The Ultimate Guide to Meeting Rich Men in Chicago
13 mins read

The Ultimate Guide to Meeting Rich Men in Chicago

Chicago, renowned for its vibrant culture, stunning architecture, and bustling economy, also boasts a thriving community of affluent individuals. From prosperous entrepreneurs to influential executives, the city is home to a diverse array of wealthy residents contributing to its dynamic social fabric. The allure of Chicago’s affluent population extends beyond mere financial status, encompassing sophistication, influence, and a zest for life.

We delve into meeting rich men in Chicago, offering insider tips and recommendations. Whether a resident or visitor, this guide is your gateway to the city’s upscale social scene. Meeting wealthy individuals demands insight, strategy, and a keen understanding of social dynamics.

Join us as we unveil the ultimate guide to meeting rich men in Chicago. From upscale lounges to high-end dining destinations, we’ll equip you with the knowledge to navigate the city’s affluent social landscape.

Best places to meet rich men in Chicago

1. Dating apps among rich men in Chicago

Dating apps are indeed popular among rich men in Chicago, offering them a convenient way to manage their social lives amidst their busy schedules. These platforms provide flexibility and access to a diverse pool of potential partners, aligning well with the lifestyles of affluent professionals.

Several dating apps cater specifically to wealthy individuals or those seeking affluent partners. Here are some dating apps that are prevalent among rich men in Chicago:

  1. MillionaireMatch
  2. AgeMatch
  3. SugarDaddyMeet
  4. WhatsYourPrice
  5. Seeking
  6. SecretBenefits
  7. SugarDaddy
  8. MillionaireLove

2. Chicago Athletic Association

The Chicago Athletic Association is located in downtown Chicago’s heart. It’s a testament to the city’s rich history and vibrant social scene. Meticulously restored, it’s now a luxurious hotel and social hub. The venue continues to attract the city’s discerning crowd. It was founded in 1890 as a private club for Chicago’s elite athletes.

Today, the Chicago Athletic Association Hotel preserves the grandeur of its storied past while offering modern amenities and world-class service. The hotel’s exquisite architecture, featuring stunning details such as ornate ceilings, marble staircases, and intricate woodwork, evokes a sense of timeless elegance.

One of the highlights of the Chicago Athletic Association is its diverse dining and drinking establishments, each offering a unique culinary experience. From the sophisticated ambiance of Cindy’s Rooftop, offering panoramic views of Millennium Park and Lake Michigan, to the cozy intimacy of the Cherry Circle Room, with its classic cocktails and refined cuisine, there’s something to suit every palate and occasion.

Beyond dining and drinking, the Chicago Athletic Association Hotel is a vibrant social hub, hosting various events and gatherings throughout the year. From art exhibitions and live music performances to wellness workshops and networking events, there’s always something happening to engage and inspire guests and locals alike.

3. The Aviary

The Aviary, nestled in Chicago’s trendy Fulton Market district, is a culinary oasis that redefines the cocktail experience. Helmed by renowned chef Grant Achatz and his team, The Aviary transcends traditional notions of mixology, offering guests an immersive journey into the art of cocktail creation.

From the moment you step through the doors of The Aviary, you’re greeted by an ambiance of sophistication and innovation. The sleek, modern decor sets the stage for an unforgettable dining experience, where every detail has been carefully curated to delight the senses.

At the heart of The Aviary’s concept is its inventive approach to cocktails. Gone are the standard menus and predictable drink offerings. Instead, guests are invited to embark on a multi-sensory adventure, where each libation is crafted with precision and creativity.

The Aviary’s cocktail menu showcases the team’s ingenuity. It features diverse concoctions pushing flavor, texture, and presentation boundaries. Each drink, from whimsical twists to avant-garde creations, is a work of art. Beyond drinks, the experience extends to expertly trained staff. They guide guests through tastings, providing insights and enhancing the overall experience.

