Hello!

I am going to Chicago for a week and would like to have some good meals, but want to be comfortable dining as one. Are there any restaurants that are better to eat alone than other?

Any suggestions?

I did this often when I travelled on business. Apart from the obviously romantic places, I don't see why you shouldn't enjoy your meal wherever you go. It all depends on your attitude. If you are uncomfortable, I suggest you bring a magazine or book and request a table with decent light. I was never allowed to read at the table as a child so it remains a guilty pleasure for me!
Sorry I can't give you any specific restaurant recommendations, but this reply will at least top your message.

ttt

I ate alone at Everest and was very well-treated by the waitstaff - never got bored, even without a book. The nice view helped. This is not a place most people think of for eating on your own, more a place to impress others or have a celebration.

Not sure what you have in mind but there are several restaurants where you would not be uncomfortable eating alone. If it was me, I would be more comfortable at the more casual places like Cheesecake Factory, California Pizza Kitchen, Heaven on Seaven (Cajun food), Star of Siam. However, Chicago has many business travellers that eat alone and you should be comfortable any more you go.

You might also post or search on chowhound.com and egullet.com.