Unrivaled Hotels for Sale in Chicago, the Windy City

We checked thousands of reviews on and to find the best hotels for your stay
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Alexandra Sanders

Updated: 07 August 2024 · 7 min

When searching for lucrative investment opportunities, the vibrant city of Chicago stands out with its rich history, cultural diversity, and bustling economy. Among various investment avenues, hotels for sale in Chicago offer unique prospects for both seasoned investors and newcomers looking to delve into the hospitality sector. With its iconic skyline, renowned attractions, and a steady influx of tourists, the Windy City represents a prime location for tapping into the hospitality market.

Chicago's hotel scene is as diverse as its neighborhoods, providing a variety of options tailored to different types of travelers and investors alike. From boutique hotels nestled in the historic districts to larger establishments in the lively heart of downtown, there’s something for every investment strategy. Exploring available hotels for sale in Chicago not only allows you to enter a thriving market but also offers the chance to contribute to the city’s dynamic tourism landscape.

Investing in hotels in this bustling metropolis requires thorough research and understanding of the local real estate trends. By evaluating factors such as location, amenities, and market demand, you can identify the best opportunities that align with your goals. Whether you're considering a complete renovation or seeking a fully operational business, the potential for growth in the Chicago hotel market is undeniable, making it a compelling prospect for any investor.
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Our Top 10

(Sorted by rating & number of reviews)

1. The Westin Chicago River North Hotel
2. Hyatt Regency Chicago Hotel
3. Residence Inn By Marriott Chicago Downtown/River North
4. The Peninsula Chicago Hotel
5. Hampton Inn Chicago Downtown/N Loop/Michigan Ave
6. Four Seasons Chicago Hotel
7. The Palmer House Hilton Hotel
8. The Palmer House Hilton Hotel
9. Hyatt Place Chicago/Downtown - The Loop Hotel
10. Hotel Lincoln

Luxury Hotels for Sale in Chicago

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Chicago
Mar 15, 2026 - Mar 16, 2026

The Westin Chicago River North Hotel

8.6

Good

(131 Reviews)

+ 221 photos
The Westin Chicago River North has earned a reputation as a family-friendly destination in the very heart of downtown. Its prime location along the river allows easy access to family attractions while providing a relaxing retreat after a day of exploration. With amenities like a heated indoor pool and spacious rooms, The Westin stands out in the list of hotels for sale in Chicago that cater to families. The hotel offers various dining options, including a kid-friendly restaurant, which further enhances the guest experience. Families appreciate the thoughtful amenities such as crib rentals and babysitting services, making it a convenient choice. This property combines luxury with family-friendly features, ensuring strong prospective returns for investors.
Address: 320 North Dearborn Street
Rating: Good 8.6 (131 Reviews)
Rooms: 445
Price: From 129$

Hyatt Regency Chicago Hotel

8.5

Good

(2130 Reviews)

+ 371 photos
The Hyatt Regency Chicago is frequently chosen by families due to its spacious rooms and extensive amenities. With its prime location along the banks of the Chicago River, families are just steps away from attractions like the Navy Pier and Millennium Park. The hotel’s offerings include a kid’s club, on-site dining options with children’s menus, and easy access to family-friendly activities, making it a solid candidate among hotels for sale in Chicago. In addition, the Hyatt Regency provides a unique blend of comfort, convenience, and modern aesthetics, ensuring a pleasant experience for both parents and children. Its reputation and extensive offerings make it a leader in family travel. Potential investors will benefit from the property’s strong brand recognition and high occupancy rates, ensuring a solid return.
Address: 151 East Wacker Drive
Rating: Good 8.5 (2130 Reviews)
Rooms: 2019
Price: From 122$

Residence Inn By Marriott Chicago Downtown/River North

8.6

Good

(331 Reviews)

+ 78 photos
The Residence Inn by Marriott Chicago Downtown/River North is an ideal choice for families seeking a home-away-from-home experience. This hotel features spacious suites with kitchenettes, allowing families to prepare their meals during their stay. Its favorable position among hotels for sale in Chicago ensures a solid market presence, appealing to both short- and long-term guests. Families can enjoy a complimentary hot breakfast each morning, as well as easy access to local attractions, parks, and dining options. With amenities geared towards longer stays, like laundry facilities and grocery delivery services, the Residence Inn enhances the experience for families exploring the city. This combination of comfort and convenience makes it an attractive option for investors targeting the family travel market.
Address: 410 North Dearborn Street
Rating: Good 8.6 (331 Reviews)
Rooms: 270
Price: From 179$

