Where I would make dinner reservations in Chicago

(Updated February 2019)

Let me first say that we don’t get out too much these days, but when we do decide to get out for a date night, we try to make it nice (who got that Housewife Dorinda reference?!). We get all dolled up, hit the town, and home by 9pm :). These restaurants below not only have incredible food, but the atmosphere make great date night spots or perfect of towners. So here are the places  I would make dinner reservations right now in Chicago.

chicago dinner reservations

Bavette’s Steakhouse- I really don’t have many “favorite” restaurants in Chicago, but this is one of them. Manny and I have been here many times and even celebrated my dad’s 50th birthday here with a large group. It’s really becoming one of the most popular steakhouses in Chicago. Their dry aged steaks are a MUST order along with their sides like spinach and elote style corn. It’s a dark, intimate place, but works for bigger groups too. Honestly, whatever you order, it will be good. It really lives up to all it’s hype and if you’re coming from out of town, you need to make reservations here very early in advance.

Monteverde– Holy pasta! If you are a pasta fan (I am not sure who isn’t?!), it’s absolutely amazing. Plus, it’s a head female chef, which is always a plus for me. Chef Sarah Grueneberg, former Iron Chef contestant, makes fresh pasta dishes like Cacio whey pepe or Gnocchetti with pesto that are mind blowing. We went for our 5 year anniversary and could only snag a 9:30pm reservation on a Friday night, but let me tell you, it’s worth waiting that late for a big meal. We started with crostinis like artichoke and octopus, shared pasta dishes (my favorite was the Cacia why pepe) and ended with the warm ganache tart. So, so so, good.

Our 5 year Wedding Anniversary at Monteverde


I’ve been here for brunch and dinner, and loved both. This Lettuce Entertain Restaurant takes you to Southern California with it’s airy vibes. Chef CJ Jacobson’s lighter dishes like spreads, dips, and Mediterranean small plates are incredible. Some standouts are the avocado and sweet pea hummus, chicken kefta and house made labneh (kind of like a yogurt-cheese). Both times I was there, the chef walks around and greets all the tables, it’s very welcoming. It’s good for a date or a girls night out. Either way, I love it and hopefully you will too.


This Chicago institution has been opened now for over 15 years now and I think it’s getting better with time. I like to call this “approachable fine dining”. Beautiful chandeliers, dark wood and detailed flooring, it’s old world meets new.  I celebrated my 30th birthday and even attended a rehearsal dinner. Chef Lee Wolen’s seasonal American food has won 7 consecutive Michelin Stars. The menu is constantly changing, but I did have short ribs and duck (I think both are still on the menu!). Service is incredible and there is an option for a tasting menu, which I would love to do next time. It’s just one of those classic places everyone should visit in their lifetime.

Siena Tavern

For a trendy night out, Siena Tavern is in the heart of River North. This is from Chef Fabio Viviani, former Top Chef contestant. He was actually named “one of the most talented Chefs in the world” by Forbes, so you can only imagine how good the food is. I had the pleasure of having a small, chefs dinner with him (you can read about it here) and he was a delight. He really made sure every plate was perfect and we were all satisfied with every dish. I would highly recommend the meatballs, watermelon and feta salad, gnocchi and the truffle mushroom pizza. It’s also a fun place to grab drinks and pizza at the bar and people watch. It gets very, very crowded on the weekends and I would definitely recommend reservations.

Piccolo Sogno

The name Piccolo Sogno literally translates into “little dream” and their food + patio really is like a dream. Sitting under the lights outside, you don’t’ have feel like you’re in Chicago. I met Chef Tony Priolo at Chicago Gourmet this past year and he is warm and inviting, just like the restaurant. He demo’d pumpkin ravioli that was INCREDIBLE!

He’s also a Chicago native, which I love. Now he has two other casual restaurants, Nonnina and Maillard Tavern, just in case you can’t get into Piccolo.

Every time I have been, I order either the ravioli or gnocchi, both are incredible. But one thing you must start with, the BURRATA. It’s amazing. Some of the best I’ve had in the city. The wine list is extensive, but the servers are super knowledgeable about what pairs well with your meal. Overall, amazing food and the patio is where it’s at.

Some places on my list next:

Pacific Standard Time, Aba, Etta, Gibson’s Italia, Giant and Mi Tocaya.

Chicago is filled with so many wonderful places, I could probably keep going. But these are just a few I’ve been over the years, some new and some that have been around for awhile. I hope you find some of these suggestions helpful. I’d love to hear any places you guys like to go on date nights. Add your comments below or DM me on Instagram.

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Until next time,