Luxury Haunts: Top Places to Meet Rich Men in Chicago
12 mins read

Luxury Haunts: Top Places to Meet Rich Men in Chicago

Chicago is known for its skyscrapers, art, music, and sports teams. It is also home to a large population of successful, wealthy men. If you are looking to meet rich men in Chicago, there are several places you can go to increase your chances of success.

Chicago is one of the most vibrant and diverse cities in the United States and has many successful and wealthy men with a bustling business district, high-end restaurants, and exclusive clubs and bars. There are plenty of opportunities to meet rich men in Chicago. The city’s rich cultural and arts scene and world-renowned museums and galleries make it an attractive destination for the affluent.

Top places to meet rich men in Chicago

1. Dating Apps

Due to their hectic schedules, rich men in Chicago use dating apps quite frequently. These platforms offer a convenient way to navigate their social lives, catering to their need for flexibility and a diverse pool of potential partners. Given the emphasis on making meaningful connections in a less traditional setting, being mindful of how to engage on these apps is vital.

Starting conversations with a unique and engaging approach is vital. A generic opener might not capture the attention of these busy professionals. Opt for something original, like a creative icebreaker or a personalized comment demonstrating genuine interest. Doing so sets a more engaging tone for conversation and can significantly increase the chances of making a memorable first impression.

Recognize the demands of your lifestyle to navigate dating apps in Chicago effectively. Seize the opportunities dating apps present to connect with successful men in the city. Being proactive is vital to standing out in a sea of messages on dating platforms.

Initiate conversations with a personable approach to make your interactions memorable. Stand out by ensuring your messages are engaging and distinctive from the competition.

Some popular dating apps include:

  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 a historic building in downtown Chicago, Illinois, USA. Initially constructed in 1893, it served as a private club for athletes and sports enthusiasts, holding the distinction of being one of the city’s most prestigious clubs at the time. The building’s design is a stunning example of the Venetian Gothic style, which was popular in the late 19th century.

Over the years, the Chicago Athletic Association has hosted various events for different purposes. In the early 20th century, business people frequently gathered and socialized at the venue. During World War II, it temporarily housed soldiers in barracks. However, in the 1970s, the building fell into disrepair and eventually closed.

The restoration project aimed to preserve the historic architecture of the building while adding modern amenities and features to make it a comfortable and luxurious place to stay. The hotel now offers guest rooms, restaurants, bars, and event spaces. All while maintaining the character and charm of the original building.

rich men in Chicago

3. The Aviary

The Aviary is a high-end cocktail bar and restaurant in Chicago, Illinois, USA. Grant Achatz and Nick Kokonas, who own the Michelin-starred restaurant Alinea, opened The Aviary in 2011. The Aviary is renowned for its innovative and experimental approach to cocktail making, employing techniques such as molecular gastronomy and incorporating unusual ingredients and flavors. The bar’s menu is divided into different sections, each delivering a unique experience. For example, the “Kitchen” section features cocktails made with culinary techniques and ingredients, while the “Bubble Room” section offers carbonated or foam drinks.

One of the most popular drinks at The Aviary is the “In the Rocks” cocktail, served in a glass carved from a single block of ice. The drink is made by pouring a mixture of bourbon, vermouth, and bitters into the ice sphere. Which slowly melts as the drink is enjoyed, creating a unique flavor profile.

In addition to its cocktail menu, The Aviary offers a small selection of dishes, including small plates and desserts. The restaurant’s interior is sleek and modern, with a minimalist design that allows cocktails to take center stage.

4. Chicago Symphony Orchestra

The Chicago Symphony Orchestra, often CSO, is a renowned symphony orchestra based in Chicago, Illinois. It is considered one of the top orchestras in the world and has a long and storied history of musical excellence. The orchestra has played a vital role in shaping Chicago’s cultural identity and is a source of inspiration and artistic innovation.

The Chicago Symphony Orchestra was founded in 1891 by Theodore Thomas, a distinguished conductor who sought to establish a world-class ensemble in Chicago. Thomas’s vision was to create an orchestra rivaling the best orchestras in Europe. Under his leadership, the CSO quickly gained recognition for its exceptional performances and repertoire.

Over the years, the CSO has been led by many distinguished conductors, including Frederick Stock, Sir Georg Solti, and Daniel Barenboim. These leaders have left an indelible mark on the orchestra’s legacy, further solidifying its reputation for musical excellence.

The Chicago Symphony Orchestra is a cultural treasure, not only for the city of Chicago but also for the global music community. Its rich history, exceptional musicians, and dedication to musical innovation continue to make it a source of inspiration and artistic achievement. Whether you’re a lifelong classical music enthusiast or a newcomer to orchestral music, the CSO’s performances are a must-experience cultural delight in the Windy City.

Exclusive Clubs and Bars

Exclusive clubs and bars are the perfect places to start if you want a sophisticated environment to meet wealthy men. These venues offer a luxurious atmosphere and attract a high-end clientele. Some of Chicago’s top exclusive clubs and bars include the Soho House, The Drake Hotel, and the Waldorf Astoria.

1. Gibson’s Bar & Steakhouse

Gibson’s Bar & Steakhouse is a classic American steakhouse in Chicago, Illinois, USA. It was founded in 1989 and has become one of the city’s most popular and well-known steakhouses.

