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My wife and I and some friends are all going to be in Chicago for a week or so coming up. None of us have ever spent any significant time there. Wondering if anyone can recommend some things we should check out while we are there, especially musical stuff falling anywhere from performer to purveyors, and from punk to polka. Or just meet somewhere for a beer & such.

Looking forward to it.

Thanks,

Eric

Redhead piano bar... classic cheesy sing along piano bar. Fun loving crowd. Stay for a drink or the whole night. On W Ontario not far from magnificent mile. Doesn't open until after dinner.

Chi brass is a mouthpiece company with great products based in the northern burbs. Ian is a great person too.

I made the pilgrimage to the fine arts building to see the legendary Jacobs teaching studio and later by his house on 8839 S. Normal Ave last time I was there. I probably looked beyond suspicious pulling next to it on the road and grabbing some pictures.

Checkout the calendar for the Grant Park Festival Orchestra. It’s free and right downtown in the beautiful Pritzker Pavilion

Depending on when you're there, there may be a good CSO, or other concert at Ravinia.

Eat Pizza - lots of it :). Anne Sather is a must go to restaurant for breakfast I never miss. The architectural boat tour is a classic activity.

Instrument shops:
-Horn Stash is out in the suburbs in Palitine but probably the best brass retail place in the area (they actually have tubas!).
-If you're into non-brass instruments then Chicago Music Exchange is a must.
-Make an appointment to check out Miles O'Malley's factory on the south side of you can. He makes everything 100% in house and everyone there is great to deal with.

Venues:
Kingston Mines, The Hideout, The Empty Bottle, Schubas, Beat Kitchen, Honky Tonk BBQ, and the Green Mill are some of my favorites.

Food:
-For pizza, My favorite deep dish is Nancy's on Broadway. My favorite tavern style is JB Albertos in Rogers Park.
-Beef, Gyros, Dogs, etc. you can get a decent one pretty much anywhere. Ricobene's on the south side is a favorite of mine.

Hope you enjoy the city!

Horn Stash is a good place, but call before you go to make sure they have a few horns. It's a hassle to get out there, it'll take WAY more time than you think but will.

I say skip the "pizza", whatever that stuff is supposed to be.

Top of the Willis Tower is cool.
Architecture boat tour is neat too.

It's a fun city. Lots of good parts, lots of bad parts. I've never experienced any issues there myself.

Just as with any city, take a peek at the crime map before you go.
Not all tourist attractions in all towns are in safe areas.
As an example, in Memphis they try to make sure that right at Graceland it's safe, but the issue is that immediately north of Graceland and immediately south of Graceland is quite dangerous.
Another example is the very limited number of north-south-east-west streets in New Orleans French quarter into which tourists should venture. Quite a few years ago, we were robbed at gunpoint in New Orleans just one block off of the area that which is the tourist portion of the French quarter. Musicians - who live there - have told me that they had to be careful (after playing gigs) to not get robbed on the way back to their cars.

My brother - a former world traveler - used to say that it's obvious in most any city when you get to the end of where it's safe to walk, and where you should turn around and walk back the other way. That was decades ago. Today, I'm not so sure that it's that obvious anymore.

I saw a joke that someone posted on Facebook a couple of days ago claiming they got shot just looking at a street map of Chicago.

The Chicago Botanical Garden is a beautiful spot, especially right now with most things in bloom. I was a tour guide there in my college years. Managed to sneak a few flowers to convince Sandy to marry me!
Tim

@bloke
Front the The Babylon Bee...

I saw this guy (and a bunch of great Polish bands including an absurdly crazy rock/horn band and a wonderful Polish jazz band, Wu Wu) at a big Polish festival last summer. If you don't want to go up to Milwaukee that's understandable but they're a fantastic show. The trumpet player drank (a little bit tbh) while they played and the old accordionist played subtle spoilers when the other guys were featured, it was a riot and they're still really good.
There's also a link on his site to 24/7 polka. https://www.keithstras.com/confetti-schedule

Both zoos are great, the Field Museum is great, if you're going to be on the northwest side eat at Paterno's. It was an old family owned joint that recently sold, we haven't been there since but their food was always wonderful. If you get a pizza burger get extra sauce, they also have a sausage crust pizza that is remarkably filling and decadent. Don't go to Papa Ray's, ordering from them is half and half ; if you go to there you risk getting stabbed by the teen clientele (the manager is great, you can only do what you can do). Portillo's still seems to be solid, you can get a giant, tasty double cheeseburger, fries and drinks for 13 bucks (10 for a single). It's a really big burger, I'm 6'9" and used to eat like a pack of wolves and it still takes a sit back or two for me to finish their double.

Wynton Marsalis and the CSO Brass Quintet are playing in the first half of June. Downtown Chicago can be rough, I haven't been there since I moved back to Indiana, I think @tofu has written about it recently. You're not going to have the freedoms you're accustomed to in Texas, just saying. It's probably going to kick off again soon now that it's warm.
https://cso.org/concerts-tickets/featur ... =2026%2F27

Yuengling recently expanded to Chicagoland, grab a 12 pack (or a case, I'm not judging ) for your hotel room.

Thanks everyone! Exactly the sorts of suggestions I was hoping to get!

We are staying somewhere near the field museum, so some of that sounds pretty close. Definitely interested in the live music in particular.

Keep’em coming!

Eric

TxTx wrote: Thu May 28, 2026 12:02 am Thanks everyone! Exactly the sorts of suggestions I was hoping to get!

We are staying somewhere near the field museum, so some of that sounds pretty close. Definitely interested in the live music in particular.

Keep’em coming!

Eric

I stayed down in that area when we took the kids to Chicago over spring break. We did take a few Uber rides to get around town (especially when it rained), but it was quite walkable. If you end up in the North Loop at night, as you very well .ight, take an Uber back home.

Side note -- I was completely impressed by how friendly and helpful all the people were in Chicago. Sometimes you don't know what you're going to get in the big cities... But consistently, the people were really great.

Since you're staying near the Field Museum be sure to catch the boat ride between the FM and Navy Pier. It's brief, but fun.
The giant ferris wheel on Navy Pier is a great memory, too, and there's plenty of good walking chow on the pier!
Tim

Al's #1 Italian Beef.

Get it "soaked" with the bread dipped in the gravy.

A coworker just reminded me of Eric Larson’s “Devil in the White City” which is set in Chicago in the 1890s and mentioned that there are two buildings remaining from that world’s fair. Neato.

Go to Al’s, Pizzeria Uno if you can get in. Or go to Al’s twice. Maybe just go to Al’s.

Sorry. Love that place!!

There was a place in Louisville, KY called Lonny’s Taste of Chicago. Lonny was a Chicago transplant and he had the place decked out in Bulls gear and sold authentic Italian beef, Chicago dogs, Polish sausage, etc. Closed a couple years ago but I would always visit when I was in town. Sure, not as legit as actually going to Chicago but I’d trade it for the 10 hour round trip. Miss that place!

i can't speak to the music places, but the Art Institute, The Museum of Science and Industry, and the Brookfield Zoo are all places I've visited in the past and highly recommend. We stayed near The Loop last time ('18) and walked to the Art Institute (outstanding), Grant Park (nice), and the Navy Pier (good) and enjoyed the experience very much.

If you're concerned about the crime in Chicago vs. other places, there are ways to check that out: https://www.bestplaces.net/crime/?city1 ... 2=51714000