I second the view when entering the city on 376 West.
So many nice hotels in Pittsburgh. There are several Downtown, as well as a few more on the North Shore/North Side, a quick walk across the Allegheny. The Warhol Museum is over there, as are PNC Park (Pittsburgh Pirates), Heinz Field (Steelers), Mexican War Streets, Randyland, the Aviary, and lots of restaurants and bars. I love North Shore Tavern (try the “Steak on a Stone”).
It’s an incredibly walkable city. Look into https://trustarts.org/ if you’re interested in musicals, etc. - our theaters are gorgeous, and the whole Cultural District is full of cool bars and restaurants, including Meat & Potatoes, mentioned above. I love Condado Tacos, Proper Brick Oven & Tap Room, and Nicky’s Thai for dinner, and check out Waffles, InCaffinated for breakfast.
The Strip District (easy walking distance from Downtown) is full of markets with meats, cheeses, veggies, flowers, fish, coffee and tea, etc. The South Side (not easy walking distance) has lots of bars and restaurants, lots of young people and night life. Station Square can be cool, the Grand Concourse is beautiful, and it’s close to the Incline somebody mentioned above, which is absolutely worth it and will take you up to Mt. Washington, which is a must for the view. Market Square is right downtown and is fun, with merchants or performing artists, etc., depending on the weekend, surrounded by restaurants/bars, and featuring beautiful PPG Place (PPG Place - Wikipedia) and one of a few Primanti Brothers locations (there’s one in the Strip, too). I don’t think that’s necessarily a must-see, but it’s a decent restaurant, and the sandwiches are uniquely “Pittsburgh.” If you really like fries, lots of places here put them on salads, too.
I’m absolutely babbling now. Love Pittsburgh! Feel free to ask for more details about anything.
Oh, I forgot to mention Oakland, where the University of Pittsburgh and Carnegie Mellon University, plus the Carnegie Museums (and lots of other stuff) are. Heinz Memorial Chapel (https://www.heinzchapel.pitt.edu/) is beautiful. The Cathedral of Learning (Cathedral of Learning | Campus Tour) is wonderful, but I’m not sure if they still offer tours.
Lawrenceville is recently trendy, not walking distance from Downtown, but The Church Brew Works is a cool place (https://churchbrew.com/), and my favorite card shop (Wildcard) and a few great breweries are there.
Have fun planning!