Last year, I embarked on what was to be a once-in-a-lifetime trip to Chicago to take in the sights and sounds and tastes and local culture and history.
Then on my second day in town I came down with a severe case of rotavirus, got so dehydrated I went into shock, and ended up spending a week in the hospital before flying home without having done most of what I went there to do.
So this year, I’m doin’ it again! I’ll be flying out in late April for a four-night stay, and I’ve already got most of the trip planned, but there’s one big difference this time - I’m bringing my 62-year-old mother with me. She missed a different family trip last year because of another medical emergency, and since we had an airline credit in her name I decided to invite her along.
I mostly have the trip planned, since it’s mostly the same stuff I had planned for last year (though I don’t think we’ll be taking in Wrigley Field since she’s not really interested in baseball). We’ll be seeing the museums and a Second City show, taking a river & lake cruise, and eating at a few of the more famous diners and cafes and restaurants. My mother has two requests - she wants to go on a guided bus tour of the city, and she wants to have dinner at a nice Italian place. By “nice” I don’t mean anything Michelin-starred or with a dress code - just a sit-down place with an old-school vibe and classic Italian-American entrees like lasagna or shrimp alfredo or spaghetti bolognese. Ideally in the Loop or accessible from the L, since we won’t be renting a car. For the bus tour I was thinking something history-themed, whether a general Chicago history tour or one of the mob history tours that I see several of on Google.
I’d appreciate any recommendations anyone could offer.
That’s what I was gonna say. Can’t get more old school than that. Apparently now it’s just the Village plus two other restaurants under the same ownership? I don’t know, but that’s what it seems like—I just remember The Italian Village from my days in the Loop, both figuratively and literally.
It’s been years, but I’d enthusiastically recommend the architecture bus/river tour! I’m not particularly an architecture buff, but the city skyline is spectacular from the water, and I learned a lot about the building of Chicago.
I agree with Italian Village. Go to the top floor restaurant which kinda has a Disney vibe in re-creating an Italian village.
If you want something a bit nicer consider Petterinos.
I will say limiting yourself to the Loop is unnecessarily restrictive. West Loop and River North and Mag Mile/Streeterville and Gold Coast have many, many good dining options and they are not far from the Loop (short cab ride).
If the weather is ok (even if cool and you dress warm) the architectural boat tour is always a winner. If the weather is crap (cold and/or rainy) then maybe not so good.
https://geneandgeorgetti.com/an Italian steakhouse. It’s been years but the entire experience was fabulous. The food the service the people watching, it’s a quintessential Chicago experience.
Rosebuds too for classic Italian with several locations in the city and suburbs.
Gene and Georgetti is great but it ain’t cheap. But, if you want old school Italian it is hard to beat. Also, last I was there, I felt I was in mob central. I had zero problems. Dinner was great. Still…(maybe it helped I was dating the niece of the chef at the time).
Rosebuds is a weird mix. There is only one I like…the one in Streeterville. I was told it is different. The company wanted to close it so the staff bought it and kept it open. It is WAY better than all the rest (IMHO). Also, very expensive.
So, you will find several in the city but I think only one is worthwhile and it ain’t cheap.
Gene and Georgetti’s is at least as much a steak house (like if anyone comes to Chicago and specifically wants a steakhouse, that’s where I’d send them, followed maybe by the Chop House and Gibson’s). So if steak is also an interest, this would be a good, if not cheap, bet.
I had totally spaced on Petterino’s, and I’m going to be there tomorrow tonight. That’s a decent place. To be honest, I’m not super excited about most of the Italian in the Loop and surrounding area (well, minus the long-gone Spiaggia, which was a bit more contemporary and Northern Italian), but anyone looking for an old school red sauce Italian place vibe should have a good time and the places mentioned here.
If you like that check out Erie Cafe for old school and Bavette’s Bar & Boeuf for something newer (although they have been around a long time now too…just not as long).
Both are expensive.
I think Gibson’s is over-rated. It’s not bad at all. Just not worth the price. (I was just at Hugo’s Frog Bar a couple weeks ago…shares the same kitchen).
I don’t disagree. Last time I was there or Chop House someone else was paying. I’m more likely to buy an expensive steak and make it at home, but I am interested in that Babette’s joint.