The restaurant offers a variety of high-quality steaks, including filet mignon, New York strip, ribeye, and porterhouse, all aged for at least 40 days to enhance their flavor and tenderness. In addition to steaks, the menu also features seafood, salads, sandwiches, and other classic American dishes.

Gibson’s Bar & Steakhouse earned its reputation for fostering a lively and energetic atmosphere, drawing in a crowd of locals and tourists, filling the bustling bar and packed dining room. The restaurant’s interior is classic and timeless, with dark wood paneling, leather booths, and vintage decor.

One of Gibson’s signature dishes is the “Gibson’s Martini.” It is served in a chilled martini glass and garnished with blue cheese-stuffed olives. The restaurant also offers an extensive wine list featuring worldwide reds, whites, and sparkling wines.

2. Drumbar

Drumbar is a rooftop lounge and bar in Chicago, Illinois, USA. It is situated on the 18th floor of the Raffaello Hotel and offers stunning views of the city’s skyline.

The bar has a speakeasy vibe, with a cozy and intimate interior featuring leather couches, dim lighting, and a fireplace. In addition to the indoor seating, Drumbar has an outdoor terrace with comfortable seating and a fire pit, making it the perfect spot to enjoy a drink on a warm summer night.

Drumbar’s cocktail menu features a variety of classic and modern cocktails, all made with high-quality ingredients and expertly crafted by the bar’s skilled mixologists. The bar is known for its extensive whiskey selection, including rare and hard-to-find bottles worldwide. One of the most popular drinks at Drumbar is the “Smoke Signal,” made with mezcal, grapefruit, honey, and lime.

3. RPM Steak

RPM Steak is a modern steakhouse in downtown Chicago, Illinois, USA. It is part of the RPM Hospitality group, including other popular dining destinations such as RPM Italian and RPM Seafood.

RPM Steak offers a contemporary take on the classic American steakhouse. It features high-quality meats and seafood, creative side dishes, and a world-class wine list. The restaurant’s menu includes a variety of steak cuts, such as filet mignon, ribeye, and wagyu beef, all prepared to the diner’s preferred temperature.

In addition to its steaks, RPM Steak offers an extensive seafood selection, including raw bar items like oysters and shellfish platters and cooked seafood dishes like grilled octopus and Dover sole.

The interior of RPM Steak is sleek and modern, with a mix of leather banquettes, dark wood accents, and contemporary artwork. The restaurant also features an outdoor patio, perfect for al fresco dining during the warmer months. A team of expert sommeliers curates the restaurant’s extensive wine list and features over 500 selections worldwide, making it a destination for wine enthusiasts.

4. Celeste

Celeste is a bar and restaurant in the River North neighborhood of Chicago, Illinois, USA. The establishment occupies a historic building dating back to the 1880s. The building has undergone restoration to return to its former glory, retaining classic details such as exposed brick walls, hardwood floors, and ornate ceilings.

The menu at Celeste features modern American cuisine, focusing on seasonal ingredients and creative flavor combinations. The dinner menu includes small plates such as beef tartare, crab cakes, roasted bone marrow, and entrees like roasted chicken, grilled steak, and seared salmon.

The cocktail menu features classic drinks like the Old Fashioned and the Manhattan and creative and unique creations like the “Cinnamon Toast Punch” and the “Maple Fashioned.”

In addition to its dining and drinking options, Celeste also features a rooftop terrace that offers stunning city skyline views. The rooftop is open year-round, with a retractable glass roof and heaters to keep patrons warm during the colder months.

The ambiance at Celeste is upscale and sophisticated, with a mix of vintage and modern decor elements. The bar features plush leather seating, elegant light fixtures, and a cozy fireplace, creating a warm and inviting atmosphere.

5. The Violet Hour

“The Violet Hour” is a distinguished cocktail lounge in Chicago, Illinois. Known for its chic and sophisticated atmosphere, this cocktail bar has earned a reputation as one of the city’s premier destinations for craft cocktails and a unique mixology experience. The bar takes its name from a line in T.S. Eliot’s poem “The Waste Land” and reflects the literary and artistic inspirations that underpin its creative cocktail offerings.

When patrons enter ‘The Violet Hour,’ they encounter an ambiance that exudes elegance and intimacy. Plush seating, dim lighting, and contemporary art adorn the lounge’s interior, creating an upscale and welcoming environment for patrons.

The lounge’s serene atmosphere draws those seeking an escape from the city hustle. The Violet Hour boasts an extensive cocktail menu, from classics to innovative creations. Indulge in bar bites like charcuterie and cheese plates at The Violet Hour.

At the bar, savor decadent desserts such as chocolate mousse and cheesecake. The Violet Hour pays attention to detail and uses high-quality ingredients in its food offerings.

One unique aspect of The Violet Hour is its policy of no cell phones or photography inside the bar. This creates a more intimate and social atmosphere. Encouraging patrons to focus on their cocktails and conversations rather than their screens.


Meeting rich men in Chicago is not difficult if you know where to look. Exclusive clubs and bars, fine dining restaurants, luxury hotels, high-end gyms, fitness centers, charity events and galas, and cultural and art events are all great places to meet wealthy men. Remember to dress to impress, be confident, and be approachable. With these tips, you will find the man of your dreams in Chicago.