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.
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.
So for those following along at home, we have Trattoria, Enoteca, and Osteria. Unlike its siblings, Riccardo Osteria in the West Loop has more of a sports bar feel, with a very long bar and an equally long menu filled with the same high-quality pasta you’ll find at the other Riccardos. Come here when you want to pair your food and drinks with athletes on screens making some kind of ball go back and forth. Or go to all three spots and then cast your vote for Riccardo Idol.
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.
Sono Wood Fired is a great utility player in Old Town with really good pasta, pizza, and bruschetta, and we always wonder why this place isn’t busier. But the good news is you can always find a seat at the small bar, and the service is consistently great. So when you’ve agreed to go support your friend’s amateur night at Second City, hit up this spot beforehand. And if you’re not good at fake laughing, consider a second glass of wine.
Italianette, one of the stalls in the Fulton Galley food hall in the West Loop, has excellent housemade pastas like cacio e pepe and saffron gemelli with a rich pork ragu. And while sitting in a fancy food court might not seem relaxing, this place manages to be. That could have something to do with their great happy hour, which has half-off glasses of wine from 5-7pm during the week. When your order comes, you’ll forget all about that unsettling “we need to talk” text you just got.
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.
Mart Anthony’s is an out-of-the-way spot on the border of West Town and the West Loop that looks like a typical neighborhood corner bar. Coming here lets you feel like you’re at the Italian version of Cheers in Mike Ditka–era Chicago, with warm and welcoming servers and bartenders who will chat with you even if you’re not a regular. Keep it simple and order the rigatoni with housemade sausage, or get the lasagna if you feel like eating enough food for every starter on the ’85 Bears. Whatever you get, expect to be covered in the leftovers department for about three days.
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.