Boutique Hotels for Sale in Chicago

Chicago is home to an eclectic array of boutique hotels that provide a unique charm and personalized service, attracting travelers seeking distinctive experiences. These hotels often reflect local culture and history, making them attractive investment options for those interested in the boutique market. Hotels for sale in Chicago within this category not only contribute to the city’s diverse hospitality scene but also appeal to tourists wanting more than just a standard hotel stay. Each boutique property presents an opportunity for investors to create a niche market while benefiting from Chicago's thriving tourism sector. With an accent on individuality and character, the following boutique hotels could be prime acquisitions in this flourishing market.

The Peninsula Chicago Hotel

9.4

Good

(241 Reviews)

+ 269 photos
The Peninsula Chicago stands as a symbol of luxury and sophistication, attracting discerning guests from diverse backgrounds. This hotel is known for its lavish rooms and exceptional service, making it a standout investment in the hotels for sale in Chicago market. The Peninsula offers innovative dining options, a luxurious spa, and a rooftop pool, which enhance its appeal to prospective buyers. Located in the very heart of downtown, the hotel is close to major attractions like the Magnificent Mile and cultural institutions, ensuring constant visitor interest. Its reputation for excellence creates a loyal clientele, offering stability for investors. Owning The Peninsula would be an ideal move for those interested in a prestigious hotel investment.
Address: 108 East Superior Street
Rating: Good 9.4 (241 Reviews)
Rooms: 257
Price: From 428$

Hampton Inn Chicago Downtown/N Loop/Michigan Ave

7.9

Good

(1191 Reviews)

+ 106 photos
The Hampton Inn Chicago Downtown/N Loop/Michigan Ave offers affordability and convenience in a prime downtown location. With comfortable rooms and complimentary amenities like breakfast and Wi-Fi, this hotel appeals to budget-conscious travelers seeking a central lodging option. Its relative positioning among hotels for sale in Chicago highlights its popularity among tourists wanting a blend of quality and price. Guests appreciate the hotel’s focus on cleanliness and customer service, often resulting in repeat visits. With easy access to public transportation and various attractions, the Hampton Inn serves as an excellent base for city exploration. Investing in this hotel offers a solid potential for returns from a diverse clientele.
Address: 68 E. Wacker Place
Rating: Good 7.9 (1191 Reviews)
Rooms: 143
Price: From 259$

Four Seasons Chicago Hotel

9.0

Good

(171 Reviews)

+ 225 photos
Located on the prestigious Magnificent Mile, the Four Seasons Hotel Chicago redefines luxury with its stunning accommodations and top-tier amenities. This hotel provides an exquisite blend of vibrant city life and tranquil retreats, appealing to both leisure and business travelers. With the growing interest in hotels for sale in Chicago, the Four Seasons is an attractive investment given its high occupancy rates and loyal customer base. The hotel features a renowned restaurant, an expansive spa, and versatile meeting spaces, ensuring a comprehensive experience for guests. Its prime location places it within walking distance to famous attractions, shopping, and dining. Investing in the Four Seasons could yield significant returns, given its consistent demand and esteemed brand.
Address: 120 East Delaware Place
Rating: Good 9.0 (171 Reviews)
Rooms: 345
Price: From 730$

Family-Friendly Hotels for Sale in Chicago

Families traveling to Chicago will look for accommodations that cater to their unique needs, such as spacious rooms, amenities for children, and convenient access to family-oriented attractions. The family-friendly hotels for sale in Chicago provide a welcoming atmosphere where guests can enjoy their stay without sacrificing comfort or convenience. These hotels often feature kid-focused services and programs, making them highly sought-after by families visiting the vibrant city. Investing in family-friendly hotels allows for stability in occupancy rates and can attract repeat visitors looking for an enjoyable getaway. Below are some excellent options for those interested in this area of the hospitality market.

