13 top restaurants for every kind of date in Chicago

Machine’s charming first-date perks include an onsite floral service. | Credit: Machine
A fresh flower bouquet attached to one of the seats at Machine in Chicago

Whether you’re looking for a full-on spectacle or a cozy and casual night out, Chicago’s most romantic restaurants have it all. A first-date favorite sweetens the deal with tableside flower carts. Pitchers of hibiscus sangria keep the good times flowing at a Mexican hotspot made for group dates. And if you’re looking to propose, you can’t beat a lavish steakhouse known for the best Chicago River views. 

This guide pairs Chicago restaurants with romantic occasions from first dates all the way to milestone anniversaries. These are Chicago’s 13 best date-night restaurants.

For a first date

Machine: Engineered Dining and Drink  (Bucktown/Wicker Park)

Large red floral arrangements, brassy accents, and a bar lined with heavy, Persian-inspired fabric at Machine in Chicago
The sultry, floral interiors at Machine in Wicker Park make it a first-date favorite. | Credit: Machine: Engineered Dining and Drink

This Wicker Park restaurant is all about flower power: Machine features an onsite floral service to complement its modern American menu and sultry interiors. Impress your date with a pre-made arrangement, or take things up a notch and build your own bouquet from the tableside cart. If you’re drinking, consider one of the very Instagrammable cocktails like the gin-forward Caged & Infused, which comes with a tiny hammer for smashing its spun-sugar shell—can you say ultimate icebreaker? 

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Big Star (West Town, Wicker Park)

Several Mexican dishes on a table at Big Star in Chicago, including white shrimp with chipotle-mezcal salsa and yellowfin tuna tostadas
Image caption: Both Big Star locations specialize in bold Mexican dishes like white shrimp with chipotle-mezcal salsa and yellowfin tuna tostadas. | Credit: Kelly Sandos

Head to this crowd-pleaser for a stress-free first date. The tacos, seafood, and cocktails at both locations come with a side of easygoing charm. Get to know each other over Oaxacan old fashioneds, chips, and guac. If drinks turn into dinner, you’ll feast on housemade corn tortillas stuffed with beer-battered tilapia, carnitas, or carne asada. Then stretch your night even further at the bar, stacked with bottles of mezcal and tequila.

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Book Big Star Wicker Park

 

For a second date

Peanut Park Trattoria (Little Italy/University Village)

This neighborhood gem comes from the team behind other inviting local faves like Coalfire Pizza and Tempesta Market, so its warm and rustic vibe is very much on brand. Get better acquainted over linguine vongole, perfectly blistered pizzas, and tender fresh octopus—the restaurant’s tiny but mighty menu earned a nod from The Chicago Tribune’s dining critic just a few months after it opened in 2021. In other words, Peanut Park has second—and third and fourth—date written all over it. 

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For an anniversary/romantic milestone

Maple & Ash (Gold Coast/Streeterville)

This multi-story steakhouse doesn’t hold back on high-roller touches, making it the perfect setting for a splashy occasion: Caviar comes in three varieties, Krug Grand Cuvée is available by the glass, and the menu includes a trio of specially sourced Japanese wagyu. Plush velvet chairs and candelabras add to the sexy vibes at this special-occasion superstar.

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Sepia (West Loop)

Sepia has gracefully walked the line between special-occasion restaurant and neighborhood gem since opening in 2007, even landing a MICHELIN star in the process. Its stylish interiors bring out the chandelier-lined space’s past life as a 19th-century print shop—without being precious. The same goes for chef Andrew Zimmerman’s stunning but unfussy four-course menu, which features winners like sea urchin chawanmushi and grilled pork collar, sure to bring some magic to your milestone. 

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Alla Vita (West Loop)

Acclaimed chef Lee Wolen serves a menu that can be dressed up or down at this Italian masterpiece, depending on your celebration mood. If you’re looking to splurge, go for the tuna crudo and wood-fired sea bream. If you’re keeping it casual, get pizza and housemade pasta. Scoring a table at Alla Vita can be trickier than getting a burger at Au Cheval, but you and your date can always grab a spot at the bar. Plan ahead to sit in the dining room, with its fabric-covered ceiling and wooden archways.

