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Tips for Dining, Eating, and Food Shopping in Greater Chicago

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Toscano's on Oakley...anybody remember her?

This place had a BIG place in my chowhound childhood heart. Just north of Blue Island Ave. on the east side of Oakley . My folks ate there in the '40's and '50...we ate there as a family in the 60's an 70's...and she was gone by sometime in the '80's. She was the epitome of Chicago Italian cuisine complete with the LOUD discussions between cooks and waitresses in the kitchen...the wine bottle candles...and the grape cluster made from empty wine bottles over the large corner booth. As a child the meat ravioli was my fav, and the red sauce on everything was glorious. Anybody else remember her?

    11 Replies so Far

    1. Absolutely! My husband and his family used to go there on Sundays for dinner, and then when we became a couple, he and I started our own Toscano routine. We loved their meat gravy, and I remember my sister-in-law loving and trying to duplicate the crostini (toasted slices of bread with a liver spread). My husband's favorite was also the meat ravioli, but he usually ordered the 50-50 ravs and spaghetti. Incidentally, he didn't mourn Toscano's closing too much, because by then he was married to an Italian!

      We both thank you for the memory nudge!

        1. re: GravyNotSauce

          Loved the place...I'm glad someone else shares the fond memories...

          • Sure; the crostini must have been the high point, since that's all that I remember, and I can't recall having any better in Chicago. By the way, if you want to recapture the experience, you might want to try the nearby Bruna's. Not the same kind of cuisine (Emilia-Romagna rather than Tuscan), but a similar ambience (or at least it was several year's ago).

              1. Losti,
                This is a take from a 7th generation Texan....attended a Bears game with two natives of the Windy City. Both from the near Southside. After the game, we went to Toscano's. It was a tradition for my host's family. We drove by the restaurant before parking, and a vision of a black sedan from the 30's - 40's, with tires squealing and machine guns firing, filled my mind with scenes from The Untouchables. Upon entering, my friend went immediately through an opening to the right, into the bar area, and was greeted by a charming woman as if he was a long lost nephew. We were seated and enjoyed a stellar meal. Don't think that we ordered; the food simply appeared. It was one of the most memorable dining experiences of my life. There is nothing quite like unearthing a gem with the help of a "local." In doing a review of my Chicago restaurant files, discovered that Toscano's is closed. It breaks my heart!

                  1. I'm sure I must have been there sometime in the 40's or 50's, but the place I remember is La Fontinella. Your description of Toscano's brought memories of that place. I just checked Citysearch, and it is still there!

                      1. I had to reply to you. I was just asking people at work if anyone had ever heard of Toscano's!
                        I didn't remember the address but, certainly remember going there with my family in the 60's. Cheese ravioli for me. And, of course, the fruit from my Aunt Rose's rum stone sour ; )

                          1. My mother loved Toscano's, and so did my step-dad, and I was a lucky kid - in my teens- to be invited along to regular visits to Toscano's in the mid-1960s. What a great food street Oakley was, back then. A great enclave of S. Side Italians, also.

                              1. re: gomexico

                                You can still get a feel for the neighborhood at Bruna's. Altho I haven't been in several years, my understanding is that it's as good as it's always been (well, almost, anyway). By the way my favorite in the area (and a highpoint IMO of Italian-American style dining)was always Febo's ("Famous for nothing.")

                                  1. re: jbw

                                    Febo's - the corner location on Western Ave. What a crowd the restaurant would draw . . . when there were many businesses (including factories) in the neiighborhood. My Mom was partial to Toscano's and though she'd go to Febo's I wasn't tagging along. ;-( It's a "Mexican neighborhood" now and though I've been back I don't like what's there - when it comes to Italian. Nothing to brag about, when it comes to Mexican food, either - unless I've missed mention of it.

                                  2. I remember Toscano's VERY well. I used to live on 25th & Western, across the alley from Febo's (remember that place?). One of my first jobs was waitressing at Toscano's in 1970. I loved Toscano's & am so sorry to hear that it's closed.

                                      1. I remember Toscano's very well. I spent a lot of time at Febo and Toscano's. Those restaurants were great neighborhood restaurants. In the summer when you walked down the street on a warm summer's night after eating at one of those venerable restaurants, you would see people siting out on front stoop, and you would stop and have a brief conversation. Unfortunately, these days are long gone, but we have the wonderful memories.

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