A couple of recommendations since you are in Ukraine Village. The Empty Bottle is nearby. That is one of my favorite venues for live shows. Small, good vibe. For food, Fatso’s Last Stand. Awesome food. If you want to do a Chicago Hot Dog, they have a great one and their burgers are outstanding.
Here are some random recommendations for the rest of the city that are popping in my head:
Music Stores:
Chicago Music Exchange - Huge music store. Lots of instruments to play. Right by Reverb headquarters as well. The owner of Chicago Music Exchange actually started Reverb.
Rock N’ Roll Vintage - This place is a bit smaller, but has a nice synth/modular section.
Music:
Green Mill - My favorite jazz club. Supposedly it was owned by Capone’s right-hand man. When you walk in you feel like you are walking into a club from that era.
Coles - Good vibe, have seen many good bands here in the past.
Cocktail Bars:
Whistler - Chill Vibe, can get busy, but often has good live music or DJ’s.
The Violet Hour - Interesting place, amazing cocktails, just needs to be experienced.
Breweries - too many to count, but here are a few:
Dovetail - One of my favorites, with a focus on German and European style beers. They are doing an Okterberfest thing Sat. and Sun. with Begyle Brewing that is right next door to them. They basically close off the street between them, have bands play outside and food trucks.
Half Acre - Awesome Beers
Revoution - Aweosome Beers and Food.
Goose Island - Well worth the visit. They have some really creative beers that you don’t find in the stores. And a few years ago they redid the whole interior/taproom and it is huge and really nice.
Lagunita’s - Obviously not originally from Chicago, but the atmosphere is worth the trek. They built the whole thing into an old warehouse. Cool place.
If you are downtown, the area of Millenium Park/Grant Park can be very beautiful this time of year with the colors on the leaves starting the change. The Art Institute is also nearby, which is a worth the visit alone. And there ain’t no shame in the game of getting a picture near the “Bean”. I often bring people down to this area when they are visiting, it is very nice.
Also, the river walk is very nice. They completed that a couple years ago. And along the river is the “Art on the Mart”, where art is projected onto the Merchandise Mart building in the evening, probably sometime around 7-9pm, but check the times to be sure. If you are already down that way it is pretty cool.
Too much great food to list, all over the city. Both Au Cheval and Loyalist have amazing burgers, and are often listed on the “best-burger” lists. Both are in the vicinity of Fullton Market area, which is a great area for food and drink. Haymarket Brewing is also in the vicinity. But again, you will find great eats and drinks all over the city, and I am sure your wife’s friend has a handle on that. Same goes for neighborhood bars. Lot’s of great ones, and I am sure your people with have good recommendations.
For field recordings, just ride the train around, that’s what I do. Lots of sounds to record and experience in the city. There is construction outside my window today and I grabbed a snippet of that.
And for records, I always enjoyed Reckless Records. There are a few of them around the city.