We have created a list with cool, unusual and unique hotels in Chicago, USA. We have also included accommodation in apartments, holiday homes, boutique hotels, historic buildings, guest houses, romantic hotels and villas. Hope you enjoy it. We think it might be the best of its kind around. Tip: Set your dates to see room prices!
A list by Ella Hofer & Maryna Kravets. Updated March 2024.
Apartment hotel.Great location. Located in the heart of downtown Chicago, just 3 blocks away from the Magnificent Mile, this self-catering apartment features a balcony with iconic views of the city. Free WiFi access is available. Floor-to-ceiling windows frame the fireplace in the 2-bedroom apartment at The Penthouse at Grand Plaza. Along with a fully-equipped kitchen and 3 full bathrooms, the apartment includes a dining area, laundry facilities and 3 separate balconies. A rooftop swimming pool and sun deck are provided at Grand Plaza Chicago Penthouse. Guests can make use of the fitness centre and basketball court or shop for essentials at the on-site market. Navy Pier and scenic Millennium Park are both less than a mile away from the hotel.Show full description
This apartment hotel has a great location in Chicago.
Boutique hotel.Charming. Popular among women. Featuring suites with gourmet kitchens and an on-site fitness centre, The Guesthouse Hotel is located in Chicago. Montrose Beach, on Lake Michigan, is 2.8 km away. At The Guesthouse Hotel you will find boutique shopping that features local artists and designers, a 24-hour front desk, and a mini-market. Free WiFi access is available. Each suite features a flat-screen TV, high ceilings, and a private balcony at the Chicago Guesthouse Hotel. A washer and tumble dryer is also included. There is barbecue facilities on each balcony. Other facilities offered at the property include meeting facilities and a shared lounge. The hotel is 1.8 miles from Wrigley Field, 2.4 miles from DePaul University - Lincoln Park Campus and a 10-minute drive away from Lincoln Park Zoo. Chicago O'Hare International Airport is 20 km away.Show full description
Bed and Breakfast.Creative. Great value. Popular among couples. Located near numerous restaurants and shops in the Bucktown neighbourhood of Chicago, Ray's Bucktown features a communal sauna, free WiFi, and in-room breakfast service. Live entertainment at the Congress Theatre is 800 metres away. Each uniquely designed room includes hardwood floors and a flat-screen cable TV at Ray's Bucktown Bed and Breakfast. Free toiletries and a hairdryer are included as well. Select rooms include a spa bath. At Ray's Bucktown Bed and Breakfast you will find a summer herbs garden and several community areas where guests can relax. The property offers free parking and laundry facilities. The bed and breakfast is 2.2 km from DePaul University - Lincoln Park Campus, 3.7 km from Wrigley Field and 3.9 km from Lincoln Park Zoo. Chicago O'Hare International Airport is 19 km away. We are dog friendly and a fee will apply, sorry no cats! . Show full description
I think this is the most CREATIVE bed and breakfast in Chicago.
Bed and Breakfast.Delightful property. Lovely surroundings. Popular among couples. Located in the heart of Lincoln Park’s shopping and dining district, this modernized Chicago B&B features a private grotto and garden with BBQ facilities. Each romantic guest room is equipped with free Wi-Fi. A flat-screen TV is included in every elegant room at Villa D’Citta. Decorated in Italian-inspired décor, each room provides large windows with neighborhood views. A sun deck with a hot tub is available on site at Lincoln Park Villa D’Citta. Daily continental breakfast and gourmet kitchen access is offered to all guests, and a hot breakfast is served on weekends. Bicycles are available for rent on site. The Lincoln Park Zoo is 15 minutes’ walk from this bed and breakfast. The famous Magnificent Mile is 4 miles away.Show full description
Based on my research this is the most beautiful and relaxing bed and breakfast in Chicago.
