Dine with Me
- Chase
- Sep 29, 2024
- 3 min read
Updated: May 10

Imagine this: You’ve just concluded a successful day of meetings. Your colleagues might treat you to a dinner at one of the restaurants downtown, think Swift & Son's or RPM Seafood. But what about the nights that follow? What if I told you there are spots in this city where you can truly unwind, away from the bustle, in the company of someone who knows how to make an evening unforgettable?
The city holds a world of hidden treasures, far beyond the usual tourist traps. When work wraps up for the day, why retire to your hotel room or call it a night when there’s so much more to experience? As someone who knows this city like the back of her hand, I’m here to show you the Chicago that most rarely uncover, the side of the city that’s perfect for a night out with a charming woman who can match your wit and your tastes.
These aren’t just any places. I’m talking about the cozy, tucked-away lounges where the ambiance is just right for a gentleman to enjoy a good conversation with a woman who knows her way around art, finance, and, yes, even politics. Places where the atmosphere feels more like a private retreat than a public space, and where you never know who you might see or “not see” across the room.
A few of my favorite foods and cuisines are seafood - salmon, scallops, octopus, oysters, steak & wagyu beef, sushi, omakase, and tasting menus. Happen to know where to find the best of one of these? Let’s go!
I love fine dining, especially tasting-menus and Michelin star restaurants. Let's get to know each other over a fantastic meal. It’s one of my favorite ways to build connection and chemistry. I have a very sensual relationship to food and find delicious food, and even just reading through a menu, to be a powerful aphrodisiac. Here are my favorites I love to go back to again and again:
Sepia is a Michelin-starred restaurant with a sophisticated, vintage vibe, serving upscale American fare.
North Pond is nestled in Lincoln Park and offers a picturesque setting with elegant farm-to-table dishes.
Adalina is a sophisticated bistro spotlighting handmade pastas & strips.
Boka offers a blend of contemporary design and upscale seasonal dishes.
Miru or Tre Dita inside the St. Regis - views of Navy Pier, outdoor seating & a great selection of dishes.*
Alinea is known for its avant-garde cuisine and immersive dining experience.
Japanese food at Komo in west loop.
Nomi Kitchen - Inside the Park Hyatt, has an outdoor garden serves American cuisine rooted in French techniques.
Gibson's Italia offers Italian dishes and American steaks with a fireplace and a roof deck.
Brindille is a chic, Parisian-inspired restaurant offering refined French cuisine in an intimate, stylish space.
Momotaro for a multi-dimensional Japanese sushi experience in the west loop.*
Oriole is an intimate, 2-Michelin-star experience, blending creative flavors in a refined, modern setting.
Roka Akor is a modern take on Japanese food with a wood fired kitchen open to view in the middle of the restaurant.
Rooftop sushi at Nobu in the West loop.
And this list boasts restaurants I've yet to try:
Maple & Ash is a steakhouse in the Gold Coast with a menu crafted by two-Michelin-star Chef Danny Grant
Asador Bastian is a Chicago chophouse with Basque influences located in the iconic 1883 "Flair House"
Traditional Italian restaurant Alla Vita in the west loop.
Gino and Marty's is a narrative-driven Italian restaurant that tells a local prohibition story with a modern twist.
Fioretta blends steakhouse fare with elevated versions of old-world Italian cuisine.
Smyth + The Loyalist is a 2-Michelin-star spot offering farm-to-table dishes with a cozy, high-end vibe.
Kyoten serves upscale Japanese cuisine that explores the limits of taste, craftsmanship, and the human experience.
Omakase Yume is a chic, compact spot for high-end, multi-course Japanese menus.
Topolobampo is Rick Bayless's refined Mexican cuisine served in an elegant, art-filled space.
Mako is an elegant 2-Michelin-star sushi spot, offering an omakase experience that’s refined and precise.
Ever is a contemporary fine dining restaurant with impeccable design and 2-Michelin stars next to After lounge**
Elske is a 1-Michelin-star New American cuisine with Scandinavian influence in a minimal, stylish environment.
Kasama is Chicago's first Michelin Star Filipino eatery serving creative sweet and savory pastries.
Schwa showcases inventive New American fixed-price menus in a simple, homey space.
Moody Tongue's luxurious space focuses on beer-pairing with creative tasting menus.
Esme is an ever-evolving Michelin-starred fine-dining restaurant in Lincoln Park.
El Ideas offers an upscale, intimate dining experience serving American fare.
Atelier showcases a hyper-seasonal Folk Cuisine tasting menu.
Bazaar Meat by Chef Jose Andres is an industrial-chic steakhouse offering a menu of specialty steaks.