4. Gibson’s Bar & Steakhouse

Gibson’s Bar & Steakhouse, a legendary institution in Chicago’s culinary landscape, has been setting the standard for exceptional dining since its inception in 1989. In the bustling Near North neighborhood, Gibson’s earns renown for its classic American cuisine, unparalleled hospitality, and timeless ambiance. Stepping through the iconic red awnings transports you to a bygone era of elegance and sophistication.

Warm wood-paneled walls and plush leather booths set the inviting tone. A dimly lit ambiance adds to the refined atmosphere. It’s the perfect setting for a memorable dining experience.

At the heart of Gibson’s culinary offerings is its world-class steak selection. From USDA Prime Angus beef to dry-aged cuts and Wagyu steaks, each hand-cut steak is expertly prepared to perfection, ensuring a melt-in-your-mouth dining experience that’s second to none.

But Gibson’s is more than just a steakhouse. The extensive menu features an array of delectable dishes, including fresh seafood, hearty salads, and indulgent sides, all made with the finest ingredients and executed with precision and care.

5. Drumbar

Drumbar, perched atop the iconic Raffaello Hotel in Chicago’s bustling Gold Coast neighborhood, offers a sophisticated, elevated cocktail experience. With its stylish ambiance, creative libations, and panoramic city skyline views, Drumbar has established itself as a premier destination for discerning cocktail enthusiasts.

As you ascend to Drumbar’s rooftop oasis, you’re greeted by an ambiance that exudes elegance and warmth. The sleek, modern decor is complemented by plush seating, soft lighting, and chic accents, creating an atmosphere that is both inviting and upscale.

But it’s the cocktails that truly steal the show at Drumbar. Helmed by a team of talented mixologists, the cocktail menu features an inspired selection of handcrafted libations that showcase the creativity and artistry of the craft. From classic concoctions with a modern twist to innovative creations that push the boundaries of flavor and presentation, each drink is a work of art in its own right.

meeting rich men in Chicago

6. RPM Steak

RPM Steak, nestled in Chicago’s River North neighborhood, is a culinary gem renowned for its exceptional steaks, elegant ambiance, and impeccable service. Helmed by the renowned restaurateurs behind RPM Restaurants, RPM Steak combines classic steakhouse tradition with modern sophistication to create a dining experience that is both timeless and innovative.

Upon entering RPM Steak, guests are greeted by refined luxury and understated elegance. The sleek, contemporary decor accentuates warm wood tones, soft lighting, and stylish furnishings, creating an inviting and upscale setting.

But it’s the cuisine at RPM Steak that genuinely sets it apart. The menu features a selection of USDA Prime steaks, dry-aged in-house and expertly prepared to perfection. From bone-in ribeyes to filet mignon and porterhouse cuts, each steak is sourced from the finest purveyors and cooked to your desired level of doneness, resulting in an exceptional dining experience.

7. Celeste

Celeste resides in Chicago’s lively River North neighborhood. It’s a culinary and cocktail destination. The venue blends timeless elegance with modern sophistication. Celeste boasts stunning Art Deco-inspired decor. Its innovative cuisine and expertly crafted cocktails ensure an unforgettable experience. Upon entering Celeste, you’re transported to a bygone era of glamour. The meticulously restored interior features intricate architectural details. Luxurious furnishings and plush velvet curtains create an elegant atmosphere.

Celeste’s culinary offerings showcase a creative and eclectic menu inspired by global flavors and seasonal ingredients. Each dish delights the senses as a culinary masterpiece, ranging from inventive small plates and shareable appetizers to expertly prepared mains and decadent desserts.

But it’s not just the food that makes Celeste a standout destination—it’s also the cocktails. Skilled mixologists lead the bar program at Celeste. They craft artisanal cocktails pushing boundaries of flavor and presentation. Whether you enjoy classic concoctions with a twist or innovative creations, Celeste has something for you. Expect drinks that surprise and delight, tantalizing your taste buds.

