Current Case undergrad and more than happy to answer questions about the city! I'm from Chicago, so my perspective is coming from a large city. Because of its higher prominence in the 20th century, Cleveland has a lot of amenities given its size and population. I'm also a senior, so I've spent the last 4 years really being able to explore and getting to know the city. Just in last summer and September, I was able to go to several professional NBA, NFL, and MLB games; a national premiere for a play, along with several other professional productions; an airshow with some of the best aerobatics pilots in the country; concerts for some of my favorite bands (most recent was Glass Animals); kayaking on Lake Erie and trail running/gravel cycling in a national park; very popular Greek and Italian cultural festivals with great food around the Feast of Assumption; several film premieres in a historic theater south of campus; concerts held by one of the best orchestras in the country, including a fantastic performance at a really cool
summer music festival; and just a bunch of really cool farmer's markets in the fall and summer, along with some other random events. I was able to experience all of this in just a few months, almost entirely relying on public transportation and a bike (I'm an avid cyclist). If you have a car, that opens up a lot of other things including visiting Cedar Point if you're an amusement park fan and anything in Pittsburgh.
I'm also very experienced with a lot of different neighborhoods and their history (it's part of my nonprofit work). One of the biggest issues with Case's undergrads (I'm not sure if this completely applies to the med school students, but it probably does to a degree), is that people don't frequently go beyond a 1-2 mile radius around campus and/or aren't on campus around the summertime, which is when a lot of thing happen in Cleveland. This leads to a skewed perspective that there isn't a lot to do in Cleveland, which I 100% disagree with.
Nightlife is good; if you're not a college freshman, the bar and nightlife scenes are strongest in (in decreasing proximity to campus): Little Italy, Coventry, Shaker Square, East 4th St, Downtown, Tremont, the Flats, and Lakewood.