People Live Their Whole Lives in Illinois and Somehow Miss These 3 Places

I grew up in Illinois and had the distinct privilege of living in the Windy City proper for more than 10 years. I made it my personal mission to experience the best Chicago had to offer during my time there. While no list will ever be all-encompassing of all the great things to do in Chicago, this condensed list covers three must-visit places in Illinois to add to your bucket list.

1. Old Town School of Folk Music

The Old Town School of Folk Music is one of the most welcoming places in the city. It is, you guessed it, a music school. However, it’s also a top-tier concert venue. While they offer regular weekly classes, they present a rotating lineup of drop-in one-day workshops and events for all ages. Plus, they regularly present concerts and have featured legendary artists like John Prine. Whether you want to try your hand at an instrument, improve your existing skills, or just sit back and enjoy a concert, the Old Town School of Folk Music is a historic Chicago venue that you need to experience.

2. The iO Theater

Chicago is a funny city. It’s produced comedic legends like John Belushi, Jane Lynch, John Mulaney, and so many more. While many get their start at the famed Second City, the iO Theater continues to present some of the best up-and-coming talent. My personal favorite show to catch is Improvised Shakespeare. You’ll have the opportunity to order dinner and drinks while watching Chicago’s up-and-coming talents perform an entirely improvised show in Shakespearean language. It’s a show I’ve been coming back to for years and always bring out-of-town visitors to. Additionally, the iO Theater presents regular and rotating productions, including Improvised Jane Austen, ComedySportz, free shows, and workshops and classes.

3. Cindy's Rooftop

Finally, if you’re looking for ionic Chicago views, Cindy’s Rooftop is the place to be. Located on top of the 13th floor of the Chicago Athletic Association hotel, Cindy’s offers incredible views of Millennium Park. While it is a rooftop, most of the dining area is heated and covered, so you can still enjoy the views during a classic Chicago winter. The rooftop gets extremely busy, so I always recommend having reservations. In addition to signature cocktails, Cindy’s offers brunch, lunch, dinner, and a dessert menu. I always suggest going to Cindy’s before catching a Broadway in Chicago show or after attending one of the many concerts in Millennium Park. Plus, the Chicago Athletic Association hotel itself is so beautiful that it’s worth checking out.  

This list could truly be endless. I’m a lover of all things Chicago, and I truly hope that everyone takes the opportunity to visit these must-visit places in Illinois. From catching a show at the Old Town School of Music to laughing their head off at iO Theater, and ending their night with a drink at Cindy's Rooftop, there is no shortage of unforgettable experiences in the City of Big Shoulders. Feeling inspired? Try planning your own Illinois trip using Only In Your State’s itinerary planner.