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For a proposal-worthy place 

Kumiko (West Loop)

The latticed, Japan-inspired bar Kumiko in Chicago
The latticed bar at Kumiko is just one of the many cues the spot takes from Japan. | Credit: Sammy Faze

Julia Momosé’s Japanese-inspired cocktail bar is detail-obsessed, from the hand-carved ice to the delicate glassware. And what it lacks in space, it makes up for in style: Kumiko’s elegant accents, like geometric patterns in the wood partitions and brass screens that each have their own hidden meaning, make it an extra-meaningful spot to pop the question. Celebrate with Momosé’s next-level cocktails, and don’t close the deal without the bar’s truffled milk toast and honey ice cream. 

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Gibsons Italia (West Loop)

Gibsons Italia may get a ton of attention for lavish food like gold-extruded pasta and massive platters of Alaskan king crab. But what makes it proposal worthy are its views. Overlooking the Chicago River and flanked by skyscrapers, this contemporary, Italian-accented steakhouse is a stunning setting for a blockbuster dinner. The spacious dining room features plenty of white tablecloths for a romantic evening. The only thing that could rival this view? A diamond.

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For a group date

Tzuco (River North)

A spread of modern Mexican food at Tzuco in Chicago including guajillo-roasted octopus, carne asada with roasted fingerling potatoes, P.E.I. mussels with saffron beurre blanc and dried chorizo, and more
Chef Carlos Gaytán’s modern, group-friendly menu at Tzuco includes guajillo-roasted octopus, carne asada with roasted fingerling potatoes, and more. | Credit: Tzuco

Each dish has a personal story to tell at this Mexican hotspot. But Tzuco doesn’t take itself too seriously, which means it’s ideal for a chill get-together with friends. Take in the earthy interiors—chef and owner Carlos Gaytán lined the space with objects that remind him of his hometown of Huitzuco, Mexico—and order a pitcher of hibiscus flower sangria for the table before digging into killer signature dishes like guajillo-roasted octopus and cochinita pibil.

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Bar Mar (River North)

José Andrés’s elegant seafood spot is the perfect group date destination, thanks to an impressive tapas lineup and awe-inspiring interiors, including a glowing octopus sculpture. Ideally, all meals should start with oysters, but especially when dining at Bar Mar, where they come with black pepper and fruit vinegar. Follow it up with something sexy, like ceviche with leche de tigre or playful hamachi cones. Either way, you’re in for a special meal that channels peak coastal vacay vibes.

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For an adventurous, transportive date

Holu (Chinatown) 

Chicago has lots of meat-heavy spots, but this elegant Chinatown restaurant rises above the rest. Holu is all about Japanese- and Korean-inspired tabletop cooking. Luxe cuts of meat are offered by the ounce, so you and your date can mix and match A5 Japanese wagyu with prime black Angus; servers who navigate the smokeless grills like pros add to the one-of-a-kind experience. But it’s not all beef: Holu’s global menu also includes specials like Iberico ham and jumbo Australian lobster.

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For an intimate and cozy night out 

Rose Mary (West Loop)

Plants in various baskets hang from the ceiling at Rose Mary in Chicago.
Find an intimate corner under the hanging plants at Top Chef winner Joe Flamm’s passion project, Rose Mary. | Credit: Kinship

You’ll find lots of cozy corners for cuddling at this restaurant by Top Chef winner Joe Flamm, from the chef’s counter to under the hanging plants by the wood bar. Flamm’s Midwest-meets-Mediterranean restaurant is a love letter to Adriatic soul food, like burek, a flaky pastry filled with cheese and other seasonal ingredients, plus gnocchi with slow-cooked Croatian beef stew—and it’s these hearty but unique flavors that lead couples to plan repeat visits to this rustic-chic charmer.

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For an evening of eatertainment

The Lakefront Restaurant (Lincoln Park)

It’s not just a postcard-perfect Lake Michigan view that draws couples to this upscale tavern. The Lakefront is also popular for its neighboring theater, known for candlelight concerts and stand-up comedy acts. Fuel up before or after the show with seasonal Midwestern hits like hanger steak and frites or a gruyère-topped brisket dip sandwich. Bonus points for the locally leaning beer menu.

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Tried them all? Check out other options here.

Lisa Shames is a writer focused on travel and food culture in Chicago and the US contributor for Sogoodmag. Find her on Instagram.  

Sarah Freeman contributed to this guide.

Find your table for any occasion