nice when my friends suggested we’d go. We went to The iO Theatre, apparently Chicago’s best improv theatre but also the home of improv comedy classes. A lot of people who want to get into the industry start in Chicago and the walls were decked out with lots of famous (not all to me) comedians’ head shots.

Anyway, the play we went to see is performed by a group who focuses on Shakespeare improv, all their plays are performed in true Elizabethan style and all shows are improvised, never being the same as the previous one. Once seated, the group came out to explain how it works: the audience give a name to the play and based on that the actors play out a Shakespearean comedy in two acts. Ours was named “Don’t Scratch my Nose” and we got to see the opening night and closing night all in one.

iO Theatre Chicago

I can’t remember when I laughed so hard last time. I was so impressed with them coming up with so many spontaneously jokes, creating a story and making sure none of the parts were rushed in order to fit in to the time given and how well (not all the time) they managed to keep a straight face. You can check out a video here with a teaser of how it works here.

If Shakespeare isn’t your thing, The iO Theatre has many other concepts and layouts of improv to choose from.

Have you been to any similar events? What do you like to do for evening fun when you’re on holiday?

Jennie xx