Chicago in November- restaurants

Depending on when your trip is, you might want to visit the Christkindlmarket, which has lots of interesting shopping and snacks, and is very close to the Art Institute. It will be open November 16 through Christmas Eve.

I think there is also a smaller one in Naperville.

I used to live in Naperville. I miss it.
Assuming you’ll be downtown (Anderson’s Bookstore?), and you have time for a meal there, some of my favorite places were Sullivan’s (Steak House), La Sorella di Francesca (Italian), Ted’s Montana Grill (Burgers), Quigley’s (Irish Pub), and Catch 35 (Seafood).

Chicago has several Michelin rated restaurants. They generally aren’t my favorite either, but the one I would unreservedly recommend is Topolobampo. It’s a Bayless restaurant, adjacent to Frontera, but it’s food is totally different. High-end, elegant Mexican instead of stereotypical Mexican. It’s the best restaurant in Chicago IMHO.

We have a lot of molecular gastronomy places, Alinea, Next, Blackbird, Schwa, Oriole etc. It’s an experience, but I wouldn’t recommend it to you based on your previous comments. My favorite in that ecosystem is Boka…they dial back the experimentation a lot and provide you with a proper meal while still providing something new.

Steakhouses are king in Chicago and everyone has their favorite. A few have been mentioned here. I personally enjoyed Roka Akor a lot, it’s a little bit different spin on it with Japanese influences and without the white tablecloths. It’s a small chain, but still great. I also liked Swift and Sons for a more traditional, but not stodgy, vibe.

For reference, 8 blocks = 1 mile in Chicago’s grid. That gives you a lot of options. Also consider an Uber/Lyft. I wouldn’t let the $5 ride steer you away from the great places in Fulton Market, North Halsted and River North.

Being on the older side, do you have any aversion to higher-energy, trendy spots? the popular places in downtown Chicago can feel like a bit of a scene. Depending on when you’re dining, especially on a Sunday, you may be able to avoid most of that even at the trendy spots, but worth thinking about.

Shopping is getting trickier these days with the retail apocalypse. Most of the central shopping districts are dominated by big chains. Michigan Avenue, State Street and Weed Street are all the same brands you’d find at any high-end mall these days. Lincoln Park (Armitage), Roscoe Village (Southport) and Bucktown (Damen) are heading the same way, or else they have a lot of empty spots where cute boutiques used to be. West Loop/Fulton isn’t really known for shopping, unless I’m out of the loop. Maybe someone else in the thread can do better on that topic.

Food wise, there are infinite possibilities. We literally have everything if you’re not limited by budget and/or atmosphere. If you’re strictly looking for walkable options, that’ll be your biggest limiting factor. Unfortunately my adventuring days are in the past, so those secret hidden gems I won’t know.

Sounds like a full day. Couple other ideas to consider, the museum campus gives you a lot of variety and is just a damn pretty view of the city if the Art Institute feels starts feeling stifling. The Chicago Architectural Society is close by on Wacker and does some good walking tours (short, slow pace) and boat tours on the river. Chicago is famous for it’s architecture after all. Just to reiterate, think about using Uber/Lyft. It’s cheap and really expands your options/while saving time.

As I’m sure you’re aware, Naperville isn’t really on the way to Rockford…but not that far out of the way either. If the weather holds up, the riverwalk in Naperville is a nice spot to relax and have a snack.

I love the Museum of Science and Industry. Hands down, my favorite in the city. But the Christmas Tree exhibit is underwhelming IMHO. Depending on when your flight is and when you get on the road that morning, the logistics there may be really tough. Rockford to Hyde Park via car, during morning rush will probably be 2-3 hours. Then Hyde Park to O’Hare in a car will be at least 60 minutes if there’s any traffic at all, and afternoon rush can start pretty early on a Thursday. It’s probably doable, but you ma be in the car more than you’ll be in the museum.

Let me know what day you’re going to the Art Institute. If it works with my schedule, I can get you in free since I’m a member there. You won’t have to hang around with me, I’m on a quest to visit every gallery at the museum by year’s end.