The Palmer House Hilton Hotel

7.5

Good

(969 Reviews)

+ 216 photos
The Palmer House Hilton is one of Chicago’s oldest and most revered hotels, with a history dating back to 1871. This grand establishment offers guests a chance to experience the elegance of a bygone era while enjoying modern amenities. As one of the most notable hotels for sale in Chicago, its rich history and stunning architecture provide a unique appeal for both leisure and business travelers. The Palmer House features luxurious accommodations, a lavish ballroom, and a full-service spa, making it a top choice for events and stays alike. The hotel’s central location provides easy access to key attractions, ensuring a high volume of visitors year-round. Investors will benefit from the hotel’s storied legacy and strong brand recognition, making it a valuable addition to any portfolio.
Address: 17 East Monroe Street
Rating: Good 7.5 (969 Reviews)
Rooms: 1641
Price: From 89$

The Palmer House Hilton Hotel

7.5

Good

(969 Reviews)

+ 216 photos
While already noted for its historical significance and luxury, the Palmer House Hilton also excels as an event venue with its extensive facilities. Featuring over 130,000 square feet of functional space, this iconic hotel hosts a wide range of events, from corporate meetings to weddings. For investors interested in hotels for sale in Chicago with strong event capabilities, Palmer House Hilton combines elegance with practicality. Its stunning ballrooms, adorned with vintage charm and updated technology, provide a captivating backdrop for any event. The hotel's central location and rich history further enhance its appeal, ensuring that it remains a top choice for event planners. Owning this historic hotel offers the opportunity to build on its legacy while tapping into Chicago’s vibrant events market.
Address: 17 East Monroe Street
Rating: Good 7.5 (969 Reviews)
Rooms: 1641
Price: From 89$

Hyatt Place Chicago/Downtown - The Loop Hotel

8.2

Good

(4986 Reviews)

+ 87 photos
Hyatt Place Chicago/Downtown - The Loop has made significant strides in adopting sustainable practices while providing comfortable accommodations in a bustling urban environment. The hotel focuses on energy-efficient lighting, responsible sourcing of food products, and waste reduction programs. As part of the family of hotels for sale in Chicago, this property is well-positioned to cater to eco-conscious travelers. It features spacious guest rooms, a fitness center, and a rooftop lounge—all designed with eco-friendly practices in mind. Located near the city's top attractions, the hotel's commitment to sustainability attracts environmentally-aware visitors seeking a modern hotel experience. The potential for revenue growth is strong as interest in eco-friendly hotels continues to rise among travelers.
Address: 28 North Franklin Street
Rating: Good 8.2 (4986 Reviews)
Rooms: 206
Price: From 125$

Historic Hotels for Sale in Chicago

Chicago boasts a wealth of historic hotels that offer not only a place to stay but also a glimpse into the city’s rich architectural and cultural heritage. These iconic establishments provide a unique atmosphere, often featuring timeless design elements and a storied past. Investing in historic hotels for sale in Chicago presents an opportunity to capitalize on the nostalgia and charm that attract visitors keen on experiencing the city’s history. These hotels often host cultural events and activities that deepen their roots within the community. Below are several historic properties that stand out as prime investments for those interested in the heritage hospitality market.

Hotel Lincoln

+ 13 photos
Hotel Lincoln offers a charming blend of history and modern comfort in a prime location near Lincoln Park. Famed for its quirky design and eco-friendly practices, this boutique hotel caters to travelers who appreciate creative spaces and local flavor. The growing interest in hotels for sale in Chicago makes Hotel Lincoln an appealing opportunity due to its popularity among both locals and tourists. Its rooftop bar boasts stunning views of the park and skyline, attracting a vibrant social scene, while its commitment to showcasing local art adds to the guest experience. The hotel's prime location allows for easy access to nearby attractions, enhancing its appeal. With a strong online presence and loyal customer base, Hotel Lincoln promises potential profitability for investors.
Address: 1816 North Clark Street
Rooms: 184
Price: From 110$

The Drake Hotel

8.0

Good

(587 Reviews)

+ 227 photos
The Drake Hotel is an iconic Chicago landmark often sought by travelers for its historic charm and premium location along Lake Michigan. Known for its luxurious accommodations and fantastic dining options, The Drake has hosted countless dignitaries and celebrities over the years. Its standing as one of the premier hotels for sale in Chicago presents an exceptional investment opportunity with solid returns due to its continued popularity. The hotel combines classic style with modern comforts, featuring beautifully appointed rooms and a renowned afternoon tea service. Its prime location near renowned attractions and stunning lake views adds to its allure for both tourists and event organizers. Owning The Drake would allow investors to partake in a piece of Chicago's rich history while benefiting from the ongoing demand for luxury accommodations.
Address: 140 East Walton Place
Rating: Good 8.0 (587 Reviews)
Rooms: 535
Price: From 149$

