Chicago’s Best Kept Secret

Chicago, can be the best city if you visit in the summer!

If you’re going to visit Chicago you have to come in the summer, sure Michigan Ave is also gorgeous during the holidays but unless you enjoy windy cold wet weather the best months are July through September. Chicago’s waterfront offers so many activities including the exclusive play pen which you’ll likely need to charter a yacht for unless you can find friends with a boat! What makes the play pen unique are the breaking walls that surround it, they keep the water calm in that area which allows boats to link up with each other, and often you can find a string of 10-15 boats linked. Yes boating hoping is dangerous but its also like going to a club with 4 floors, each with different music, people and drinks so just make sure not to over due it and you can hope from one boat to the next to fully take it this party on the water!

Street festivals are also part of what makes Chicago the best in the summer, most of them are free but they ask for a suggested donation, I often say I already donated because the vendors on the street inflate their prices so I feel like by me making purchases I am showing my support. Chicago doesn’t allow open liquor except at street festivals so this is really the only place you can walk and sip without being ticketed, and Chicago loves to give out tickets so beware!

Some of my favorite events are:

Do Division, randolph, wicker park, west town, Greek fest - street fests in different neighborhoods

Any weekend out in the Play Pen - July 4th weekend & Chicago boat scene party are especially busy and crazy in the pen

Air & Water Show - best views are from a boat but the play pen is closed for the show so be careful as the waves can be intense in the open water

rooftops - there are many to choose from depending on your musical preference

west loop - restuarants and bars in this area are legit