Best places to eat and drink in Chicago Little Italy

With Taylor Street between Ashland and Morgan as its epicenter, Chicago’s Little Italy has undergone major changes over the last several years. What hasn’t changed, though, is it’s where my and my family’s roots are. We have our ideas on the best restaurants in Chicago Little Italy, as well as our favorite drinking establishments, and they range from mainstays that have been around for decades to new(er) kids on the block. Because I lived there for most of my life, I’m often asked about the best places to eat and drink in Little Italy. Here are my picks:

Pompei Little ItalyBest for a casual, sit-down meal: Pompei Little Italy. This is a Taylor Street institution that originated more than 100 years ago. Today, it is an enormous cafeteria-style, Italian-American eatery and my go-to for comfort food. The menu has expanded well beyond the original pizza and bread to include items such as fried calamari, eight-finger cavatelli, and pepper and egg sandwiches (the best in the city, as far as I’m concerned). Pompei is an excellent place to have a family meal in a relaxed environment and not have to break the bank.

Best spot to watch the game: Vintage Lounge. As the name would imply, Vintage Lounge aims to recall an earlier time. The mahogany decor, exposed-brick walls, and wrought iron accents throughout the expansive space are reminiscent of and inspired by the 1920s. There is nothing old-fashioned about the food, drinks, and entertainment, though. Vintage offers a full restaurant menu, as well as half-off bar food items; an array of beers and top-shelf liquor; specialty cocktails; and frequent drink specials. With seven televisions and four projection screens inside the bar, and three televisions out in the beer garden, “the game” is sure to be on, whether you stop in on a Sunday Funday or a on different day of the week. Vintage Lounge also is an excellent option for fans heading to Chicago Blackhawks or Chicago Bulls games due to its close proximity to United Center.

Vintage Lounge

Best sweet treats: Scafuri Bakery. Originally opened in 1904 by Italian immigrant Luigi Scafuri as a tribute to his native culture, the bakery was kept open by family members for the next 100 years. In 2007, Luigi’s daughter, Annette Mategrano, at age 90, decided to close up shop. Thankfully, Annette’s great-niece, Michelle, decided to continue the family tradition and began work to renovate and re-establish Scafuri Bakery, and it reopened in May of 2013. Michelle and her team have maintained the same quality of products using the same century-old family recipes while incorporating modern offerings like free Wi-Fi and live jazz. As for the treats, choose from doughnuts and cookies to more traditional Italian goodies like sfogliatelle and cuccidati.

Scafuri Bakery

Best place to go without the kids: Three Aces. I make it no secret that Three Aces is my favorite place in the entire city of Chicago. Since it is in Little Italy, naturally I had to include it on this list! One thing I love most about this “rockabilly gastropub” is its tagline: “The Italian countryside meets the American farmhouse… in Keith Richards’ basement bar.” The description is fitting and it’s the main reason I suggest leaving the kids at home. Mom and Dad need the chance to fully enjoy the outstanding beer and liquor selection at Three Aces, consisting mainly of American craft beers and spirits. While the setting definitely leans more toward the bar atmosphere, it’s the food at Three Aces that steals the show. The farm-to-table menu is divided into four main sections (Farm, Mill, Sea, and Barn), features local ingredients, and changes seasonally. The menu also includes year-round staples like pizzette (personal pizzas) and bolognese fries (one of my favorite dishes). Also, the outdoor patio at Three Aces is one of the best in the city.

Three Aces ChicagoCan’t pick just one place to try? Fear not! Come to Chicago Festa Italiana, the annual celebration of Little Italy’s history and heritage. The street festival runs August 14-17, 2014. Along with the establishments I’ve chosen here as my favorites (as well as many others from the neighborhood), there will be activities like grape stomping and a meatball-eating contest; live music on three stages; and carnival rides for the kids. Come back to the old neighborhood!

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17 Responses to Best places to eat and drink in Chicago Little Italy

  1. Amber DeGrace July 28, 2014 at 7:42 am #

    Three Aces sounds great! Actually, they all do. If I ever find myself in Chicago, I’m definitely referring to this list. 🙂
    Amber DeGrace recently posted…The Ultimate Summer Roadtrip PlaylistMy Profile

  2. Anne July 28, 2014 at 11:00 am #

    If there’s one thing I’d count on you to know it’s 1) Chicago and 2) Italian food. So I LOVE this. Thanks for sharing! I need to get back to Chicago now, please!
    Anne recently posted…Venice in Black and WhiteMy Profile

  3. Jenny | A Thing For Wor(l)ds July 28, 2014 at 11:12 am #

    Huge mistake reading this post before breakfast. You should have included a warning up top.
    I remember you raving about Three Aces at Bloghouse! I love the whole idea of “Farm to Table,” and also bolognese fries??? Just……need.
    Jenny | A Thing For Wor(l)ds recently posted…Bathroom Linguistics: How Stall Graffiti Can Help You Learn a LanguageMy Profile

