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?

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.

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.

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.

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.

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 & wooden archways.

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.

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.

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.

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.