You finally get a babysitter and both manage to leave work at a reasonable hour. Maybe it’s your anniversary, or maybe you just realized you haven’t been able to enjoy your company together in more than three weeks. Either way, you need a restaurant where you can have a memorable night out to rekindle some love.
Hi, we’re the Ben Lalez Team, and between showing properties and living here ourselves, we’ve eaten our way through most of Chicago’s date-night spots. Some are exceptional, while others make you wish you’d just ordered pizza and stayed at home.
In this article, we’re going to introduce 13 spots in the city where you and your significant other can have a great date night!
Tre Dita
Tre Dita is inside the St. Regis Hotel, so you already know it’s going to be expensive and fancy. They have their own pasta lab, which means you absolutely have to try the pici cacio e pepe or duck ragu pappardelle. Fair warning… both are rich enough that you might stop talking entirely and just focus on eating.
The dining room has art deco details and views of the river (perfect place to make a proposal if you’re looking for a venue). Everything feels fancy here, which is good if that’s what you’re going for.
The steaks are dry-aged and made for sharing, assuming you and your date don’t get competitive about food.
Location: https://maps.app.goo.gl/T84tPuTtTQxZk6wf6
Cuisine: Tuscan steakhouse with house-made pasta.
What to expect: The setting and the food live up to the hype. Suitable for anniversaries or when you want the night to feel special.
Price: $$$$
Reservations: Tables drop at midnight a week out on OpenTable. They go fast, so if you miss out, the Bar Tre Dita next door does walk-ins and has a smaller menu.
North Pond
You have to walk through Lincoln Park to get here, and the restaurant can be found in an old Arts and Crafts cottage right by the pond. You’ll find windows looking out over the water, and you can see the skyline in the distance.
Chef César Murillo runs a seasonal menu where everything’s farm-to-table and changes based on what’s available. We think it’s one of the better spots in the city if you want something that feels intimate and away from the city noise.
Location: https://maps.app.goo.gl/QprSRe8fVppc2H936
Cuisine: Seasonal American, prix-fixe.
What to expect: You’re eating next to a pond in the middle of a park. What else can we say?
Price: $$$$
Reservations: Book a few weeks ahead for weekends, and expect business casual dress code.
Bavette’s Bar & Boeuf
Bavette’s has a 1920s speakeasy vibe to it with red leather booths, candles on every table, jazz in the background, and servers in waistcoats.
The bone-in ribeye is one of the best steaks in Chicago. Splitting a big piece of meat by candlelight is about as classic as date night gets. They also have seafood towers and sides, plus a massive slice of lemon meringue pie if you make it to dessert.
Location: https://maps.app.goo.gl/KsCtXHqPogkFGmKE7
Cuisine: Classic steakhouse with French touches.
What to expect: Dark, intimate, and romantic.
Price: $$$$
Reservations: They’re tough to get, although walk-ins are possible if you show up right at 4pm on weekdays or 3pm on weekends. Spots get released 21 days out on Resy and book up fast.
Geja’s Cafe
Geja’s opened in 1965 and has been doing fondue ever since. The whole place is underground, lit mostly by candles, with curtained booths that give you real privacy. A flamenco guitarist plays live music while you eat.
Dinner here is cheese fondue first, then you cook meat and seafood in hot oil at your table, then chocolate fondue for dessert. It takes a while, so we think you’ll enjoy a nice, relaxed night out here.
Location: https://maps.app.goo.gl/KfBiVx9877od4r6d7
Cuisine: Swiss fondue, multi-course.
What to expect: Candles, privacy curtains, and feeding each other fondue!
Price: $$$
Reservations: You’ll want one, especially on weekends. Valentine’s Day is basically impossible.
Boka
Boka has held a Michelin star for over ten years. Chef Lee Wolen runs a seasonal menu that you can do à la carte or as an eight-course tasting for $195.
The dining room has soft lighting with booths and a greenery wall with some pretty interesting animal portraits. The food here is outstanding. The duck and scallops are stellar, though the menu changes with the seasons.
We recommend this if you want something upscale but not uncomfortable. It’s fancy enough to feel like an occasion, but relaxed enough that you won’t feel like you don’t belong.
Location: https://maps.app.goo.gl/mxbWbVjbSPLuHqYaA
Cuisine: Contemporary American, fine dining.
What to expect: Good food, nice atmosphere, not pretentious.
Price: $$$$
Reservations: Book a few weeks out if you’re looking for a weekend spot.
Maple & Ash
Maple & Ash is loud and dramatic, with big curtains and lots of candles. We think it’s a pretty cool vibe.
They have a $200 per person tasting menu called “I Don’t Give A F@K” where the kitchen sends you whatever they want. No substitutions, no questions. If you’re celebrating something, mention it when you book, and they’ll print a custom message on your menu, usually with profanity.
This isn’t the place for a quiet, intimate dinner. It’s for couples who like energy and don’t mind spending money to have a good time.
Location: https://maps.app.goo.gl/qzRNx2aPDzsfRnLz8
Cuisine: Modern American steakhouse.
What to expect: High energy, theatrical, and fun.
Price: $$$$
Reservations: Book a couple of weeks ahead, and make sure to tell them if you’re celebrating something.
Virtue
Virtue does Southern cooking like nobody else. Chef Erick Williams runs the kitchen, and you’ll want to come here if you like buttermilk biscuits, short ribs with collard greens.
The dining room has wood details and warm lighting, and the service is friendly. The skillet cornbread is a must, and if you make it to dessert, get the banana pudding.