Bed and Breakfast.Very cosy. Great views. Popular among couples. The Sono Chicago is located in The Old Town neighborhood of Chicago. Lincoln Park Zoo is only 1.2 km away. Parking is free with permit provided by The Sono Chicago. The rooms are fitted with a flat-screen TV with premium cable channels. Each room has an en suite bathroom with a large shower. A complimentary continental breakfast is provided daily. The Magnificent Mile is located within 2 km of The Sono Chicago. Both O'hare and Midway International Airports are within 30 minutes' drive of the property.Show full description
Guest House.Romantic. Great value. Set 1.6 km from Foster Beach, Magnolia Studios offers air-conditioned accommodation with a patio. Complimentary WiFi is offered throughout the property and private parking is available on site. The property offers allergy-free units and is situated 1.8 km from Loyola University Chicago. Featuring a fully equipped kitchen with an oven and a microwave, each unit also comes with a satellite flat-screen TV, ironing facilities, desk and a seating area. A toaster, a fridge and stovetop are also available, as well as a coffee machine. At the guest house, the units include bed linen and towels. Guests at the guest house can enjoy cycling nearby, or make the most of the garden. Wrigley Field is 6 km from Magnolia Studios, while Lincoln Park Zoo is 8.9 km from the property. The nearest airport is Chicago O'Hare International Airport, 22 km from the accommodation.Show full description
I think this is the most ROMANTIC guest house in Chicago. It also has great affordability and beautiful surroundings.
Bed and Breakfast.Charming. Great location. Popular among women. Just 6 miles south of the Chicago city centre, this Bridgeport B&B is 3 minutes’ drive from U.S. Cellular Field, home of baseball’s White Sox. A flat-screen cable TV is provided in each unique suite at Bridgeport Bed and Breakfast. Featuring an on-site restaurant, each suite includes free internet access. A full-size refrigerator is offered, and each room is equipped with fingerprint security locks. Polo Café is located on site and serves American fare for brunch, lunch, and dinner. Guests of Bridgeport B&B will enjoy a breakfast voucher during their stay. Free parking is available at Bed and Breakfast Bridgeport. Banquet space is also offered at this property. Free shuttle service to McCormick Place and nearby train stations is available. McCormick Place is 4 miles away. The Illinois Institute of Technology can be reached in 6 minutes’ drive.Show full description
I think this is one of the most charming, elegant and historic bed and breakfasts in Chicago! WOW!
Luxury Hotel.Newly opened, February 2024. NVCLL Chicago is ideally located in the centre of Chicago, and offers free bikes, free WiFi and a seasonal outdoor swimming pool. This 5-star hotel offers a 24-hour front desk. Private parking is available on site. The hotel will provide guests with air-conditioned rooms offering a desk, a kettle, a fridge, a dishwasher, a safety deposit box, a flat-screen TV, a terrace and a private bathroom with a shower. All guest rooms will provide guests with an oven. Popular points of interest near NVCLL Chicago include Ohio Street Beach, Oak Street Beach and Water Tower Chicago. The nearest airport is Midway International Airport, 19 km from the accommodation.Show full description
Boutique hotel.Hip. Superb interior design. Popular among couples. Situated alongside the shopping, dining and entertainment of the famed Magnificent Mile, this boutique hotel is located in downtown Chicago and offers on-site dining and expansive meeting space. Featuring modern décor and hardwood floors, every room at Hotel EMC2, Autograph Collection provides a 49-inch flat-screen TV with premium cable channels and a coffee maker. Guests can take in the artistic, creative atmosphere of the hotel while enjoying a crafted cocktail at The Albert Tavern, which offers seasonal cuisine for lunch and dinner. A work desk and safety deposit box are also included. Plated breakfast items are also offered at the hotel and room service. A fitness centre and valet dry-cleaning services are offered at EMC2 Hotel. Free WiFi is available in the lobby and public areas. Navy Pier and Millennium Park are both 1 mile away from the hotel. Oak Street Beach is a 15-minute walk away.Show full description
This is likely one of the coolest, most well designed and stylish boutique hotels in Chicago! It also has an amazing hotel bar. WOW!
