Slightly upscale dinner spot inside the loop for grad student?

I'm hoping to treat my gf to a nice dinner over the next month, and I'd like to take my older brother somewhere nice when he comes to visit in May.

While I'm almost strictly a super cheap eats guy, I'm looking for places that have mains in the $20s-30s range (maybe low 40s) and atmospheres that are a bit more upscale/intimate; somewhere a collared shirt + blazer and a dress would fit in well.

I'd appreciate people's recs and reviews to help me choose a place with the right price and vibes. Here are some I quickly pulled out as possibilities from guides but happy to consider others: Theodore Rex, Nancy's Hustle, Late August (15% Rice discount), Navy Blue (10% Rice discount)