The Most Expensive Condo Buildings in Chicago

To experience living in the lap of luxury in one of the most dynamic cities in the world, take a dive into the most expensive condo buildings Chicago has to offer. These one-of-a-kind residences are stunning with their elegant designs, exquisite locales and list of extravagant amenities. One has only to step inside to get a taste of what makes these spectacular locations the most coveted in all of Chicago. 

Park Tower

Built in 2000, this multi-use 73-story skyscraper is centrally located on the Magnificent Mile, a world-famous strip of prestigious hotels and shopping along Chicago’s Michigan Avenue. Floors 56 to 70 at Park Tower hold private luxury condominiums. Two-bedroom condos at Park Tower start at approximately 2,000 square feet and go for roughly $1.3M, stretching to 8,400 square foot five-bedroom penthouse condos priced over $10M. These units provide private outdoor terraces and offer stunning views of both the lake and the city from multiple vantage points. This full-amenities building offers an indoor pool, ultra-modern gym as well as spa services, a 24-hour staff, onsite manager and concierge, and the famous Nomi Restaurant.

St. Regis Chicago

Known as St. Regis Residences, this skyscraper was designed by renowned chief architect Jeanne Gong in 2016 and completed in 2020. The development comprises three connected shimmering towers, the tallest of which rises to a dazzling 101 stories. Meticulously and thoughtfully designed to create a mixture of elegance, modernity and ease, the 393 unique St. Regis condos range from 1,050 square foot one-bedroom units to five-bedroom penthouses. The structure stands at the crossroads of The Chicago River and Lake Michigan and is part of the award-winning Lakeshore East neighborhood. Everything one could want, from casual to fine dining, world-class parks, theaters and museums, all surround this magnificent residence. Prices range roughly from $930k to $11.5M, with one penthouse selling for a stunning $20.6M in 2022.

One Bennett Park

Located in a premiere neighborhood on the northside of Chicago, One Bennett Park boasts exclusive lakefront and beach access as well as private access to the beautiful two-acre Bennett Park. The famed Art Institute of Chicago, The Museum of Contemporary Art and theaters are all within walking distance of this distinguished structure, designed by acclaimed architect, Robert A.M. Stern. Features include a landscaped terrace with pool and lounge area, eco-friendly valet dry cleaning, on-site pet grooming and veterinary service, and a state-of-the-art fitness club. The three-to-four bedroom units start at $2.3M and range to $6.5M with the penthouse peaking at a whopping $15.5M. Sizes vary widely from between 3,500 to 7,500 square feet.

One Chicago

Right at the corner of State Street and Chicago stands the regal One Chicago, which offers some of the area’s most elegant luxury condos. The One Chicago Apartments, 23 West Apartments and 23 West Lofts all share a complimentary membership to Life Time Fitness, on-site valet parking, and a rooftop terrace with outdoor pool, grilling stations and cabanas. One-bedroom units start in the low $1M and penthouse units with three bedrooms and five bathrooms soar into the high $13M. In this mega-luxury-complex, you can find something anywhere in between that is sure to meet your every need.

Tribune Tower

For those looking for lavish terraces and soaring ceiling heights, combined with other stunning architectural details at the heart of Chicago’s urban center, The Tribune Tower will be a slice of heaven. Connecting the refined Gold Coast with the trendy, artistic River North, this elegant structure wears its history proudly, while bringing modern interpretations into play. Custom-designed cabinetry alongside state-of-the-art appliances, add to the functionality of this classic space. Residences range from one-bedrooms to four-bedrooms and are priced between roughly $839k to $4.9M.

The Palmolive

The Palmolive is an historic 37-floor art deco building that was built and completed in 1929 by the architectural firm Holabird & Root. Formerly the Playboy Mansion, it is currently home to one, two and three-bedroom condos. Condo buyers can expect plantation shutters throughout, dark oak floors, elaborate moldings, marble countertops and modern appliances. Residents can enjoy a fitness center replete with sauna and whirlpool, the Beacon Club, as well as valet parking. Condos at The Palmolive tend to range in size from 1,200 square feet to 5,400 square feet, and their one bedroom residences typically start at $500k ranging up to three-bedrooms priced at $6M.