Dude, Rosemont is like 3 min away from ORD and prolly has more hotels/motels than any other city near Chicago... Im sure u can find some decent place.
What to do there? i dunno, depending on what u like doing )))))
what do u usually do with ur free time?

 

You could always go to Six Flags in Gurnee.

 

Rush St has some cool bars.

 

Haha, my spare time is usually spent doing school work... Otherwise, I'm a cyclist. I spend lots of free time on the bike. Not going to be doing that in Chicago, lol.

I will probably just tour around... Keep it unstructured. The zoo and boat tours sounds good. So does deep dish pizza.

 

I never see you there

 

Spiel, dude I have never seen u there ))))))))
when are u finally gonna show up ))
any DJ events coming up?

 

OP, i dunno then... you can go to the Botanical Garden LOOOOOOOL
seriously, if you are gonna be alone, than there is not much to do...
Sears Tower is pretty cool though, you can see a lot from a 99th floor

 

I'll be there with my girlfriend! Haha the botanical garden could happen... Hahaha

I think the boat tour, rose shaped tower (?) and wandering the streets will be adequate. This trip is pretty casual with absolutely no structure other than on the tuesday... so I'll be free to wing it.

 

I'm planning a trip to Chicago just like this with a girl friend... though just a friend. We were going to do it last weekend but decided to wait till we had money again haha. Who know's might end up being similar date lol

 

They got that tour bus (with no roof) thru the whole DOwnTOwn... people seem to be enjoying it ))
U can also go to Montrose Beach in downtown...
If u wanna go to some bars, go to Depaul Univ. area.