Apart from a dual gluten and grape allergy, there’s really no reason not to eat pasta and drink wine by yourself every now and then. It’s one of life’s great combinations, one that you don’t need to come up with an excuse to do. But when choosing a spot, there are a couple of non-negotiables: a relaxed atmosphere, nice bar seating, high-quality pasta, and wine by the glass. When you’re looking for the best kind of me time, stick to the spots on this guide.
Two conflicting ideas can exist at the same time: you might want to be left alone, but also be surrounded by people having a good time. And a solo meal at the bar at Alla Vita in the West Loop is the best way to steal some vicarious socialization. It’s incredibly popular, and always buzzing with everyone from couples and small groups, to people eating at the bar and the staff serving them. And the impressive space—decorated with hanging plants and a very cool fabric wave ceiling— roughly the size of Terminal 2 at O’Hare but with way better food. Particularly the cacio e pepe ricotta dumplings. They can only be described as “sexy”, as they’re firm on the outside, have a creamy ricotta center, and swim in a silky cheese and black pepper sauce. Resist the urge to light up a cigarette after eating.
If you don’t know about this little Italian restaurant in Logan Square that quietly opened in 2020, now you do. The space is small and dimly lit, busy without being chaotic, and has a not-crowded bar that’s perfect for a bowl of pasta and glass of wine. The menu is short—just some hot and cold small plates and a few entrees among other things. It’s all good, but you’re here for the pastas, like cacio e pepe and mezze maniche. They’re wonderfully chewy, and available in half portions in case you decide to order more than one. You should.
This Italian restaurant in Humboldt Park has the laid-back feel of a European cafe, filled with people laughing while pretending to be on vacation. Plus, Segnatore has friendly bartenders, and a long wooden bar that takes up almost half the restaurant. All of that makes this spot perfect for a solo meal to begin with, but the main reason we love coming here is because of the excellent pasta. Each one has a creative twist that makes things exciting. Their “lasagna” is deconstructed into a pile of handmade garlic mafaldine, whipped ricotta, and rich mushroom bolognese that rivals any meat version. Delicate capellini is tossed with a black kale pesto, blue cheese, and walnuts—which sounds like a lot of bold ingredients at play but unlike your ex, it’s strong enough to hold up to the pressure. This place is begging to become your new forwarding address.
OK, so Tortello doesn’t have a _bar_ bar. But this brightly lit, counter-service restaurant in Wicker Park does have plenty of space perfect for just one person, and several wines available by the glass, so it counts. This place specializes in delicious handmade pasta, and you can get things like burrata-filled tortellini, cacio e pepe, or squid ink bucatini. Whichever pasta you choose, make sure to order some of their focaccia with ricotta and honey to go with it. Also worth noting: They have a cute sidewalk patio if you want to eat your pasta outside.
After an eight-hour day filled with unproductive meetings and a desk salad for lunch, at 5pm you just need a glass of wine, some food, and to be left alone. Head to Joe’s, an easy-to-get-into wine bar in the West Loop. The pasta section of the menu is pretty limited, but the special of the day is good enough to make you forget about the morning’s brutal conference calls with corporate HQ.
Enoteca Roma is a small, quiet spot in Wicker Park, and it’s the kind of neighborhood Italian restaurant you imagine New Yorkers taking for granted every day. Sit at the bar with the penne arrabiata or the campanelle topped with venison bolognese, along with a big glass of red. A lot of the pastas come in half orders, which is great if you don’t want leftovers. Just don’t ask for a half order of Chianti.
We’ve long been huge fans of Riccardo Trattoria, a somewhat upscale Italian restaurant in Lincoln Park. But right across the street is Riccardo Enoteca, a more casual place from the same owners. Both are excellent choices, though Enoteca is easier to get into and has a full bar where you can sit and order the essentials.
The idea of “Midwestern pasta” might conjure up a nightmare of noodles, crescent rolls, and cream cheese in a casserole pan. But thankfully, that’s not what’s happening at Daisies in Logan Square. This Midwest-focused restaurant uses seasonal ingredients to make dishes like beet agnolotti topped with creme fraiche and salmon roe, and tajarin topped with cracklins. It’s not pasta as we usually think of it, but the local wines and produce make it a great option for your solo dining.