Location: https://maps.app.goo.gl/vXU6JYEKCsaR3fwA8
Cuisine: Southern American, elevated.
What to expect: Great food, relaxed atmosphere, genuinely warm service.
Price: $$$
Reservations: Book a week or two ahead. The restaurant has won James Beard awards, so it stays fairly busy.
BLVD Steakhouse
BLVD is designed to look like a 1950s Hollywood supper club. It has big chandeliers, posh seating, and a 20-seat bar in an atrium. There are multiple dining rooms, and you might feel like you’re somewhere on the Sunset Strip.
The menu is standard high-end steakhouse – filet, tomahawk ribeyes for two, oysters, with good martinis. Everything’s done well. It’s the kind of place where you dress up a little and make an evening out of it.
You’re in Fulton Market after dinner, so there are plenty of bars nearby if you want to keep the night going.
Location: https://maps.app.goo.gl/aVZSQqBAaU13rwrA8
Cuisine: American steakhouse.
What to expect: Old Hollywood glamour, solid food, and fancy feelings.
Price: $$$$
Reservations: Book ahead for weekends, especially if you want a specific booth.
Piccolo Sogno
Piccolo Sogno means “little dream” in Italian. The outdoor patio is covered in string lights and greenery, set up in a courtyard away from the street. In summer, it’s one of the best spots in the city for eating outside.
The indoor dining room is nice too, with rustic Italian decor. Chef Tony Priolo’s menu is very Italian. Handmade pastas, wood-fired pizzas, whole fish, and an all-Italian wine list.
We think you’ll like this if you want something that feels romantic without being too fancy. If you’re a patio person, you’ll want to eat here.
Location: https://maps.app.goo.gl/sUQRtEL13iRg6EaY7
Cuisine: Traditional Italian.
What to expect: The patio is hard to beat in summer.
Price: $$$
Reservations: Patio books up weeks ahead in summer. Specify outdoor when you reserve.
Ciccio Mio
Ciccio Mio is behind an unmarked door in River North, and it’s tiny. There is limited seating, and they have vintage art and chandeliers everywhere. Candles provide most of the light.
The menu is Italian-American comfort food. Chicken parmesan, bruschetta, and pastas. The space is so small that it automatically feels intimate. You’re sitting close, talking quietly, and the old-mansion decor makes it feel like you’re somewhere secret.
Location: https://maps.app.goo.gl/PT8bnMNmUmMFethc8
Cuisine: Italian-American, red sauce classics.
What to expect: Tiny, cozy, feels exclusive just because of the size.
Price: $$$
Reservations: Hard to get. They release bookings 21 days out at 9am. Walk-ins are possible but not reliable.
Gibsons Italia
Gibsons Italia is right next to the Chicago River, so almost every table has a view of the water and downtown. The restaurant is modern and polished, usually packed with a mix of locals and people visiting the city.
The menu combines steakhouse standards with Italian dishes. You can expect prime steaks, fresh pastas, risotto, and a big wine list. The spaghetti cacio e pepe gets finished tableside in a wheel of pecorino, which is a nice touch.
Location: https://maps.app.goo.gl/XWpTpCjUhdADbzq69
Cuisine: Italian-American steakhouse.
What to expect: River views, solid food, and great wine.
Price: $$$$
Reservations: Book at least a week out. Ask for a riverside table when you reserve.
Armitage Alehouse
Armitage Alehouse is designed to look like a Victorian London pub with its fireplace, vintage art, taxidermy, and burgundy leather booths.
The menu features British pub food with Indian cuisine. Pot pies and fish and chips next to tandoori chicken, samosas, and curries. The drink list has craft beers, classic cocktails, and old wines.
We recommend this if you want something different. The atmosphere is unique and cozy.
Location: https://maps.app.goo.gl/mFX9NwyCxt3SgxMv5
Cuisine: British gastropub with Indian influences.
What to expect: Cozy with a unique atmosphere.
Price: $$$
Reservations: Very tough. Ten tables online, released 14 days ahead at 9am on Resy, and they’re typically gone in minutes. Walk-ins can work if you show up early, between 4-5pm. The summer patio is first-come, first-served.
Alinea
Alinea is less of a restaurant and more of an event. Three Michelin stars, 15-20 courses, and things you’ve never tried before and probably won’t try again. Some dishes levitate. Others come on pillows of scented air. Dessert might get painted on your table. Trust us, you’ll be taking a lot of photos for the ‘gram.
You’ll spend the whole meal surprised by what shows up next. It’s expensive, hard to book, and nothing like a normal dinner.
Just a note… this isn’t for everyone. If you want candlelight and quiet conversation, go somewhere else. But if you and your date like trying new things and want a meal you’ll talk about for years, this is it.
Location: https://maps.app.goo.gl/1cmpKSpcJvRfc7Sd9
Cuisine: Molecular gastronomy, progressive American.
What to expect: Shared surprise. You’re both figuring it out together.
Price: $$$$
Reservations: Required. Ticketing system, releases in blocks two months out. Plan ahead, dress well. Clean your phone camera lens.
Final Thoughts
As you can see, you have plenty of choices depending on your mood. What we love about Chicago is that it has enough date-night restaurants to cover every type of couple. Nothing is ever boring. And if you want to be really adventurous, try one of them every 30 days, and check back in with us in 13 months!
That’s it for us! Yes, we sell real estate, but we also spend a lot of time thinking about neighborhoods and what makes them work for different people. Restaurants are part of that. If you’re trying to figure out which Chicago neighborhood fits your life, give us a shout, and we’ll be happy to share our restaurant stories with you!