8. The Violet Hour

The Violet Hour is situated in Wicker Park, Chicago’s vibrant neighborhood. It’s a celebrated cocktail bar known for impeccable drinks and stylish ambiance. Since 2007, it has led Chicago’s cocktail scene with quality and creativity. Step through its unassuming entrance to experience refined elegance. The bar’s interior, with plush seating and vintage decor, exudes old-world charm. Soft candlelight adds to its cozy and sophisticated atmosphere.

At the heart of The Violet Hour’s allure is its expertly crafted cocktails. A team of talented mixologists leads the bar. They offer a menu of innovative libations. These showcase the finest spirits, house-made syrups, and fresh ingredients. Each drink, from timeless classics to inventive concoctions, is a work of art. They’re designed to tantalize the taste buds and captivate the senses.

9. East Bank Club

The East Bank Club, located in Chicago’s dynamic River North neighborhood, is a premier health, fitness, and leisure destination. Since its inception in 1980, the club has been synonymous with luxury, offering members a comprehensive array of amenities and services tailored to their wellness needs.

Spanning over 450,000 square feet, the East Bank Club is more than just a gym—it’s a lifestyle destination. The club features state-of-the-art fitness facilities. These include cardio and strength training areas, group exercise studios, and indoor and outdoor pools. Additionally, there are tennis and basketball courts available. Whether you’re a seasoned athlete or just starting, there are classes and programs for every fitness level.

Beyond fitness, the East Bank Club offers additional amenities to enhance members’ well-being. Relax and rejuvenate at the luxurious spa, featuring a full menu of massage therapies, skincare treatments, and salon services. Unwind with friends or colleagues at the club’s restaurants and bars, offering a selection of gourmet cuisine, craft cocktails, and fine wines. Take advantage of the club’s business and networking opportunities with meeting rooms, event spaces, and exclusive member events.

Read more: MillionaireMatch in Coronado, California

10. SoHo House Chicago

SoHo House Chicago resides in the lively Fulton Market District, embodying creativity, luxury, and hospitality. It’s a private members’ club and boutique hotel. The venue seamlessly merges vintage charm with contemporary elegance. Guests enjoy a unique and immersive experience within a historic industrial building.

Upon entering SoHo House Chicago, guests are greeted by a welcoming and sophisticated ambiance. The club’s stylish decor features eclectic furnishings, vintage artwork, and luxurious finishes, creating a cozy and chic atmosphere.

One of the defining features of SoHo House Chicago is its extensive array of amenities and facilities. The rooftop pool and terrace offer serene views of the city skyline. The fully equipped gym, spa, and screening room cater to members’ needs. Members can work, relax, and socialize in style at the club.

11. The Berkshire Room

The Berkshire Room is located in Chicago’s vibrant River North neighborhood. It’s a renowned cocktail lounge with timeless sophistication and modern flair. Tucked inside the historic ACME Hotel, The Berkshire Room offers an intimate setting. Guests can unwind and indulge in expertly crafted libations there.

Upon entering The Berkshire Room, its sleek and inviting ambiance immediately captivates guests. The lounge’s chic decor features plush leather seating, exposed brick walls, and warm lighting, creating an upscale and inviting atmosphere.

But the cocktails genuinely steal the show at The Berkshire Room. Helmed by a team of talented mixologists, the bar offers a carefully curated menu of inventive and expertly crafted libations. From classic cocktails with a contemporary twist to innovative creations inspired by seasonal ingredients, each drink is a testament to the artistry and creativity of the bartenders.


This guide has highlighted some of Chicago’s top spots for meeting affluent individuals, from upscale restaurants to exclusive cocktail lounges. Explore these venues and follow the tips for better connecting with wealthy men. Enjoy a night at The Berkshire Room or network at the East Bank Club for elite encounters. Approach interactions authentically and confidently for valuable connections. Venture forth enthusiastically, using this guide as your roadmap to success in meeting rich men in Chicago.