Apartment. Set in Chicago, 1.2 km from Field Museum of Natural History and 1.9 km from Art Institute of Chicago, 3BR Luxury Glass Apartment With Views Pool & Gym offers air conditioning. Featuring a lift, this property also provides guests with an outdoor pool. Offering free WiFi throughout the property, the non-smoking apartment features a fitness centre. The 3-bedroom apartment is fitted with a living room with a TV with cable channels, a fully equipped kitchen with a dishwasher and an oven, and 2 bathrooms with a hair dryer. Towels and bed linen are featured in the apartment. The accommodation offers a fireplace. Popular points of interest near the apartment include Chicago Symphony Orchestra, DePaul University and Buckingham Memorial Fountain. The nearest airport is Midway International Airport, 16 km from 3BR Luxury Glass Apartment With Views Pool & Gym.Show full description
Apartment.Historic. Lovely interior design. Located in Chicago, 2.2 km from Oakwood Beach and 3.9 km from Guaranteed Rate Field, Forrestville Ave Large Suite provides accommodation with free WiFi in a historic building. Housed in a building dating from 19th century, this apartment is 5.3 km from Museum of Science and Industry - Chicago and 7.2 km from Field Museum of Natural History. The air-conditioned apartment consists of 2 bedrooms, a living room, a fully equipped kitchenette with a microwave and a coffee machine, and 1 bathroom with a bath and a hair dryer. Towels and bed linen are provided in the apartment. The accommodation offers full-day security and private check-in and check-out for guests. This apartment is allergy-free and non-smoking. Guests at the apartment will be able to enjoy activities in and around Chicago, like pub crawls. Adler Planetarium & Astronomy Museum is 8.1 km from Forrestville Ave Large Suite, while DePaul University is 8.4 km away. The nearest airport is Midway International Airport, 13 km from the accommodation.Show full description
Holiday Home.Newly opened, April 2024. Located in Chicago, 1.7 km from Oak Street Beach and 1.9 km from Fullerton Beach, Beautiful Remodeled Penthouse Unit in Old Town offers air conditioning. The property is around less than 1 km from Lincoln Park Zoo, 2.2 km from 360 Chicago and 2.3 km from Water Tower Chicago. Chicago Museum of Contemporary Art is 2.6 km from the holiday home, while Shops at Northbridge is 3.2 km away. The nearest airport is Midway International Airport, 20 km from Beautiful Remodeled Penthouse Unit in Old Town. Free WiFi is available throughout the property and North Avenue Beach is less than 1 km away. The spacious holiday home comes with 3 bedrooms, a TV and a fully equipped kitchen that provides guests with a dishwasher, an oven, a washing machine, a microwave and a fridge. Towels and bed linen are featured in the holiday home. For added privacy, the accommodation features a private entrance.Show full description
Apartment. Located in Chicago, 1.4 km from Union Station and 1.9 km from United Center, 3BR Elegant Glass Penthouse Pool With Deck & Gym offers air conditioning. Featuring a lift, this property also provides guests with an outdoor pool. Providing free WiFi throughout the property, the non-smoking apartment has a fitness centre. The spacious apartment features 3 bedrooms, a TV with cable channels, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 2 bathrooms with a bath. Towels and bed linen are provided in the apartment. Willis Tower is 1.7 km from the apartment, while CIBC Theatre is 2.2 km away. The nearest airport is Midway International Airport, 17 km from 3BR Elegant Glass Penthouse Pool With Deck & Gym.Show full description
Apartment. Situated within 2.5 km of Union Station and 2.7 km of Water Tower Chicago in Chicago, Presidential Penthouses w the best View- Cloud9 - 730 features accommodation with seating area. 2.7 km from United Center and 2.9 km from Chicago Museum of Contemporary Art, the property provides a garden and a terrace. Featuring a private bathroom with a shower and a hair dryer, units at the apartment complex also feature free WiFi, while selected rooms also boast a balcony. All units at the apartment complex have air conditioning and a wardrobe. Private parking can be arranged at an extra charge. Shops at Northbridge is 3 km from the apartment, while 360 Chicago is 3.1 km from the property. The nearest airport is Midway International Airport, 18 km from Presidential Penthouses w the best View- Cloud9 - 730.Show full description
Holiday Home.Newly opened, April 2024. Featuring air-conditioned accommodation with a patio, Stunning 2 Floor Penthouse Downtown is located in Chicago. Both free WiFi and parking on-site are available at the holiday home free of charge. United Center is 3.1 km from Stunning 2 Floor Penthouse Downtown, while Chicago Museum of Contemporary Art is 3.3 km away. The property is non-smoking and is set 3.1 km from Water Tower Chicago. The spacious holiday home comes with 3 bedrooms, a TV and a fully equipped kitchen that provides guests with a dishwasher, an oven, a washing machine, a microwave and a fridge. Towels and bed linen are provided in the holiday home. For added privacy, the accommodation features a private entrance. The nearest airport is Midway International Airport, 17 km from the accommodation.Show full description