The only downside to Monteverde in the West Loop is that it’s hard to get any reservation that won’t lead to “early bird special” jokes. But when you’re a party of one, it’s easy to grab a seat at the bar right away. Order any (or all) of the fantastic handmade pastas, particularly the cacio e pepe or the fusilli with ragu. This sauce normally only comes with the ragu alla Napoletana, but they offer it by the bowl if you ask, which you absolutely should. Plus, when you sit at the bar you have a view of the kitchen, and you can sip your wine and pretend that someday you’ll try making handmade gnocchi even half as good.
Did you just find a boot on your car and currently need a place to knock back a little too much house wine and go face-first into a pile of spaghetti and meatballs? Pasta Palazzo in Lincoln Park has you covered. The environment is casual and the food is simple and inexpensive - most pastas cost around $10, and adding a protein won’t be more than a few extra bucks. So after calculating exactly how much you owe in parking tickets, this should be your next move.
If Pasta Palazzo is where to go in your sweatpants, RPM Italian is the complete opposite. There’s nothing low-key about this spot in River North, but there’s a certain amount of anonymity that’s relaxing when you’re dining solo at the bar of a sceney restaurant. The people-watching here is excellent, and so are the handmade pastas - the bucatini and cavatelli are some of our favorites in the city. Plus, the infuriatingly-small-when-sharing portions are perfect for one person.
Head to Bar Roma in Andersonville to hang out in a rustic space that has a lot of wood and distressed furniture. This place even has artfully placed bags of flour lying around, just to remind you that they make all their own pastas. It’s the kind of enjoyable spot where, even if you had every intention of leaving after just one glass and a plate of cacio e pepe, you end up staying the whole night. We’re sure your dog will be fine.
Open since the early ’90s, Club Lucky is meant to resemble a 1940s Italian supper club, which means you can come here and channel strapping young Brando or, you know, the ’90s version. And while the main dining room is large and full of groups, the front bar area is where you want to be to have the fantastic handmade cavatelli in vodka sauce. You can definitely have a nice glass of wine here, but this place is also known for making great martinis. Proceed accordingly.
Bruna’s in the Heart of Italy is like stepping into a time machine. The atmosphere is almost aggressively old-school, which makes sense since it opened in 1933. As with most classic spots, you walk through the bar area to get to the back dining room, but we’re going to suggest you just don’t walk beyond the bar at all. The pastas, while not housemade, are well cooked and topped with rich, tasty sauces. Come here for the history, raise a glass to the end of Prohibition (also 1933), and try to find out if your bartender is a ghost.
River North isn’t brimming with understated restaurants. But you can easily stop in for housemade pasta and a glass of wine at Torchio, a solid neighborhood option for both of these things. The tagliatelle with bolognese is served in a parmesan basket, which you can wear as a hat if you want to make sure no one talks to you. Wave to the party trolleys as they roll by.
Just because a spot has a bar with regulars doesn’t make it “just like Cheers,” and obnoxiously saying so is usually wishful thinking. But Mart Antony’s might actually qualify. It’s on the border of West Town and the West Loop, and looks like a typical neighborhood corner tavern. It also happens to be a fantastic Italian restaurant. The owner, servers, and bartenders are all warm, welcoming, and will chat with you even if it’s your first time there. On any given night, it’s full of friends getting together after work and couples on casual dates—and you’ll quickly realize that this restaurant is their “place.” Sit at the bar, order the rigatoni diavolo or the gnocchi, and everyone at Mart Antony will know your name, eventually.
Bella Notte Ristorante
The Italian landscapes painted on the walls won’t trick you into thinking you’ve left Chicago, but that’s fine. A meal at Bella Notte in Bucktown will still take your mind off the vacation-destroying project you were just assigned, and so will a big glass of wine alongside the lobster fra diavolo. Enjoy the calm atmosphere and leisurely scroll through your phone looking at flights, just in case you decide to quit your job and take the vacation anyway.