Trip update. Decided to go with the Uber from the airport to the hotel (just easier), after getting in 30 min early on our flight, which was nice. After checking in, went for our first meal to the original Billy Goats a few blocks away under Michigan Ave and had a dog and a burger - yum. Wife thought the burger was just ok.
Then it was off to a walk around the river area by Michigan just to see the sights and then we went to the Chicago Architecture Center, which was very cool. Their current exhibit is all about engineered timber products for construction, showing how it's made and the various uses in major buildings around the world, including skyscrapers up to about 50 stories so far. Plus they have the permanent section showing the scale down version of every major building in Chicago among other things.
After a little shopping and resting up, we took the walk out to the French inspired Bavette's Bar & Boeuf, as several of you recommended, Huge thanks from the wife and me, as we both thought the meal and the ambience were in our top 5 all-time, which is saying something for us, as we probably eat out 4-5 nights a week (and always have). Couldn't get a reservation, so we took a chance on getting bar seating and got seats within about 20 minutes, which was great. Also, the walk down Hubbard St. in particular, was great, as there were tons of people out and about, as there are so many interesting/cool looking bars and restaurants along several blocks (might want to visit a few of those).
Had a great couple of gin and tonics and then we had apps: I had the shrimp cocktail, which was superb, as the cocktail sauce was perfect, but even better was the Dijonnaise, while my wife had the wedge salad which she loved. Then the star of the show, as I had the classic ribeye (my favorite cut, usually - I love the marbling/fat/flavor of the ribeye over leaner cuts) and my wife had the filet mignon and both were great, especially with their phenomenal Bearnaise sauce and "steak salt" (and even the fries with the garlic aioli dipping sauce were great). The bar was seriously cool and we dug the low key jazzy music and we ended up chit-chatting and joking around with several others sitting at the bar, which is not something that happens at a table. We might even go back before we leave, as it was that good.
Today's activities started off with a walk down Michigan Ave towards Millenium Park and the Chicago Art Institute, with a stop at Sweet Water for lunch. Nothing spectacular but very solid Buffalo wings and pretzel bites for me while the wife had a grilled chicken dish she enjoyed. I knew my wife would love the park and the museum and she did. Took our time walking around most sections of the park, taking lots of pictures (she has showed her photography at art shows in the Metuchen area for many years and has curated a local Metuchen gallery for about 15 years).
And we had a good 3+ hours for the museum, which is way more than the ~1 hour I had 2 years ago. Were able to leisurely go through the entire Impressionist wing, as well as the Modern Art wing (our two favorite art "types"), both of which are filled with amazing works from the best ever. And
@SkilletHead2 will be happy that we found all of the paintings he recommended - and it turned out these made up about 2/3 of the paintings I took pix of 2 years ago, lol (I just didn't know all the titles).
We also spent some time in the currently running feature exhibit of work from Camille Claudel the famous French sculptor who studied under Rodin (in more ways than one, lol) and eventually became his equal, prior to kind of losing it and being committed by her family for her last ~40 years which is very sad. We both were huge fans of the French film bearing her name which came out in 1988 and was instrumental in getting the art world to pay attention to her accomplishments more.
After resting up for awhile (lots of walking tires out old folks, lol), we went to Joe's Seafood for dinner, as we have been to the one in DC and both really enjoyed it. Another great meal was had. I had the octupus with Kalamata olives app and the sauteed scallops entree, both of which were fantastic, along with another side of fabulous fries, while my wife had a roasted garlic and lemon chicken that was absolutely delicious. We also had scrumptious desserts: Key lime pie for her (this place makes the best one she's ever had and it's her go-to dessert) and a fudge and cream concoction for me that was yummy.
Probably the architectural boat tour and maybe the 606 rail line converted to a park; haven't selected a dinner place yet (I'm interested in Torchio as I love top end Italian).