Chicago has been on my bucket list for a while. I was actually supposed to go in July of 2020 to see the Rays play the Cubs, however a global pandemic and no fans at MLB games put a stop to that trip.
So early this year when Southwest was offering their annual birthday sale, one of my favorite travel buddies reached out and said “Where should we go?” Chicago was an easy choice considering neither of us has been and it would be an easy long weekend trip.
It has finally come to Chicago week, we leave Friday morning and come back Sunday night. So while it is a short trip we have it loaded with fun.
Here are some of the highlights.
Second City Show
Hands down the event I am most excited for. So many famous comedians and SNL cast members have come through these doors. From someone who loves live shows and comedy I am so excited to see the hype around Second City.
Art Institute of Chicago
While I am not super knowledgeable about art, I have been told time after time I need to check out the Art Institute of Chicago. I’ll be sure to do a full review and if I think its worth the $32 admission fee.
Wrigley Tour
It is on my bucket list to go to every MLB stadium. While there will be no baseball it will be fun to visit this iconic field.
Topo Gigio Ristorante
A local Italian restaurant that came highly recommended. I never pass up good Italian food. Will be the perfect comfort food to pair with the cold weather right before our Second City Show.
Cindy’s Rooftop
Another highly recommended spot. Cindy’s Rooftop is a bar and restaurant that overlooks the city with incredible views and tasty drinks.
Riverwalk, Millenium Park, Lake Front Park
As someone who did not grow up in a walkable city I am most looking forward being able to walk all the beautiful public areas in Chicago.