petlovr, we did quite a bit of walking on the day we did the American Writers Museum, Eataly, and then shopped The Magnificent Mile all the way to the Hancock Tower/360, Billy Goat Tavern, and back to hotel. I don't know the mileage/ steps (should've checked the seven year old granddaughter's Fitbit....lol), but I was pretty pooped when the day was over. On day 2, we walked to Millenium Park and The Art Institute but it wasn't that far from our hotel on West Illinois Street. Your traveling partner with foot problems may have a challenge, though, unless you enlist the help of a cab or Uber. Since our daughter did the Uber contacting/negotiations using her phone app, I don't know the exact costs of those rides, but it seems she paid @ $12-15 for all five of us to get around to places like the Field Museum from hotel or to Navy Pier from The Art Institute per ride. I perceived it as a real bargain at the time;). If I were you, I would just plan to budget a little more for such. I don't know your method of travel, but I assume you're driving. As you know, parking is a hefty price, but so is transportation to/from airport. We flew Southwest to Midway and paid @ $70. each way. Maybe that's why I thought those short Uber rides were such a good deal...lol.
Re: New Orleans .... I remember a visit several (probably five) years ago during which we were with jlr and some other TA friends...she made sure to take some pics to share with you. (My DH says my memory is bound to be a sign of psychosis...lol).