  4. Cathy Sweeney July 28, 2014 at 11:30 am #

    Who better to get Little Italy restaurant tips from than you?! Can’t wait to try these place out sometime. they sound wonderful It’s been ages since I was in that area. I also can’t believe that I’ve never been to Festa Italiana in Chicago — a shame!
    Cathy Sweeney recently posted…Discovering Nova Scotia Wine and FoodMy Profile

  5. Mindi July 28, 2014 at 7:42 pm #

    We totally must go to Three Aces on our next Chicago trip. Those bolognese fries sound off the hook!
    Mindi recently posted…Las Vegas Restaurants – 5 RecommendationsMy Profile

  6. Kristin July 28, 2014 at 7:58 pm #

    I love exploring other cities’ Little Italy! In NYC ours has been overtaken by Chinatown so it’s not really the best place to go anymore. Love your pics and fun categories!
    Kristin recently posted…The Golden Nugget Flea Market– Great Finds and a Short Drive from NYCMy Profile

  7. Amber July 28, 2014 at 10:28 pm #

    Wish I had this list when I lived in Chicago, but I am sure the area has changed so much since I lived there!
    Amber recently posted…Seeing Chicago From the River – Chicago Electric BoatsMy Profile

  8. Aggy July 29, 2014 at 6:50 am #

    Wow you sure have a great list of places! I like the sound of Vintage Lounge, I don’t know when I can come to Chicago, but I’m sure saving this!
    Aggy recently posted…Semarang in PicturesMy Profile

  9. Lucy July 29, 2014 at 12:15 pm #

    Not a good post to be reading just before dinner! They all sound great – though I especially like the sound of the 1920 style cocktails.
    Lucy recently posted…My third year On the LuceMy Profile

  10. Nick (Nick's Travel Bug) July 29, 2014 at 8:39 pm #

    Vintage Lounge sounds cool because of the 1920s-era decor. I’m sure they make some unique cocktails as well. I’ll definitely have to check out Little Italy next time I’m in Chicago.
    Nick (Nick’s Travel Bug) recently posted…FotoFriday: Hot Air Ballooning in PortlandMy Profile

  11. Erin - The World Wanderer July 30, 2014 at 8:42 pm #

    When I come to visit you, we are going to go to alllll of these! So yummy!
    Erin – The World Wanderer recently posted…The Streets of Lecce, Italy.My Profile

  12. Raul (@ilivetotravel) July 30, 2014 at 9:00 pm #

    Chicago is such an awesome city. I love going over and over and discovering new places. I consider this post an invitation to go back and try restaurants like this one!!
    Raul (@ilivetotravel) recently posted…Iceland, Where Is Brooke Shields??My Profile

  13. the lazy travelers July 31, 2014 at 9:01 am #

    can’t believe that neither of us have every been to chicago. when we DO come (and we will), we’re hitting up three aces fo sho. wanna come?
    the lazy travelers recently posted…city dwellers: philadelphia’s center cityMy Profile

  14. Traveling Ted July 31, 2014 at 7:22 pm #

    Great tips for Chicago. I have not experienced this neighborhood as it is kind of far, but it looks worth the visit based on this post.
    Traveling Ted recently posted…A White River State Park Segway Tour oddityMy Profile

  15. Chanel | Cultural Xplorer August 1, 2014 at 2:41 am #

    Gahh! I wish I had this list to refer to after BH! So many great places to try….. looks like I will have to make a trip back soon…
    Chanel | Cultural Xplorer recently posted…Meet The Blogger: Jenny from A Thing for Wor(l)dsMy Profile

  16. Lance | Trips By Lance August 1, 2014 at 10:46 am #

    I’m not sure if my next trip to Chicago will provide enough time to stop off here (we’re heading up to Traverse City from Chicago) but I am filing this away. We make it to Chicago from time to time. Three Aces sounds like the type of restaurant my wife and I would enjoy.
    Lance | Trips By Lance recently posted…Puerto Rico Run: Condado to Old San JuanMy Profile

  17. Pola (Jetting Around) August 1, 2014 at 7:01 pm #

    Francesca, grazie mille for this!! I haven’t explored your old ‘hood enough, mostly because it just… doesn’t seem to have enough stuff, like Little Italy in e.g. NYC or Boston, at least that’s been my impression. Now I know where to start and it will be Scafuri. Sweets, WiFi, and LIVE JAZZ? You know it’s a place for me!
    Pola (Jetting Around) recently posted…Tasting Slovenian cuisine with SlocallyMy Profile

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