Holiday Home.Newly opened, April 2024. Boasting air-conditioned accommodation with a patio, Stunning Condo #2 - Downtown River North is situated in Chicago. Both free WiFi and parking on-site are accessible at the holiday home free of charge. Popular points of interest near Stunning Condo #2 - Downtown River North include Water Tower Chicago, Chicago Museum of Contemporary Art and 360 Chicago. The property is non-smoking and is located 1.9 km from Oak Street Beach. The spacious holiday home has 3 bedrooms, a TV with cable channels and a fully equipped kitchen that provides guests with a dishwasher, an oven, a washing machine, a microwave and a fridge. Towels and bed linen are offered in the holiday home. For added privacy, the accommodation features a private entrance. The nearest airport is Midway International Airport, 19 km from the accommodation.Show full description
Apartment. Located in the centre of Chicago, less than 1 km from Oak Street Beach and a 17-minute walk from Ohio Street Beach, Charming 1BR Unit Great Location - Chestnut 19H offers free WiFi and air conditioning. The property is around less than 1 km from Shops at Northbridge, 1.8 km from Millennium Station and 2.1 km from CIBC Theatre. The spacious apartment features 1 bedroom, a flat-screen TV, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 1 bathroom with a shower. Towels and bed linen are featured in the apartment. The property is non-smoking and is situated 2.1 km from North Avenue Beach. At the apartment, there is a dressing room for guests to change in. Popular points of interest near Charming 1BR Unit Great Location - Chestnut 19H include Water Tower Chicago, Chicago Museum of Contemporary Art and 360 Chicago. The nearest airport is Midway International Airport, 19 km from the accommodation.Show full description
Apartment. Situated in Chicago, 3.2 km from Water Tower Chicago and 3.5 km from Union Station, Elegant Chicago Retreat with Spacious Balcony! offers air conditioning. The property is around 3.5 km from Chicago Museum of Contemporary Art, 3.7 km from 360 Chicago and 3.9 km from Shops at Northbridge. The spacious apartment includes 1 bedroom, a fully equipped kitchen with a dishwasher and an oven, as well as a coffee machine. Towels and bed linen are available in the apartment. Free WiFi is available throughout the property and United Center is 2.8 km away. For added privacy, the accommodation features a private entrance. Willis Tower is 4.1 km from the apartment, while CIBC Theatre is 4.2 km from the property. The nearest airport is Midway International Airport, 16 km from Elegant Chicago Retreat with Spacious Balcony!.Show full description
Apartment. Fully Furnished Apt Near Millenium Park- 29 features accommodation within less than 1 km of the centre of Chicago, with free WiFi, and a kitchen with a dishwasher, an oven and a microwave. 2.7 km from Ohio Street Beach and 400 metres from CIBC Theatre, the property offers a seasonal outdoor swimming pool and a garden. At the apartment complex, each unit includes a wardrobe, a flat-screen TV, a private bathroom, bed linen and towels. Popular points of interest near the apartment include Willis Tower, DePaul University and Chicago Symphony Orchestra. Private parking can be arranged at an extra charge. All units are air conditioned and include a seating and/or dining area. All units will provide guests with a fridge. The nearest airport is Midway International Airport, 17 km from Fully Furnished Apt Near Millenium Park- 29.Show full description
Apartment.Newly opened, March 2024. Elegant Chicago Studio Apartment - Dorchester 511 is located in the Hyde Park district of Chicago, 2.9 km from Oakwood Beach, 3 km from 63rd Street Beach and 1.8 km from Museum of Science and Industry - Chicago. The property is around 6.8 km from Guaranteed Rate Field, 8.8 km from Field Museum of Natural History and 10 km from Adler Planetarium & Astronomy Museum. The air-conditioned apartment is composed of 1 separate bedroom, a fully equipped kitchen with an oven and a microwave, and 1 bathroom. Towels and bed linen are featured in the apartment. The property is non-smoking and is set 2 km from 57th Street Beach. Buckingham Memorial Fountain is 11 km from the apartment, while DePaul University is 11 km away. The nearest airport is Midway International Airport, 13 km from Elegant Chicago Studio Apartment - Dorchester 511.Show full description
We do our best to keep this list very up to date. It was last edited in March 2024. If you know of a unique hotel that should be on the list, let us know. Click here to contact us. Thanks!
Check out these other cool hotel lists for Chicago: