Go to the Beach

Ok so this one is a bit of a no-brainer, but just in case. Everyone should go to the beach at least once during the summer. It's pretty easy to find and get to, I mean c'mon. I personally prefer Oak Street Beach, because it is pretty clean and not too crowded, also it gets some decent waves. Go forth, explore the sandy dunes.

Movies in the Parks

The Chicago Park District does this great thing where, during the summer and early fall, they show movies outdoors. They show different movies at a multitude of parks, some of which can be really close to you. Best of all, it's FREE. The full list of scheduled movies is on their website. So grab some friends, sleeping bags, blankets, and sit back and enjoy the show.

Flash Mob!

One advantage of living in a large city is that there are a lot of public places. What better thing is there to do in a public place than a flash mob. It doesn't necessarily have to be an elaborate choreographed dance, it can be as simple as a pillow fight. I'm providing a link to a how to guide for flash mobs.
Go Forth!

Geocaching

This is something that you can do anywhere, and I'm pretty upset more people don't know about it. The geocaching website describes it as a "real-world outdoor treasure hunting game". Basically you punch in a zip code and it will give you different caches in your area.

While some require you to be a member, there are plenty you can do for free. Usually the caches are small black containers with paper in them to write your name. Well what are you waiting for visit their website and join the fun.

Year Round Ice-Skating

One place I always love to go, no matter the weather, is McFetridge Ice Rink. Located at Irving & California, it isn't too far and easily accessible via CTA. It is a great way to let loose with your friends. Honestly who doesn't enjoy watching your friends struggle on the slippery rink?

It's relatively cheap as well, cheaper than a movie. I costs $8 if you don't have skates, and $5 if you do. They have a few different open skate times, the weekend ones are more popular. To find skate times click here and scroll down to Public [Open] Skate Times. 

I'll post some pictures of my next visit.

Go forth, explore, have fun.