Is parking a problem in Uptown, Chicago?

the eastern portion can be tight

Parking can get tricky in Uptown. Using public transit is a good option if it will work for you. That said, if you are willing to pay for parking most commercial streets have some parking. Residential streets tend to be more difficult in the evening when neighborhood residents are home and parked.

Uptown gets very busy. I had to park well outside of the neighborhood once when visiting. Don't expect to find a lot of easily accessible parking here.

There are some parking options but not a lot. Your best bet is to use public transit - the Red Line runs right through the heart of Uptown.