The Langham Chicago Hotel

9.3

Good

(343 Reviews)

+ 157 photos
The Langham, Chicago, is a five-star hotel that epitomizes luxury with its elegant design and first-class service. Situated along the Chicago River, this hotel features spacious guest rooms with stunning views of the skyline and river. Investing in the Langham aligns perfectly with the hotels for sale in Chicago due to its established brand reputation and strong occupancy rates. The hotel boasts award-winning dining options, a world-class spa, and exceptional event spaces, making it a premier choice for corporate and social gatherings. With an ideal location near major attractions, including Millennium Park and the Art Institute, the Langham attracts a constant flow of tourists. Its luxurious offerings ensure long-term profitability for potential investors.
Address: 330 North Wabash Avenue
Rating: Good 9.3 (343 Reviews)
Rooms: 316
Price: From 366$

Eco-Friendly Hotels for Sale in Chicago

As sustainability becomes a primary concern for travelers, eco-friendly hotels are emerging as a significant segment in the Chicago hospitality market. These hotels prioritize environmentally conscious practices while providing luxurious accommodations and services. Investing in eco-friendly hotels for sale in Chicago allows buyers to cater to a growing demographic of eco-conscious tourists seeking responsible travel options. With features such as energy-efficient operations, sustainable design, and local sourcing of materials, these hotels not only help protect the environment but also present unique selling propositions. Below are a few noteworthy eco-friendly hotels that reflect Chicago's commitment to sustainability.

The Robey, Chicago, A Member Of Design Hotels

8.6

Good

(330 Reviews)

+ 100 photos
The Robey, located in the historic Logan Square neighborhood, is a modish boutique hotel known for its stylish decor and innovative offerings. Housed in a landmark building, the hotel features a rooftop lounge with breathtaking views, drawing in guests year-round. Its unique positioning within the hotels for sale in Chicago market lies in its ability to cater to a trendy demographic, tapping into Chicago’s vibrant arts and culture scene. The Robey blends sophisticated aesthetics with relaxed hospitality, making it a favorite among creative professionals and visitors looking for something authentic. Its proximity to eclectic dining options and local hotspots enhances its desirability for both travelers and event planners. This trendy establishment is an excellent option for investors seeking a boutique hotel experience with a thriving atmosphere.
Address: 2018 W North Avenue
Rating: Good 8.6 (330 Reviews)
Rooms: 89
Price: From 144$

Holiday Inn Express Chicago - Magnificent Mile, An Ihg Hotel

7.6

Good

(225 Reviews)

+ 97 photos
The Holiday Inn Express Chicago – Magnificent Mile is a reliable choice for travelers who want a comfortable stay without breaking the bank. Situated near Chicago's renowned shopping district, the hotel caters to visitors looking for convenience and accessibility. As one of the prominent hotels for sale in Chicago, it offers modern amenities, including complimentary breakfast and fitness facilities, designed with the budget traveler in mind. The location provides easy access to major attractions, making it attractive to both leisure and business tourists. Its reputation for affordability and quality service promotes higher guest turnover, ensuring consistent occupancy levels. Investors can feel confident with this hotel, tapping into the budget-conscious market while profiting from strategic positioning.
Address: 640 North Wabash Avenue
Rating: Good 7.6 (225 Reviews)
Rooms: 174
Price: From 69$

Conference and Event Hotels for Sale in Chicago

Chicago is known for hosting a range of events, from corporate meetings to lavish weddings, making conference and event hotels a lucrative niche in the hospitality industry. These hotels are strategically designed with extensive meeting spaces and event planning services to meet the needs of business and leisure travelers alike. Investing in conference hotels for sale in Chicago allows investors to tap into the thriving MICE market. With well-appointed ballrooms, state-of-the-art technology, and convenient locations, these hotels play a vital role in the city’s event landscape. Here are several hotels well-suited for hosting events and conferences that represent promising investment opportunities.

Budget-Friendly Hotels for Sale in Chicago

For travelers on a budget, affordability combined with quality is essential when selecting accommodations. Chicago's budget-friendly hotels meet this need and can cater to a diverse audience, from families to solo travelers exploring the city. Investing in budget-friendly hotels for sale in Chicago provides the chance to capture a significant segment of the market, appealing to a growing number of cost-conscious visitors. These hotels often feature essential amenities without sacrificing comfort, intertwining accessibility with thoughtful service. Here are some notable budget-friendly options to consider in this vibrant city.