My wife and I are both seniors and are planning a trip to Chicago.
Any comments on the Fairmont or Drake Hotel would be appreciated.

They're both nice properties, in my opinion. It sort of depends on what you're looking for. The Drake is at the north end of Michigan Avenue and so the Magnificent Mile, with all its shopping, is right outside your door. Lookingglass (highly recommended) and Drury Lane theaters are right nearby. Lots of restaurant choices in the area and Oak Street Beach is in front of the hotel.

The Fairmont is a newer (though not new anymore) property south of the river. It sort of positioned between Michigan Avenue and Navy Pier (using typical tourist attractions as my bookends there). Millennium Park, Grant Park and the Art Institute are nearby, as is the Cultural Center, theater district, etc.

I like both hotels and in terms of accommodations, you can't really go wrong. A lot depends on what you want to do while in the area.

Thank you so much for the good info.
What is the best way to get to hotel from
Midway? Thanks.

Orange line on the CTA will take you into the Loop. But taxi is easier and if you are choosing the Drake or the Fairmont, I'm guessing you're not doing the trip on a shoestring so the taxi fare won't faze you. Assumptions abound!

Thank you so much for the input. I have decided to take
a shuttle from Midway to The Drake. I hope it turns out
to be a good choice.