When using a simple optical telescope to look at the night sky, you could just point at random objects and locations to see what you could see, but you would probably see a lot more interesting things if you planned ahead. To plan, you would need to select an interesting object that would be in the sky on the night you will be observing.
For a summer observation, research objects from the following list: Messier 13, Messier 27, Messier 51, Messier 64, Messier 82, Messier 94, Messier 102, NGC 40, NGC 6543
For a fall observation, research objects from the following list: Messier 57, Messier 27, Messier 82, Messier 33, Messier 51, Messier 13, NGC 869, Messier 1, NGC 6888, NGC 6992, NGC 7293, NGC 7635, Messier 102, Messier 81, Messier 31, NGC 6543
Alternatively, to plan, you could look on a sky map or use software to find out what would be in the sky on the night of your observation. These tools can show the night sky at a particular latitude (Iowa City is about latitude 40°) during a particular time of the year. You would need to do some checks to make sure that the objects will be visible with the specifications and restrictions of your particular telescope.
The Univeristy of Iowa RST Calculator (Rise/Set Time Calculator) will be helpful for learning which objects are up in the sky at the time you are interested in observing. At the page linked, click the RST Calculator icon. A window will pop up that will have you input the Univeristy of Iowa observatory you are interested in (Van Allen Observatory) as well as the object and date you are intersted in. Then click 'Calculate'.
The RST Calculator will output the RA and Dec of the target. When the target is above the horizon, the tool will list the elevation (altitude) of the object throughout the night at 1-hour intervals. This is useful, as the best time to view an object is when it is at the largest possible altitude above the horizon, so the target is being looked at through as little atmosphere as possible. The times of these elevations are given in 24-hour CST/CDT (central) time as well as in UT (universal time, the time in Greenwich, England).