Search all holiday resorts in Chicago, IL

Located in Chicago, the Level – A City Escape. Junior Two Bedroom Suite offers a sophisticated urban living experience with convenient access to city views, situated just outside the busiest downtown core.
This spacious 76 square meter suite accommodates up to four guests and features two spa-inspired bathrooms, a fully-equipped gourmet kitchen, and access to over 2,787 square meters of indoor and outdoor amenities including a seasonal heated pool, hot tub, fitness centre, steam room, dry sauna, media room, grill stations, and a bocce court.

Level Chicago - River North, situated in Chicago's River North district, is 2.3 kilometres from Ohio Street Beach and near the Shops at Northbridge.
This hotel boasts a seasonal outdoor pool, fitness centre, sauna, hot tub, barbecue facilities, free Wi-Fi, and private parking, offering guests a range of amenities.

This Chicago Loop apartment offers a prime location, within easy walking distance of the Theatre District, River North, Millennium Park, and the Magnificent Mile.
The one-bedroom flat sleeps three, includes in-unit laundry, a contemporary kitchen, high-speed internet, and access to a rooftop swimming pool, jacuzzi, and fitness centre; enjoy nearby activities such as exploring the Art Institute of Chicago or catching a show in the Theatre District.

This luxury hotel, offering the "Level- Beautiful Two Bedroom Junior Suite", is located in a prime Chicago district, providing easy access to downtown attractions.
This accommodation boasts sophisticated suites with modern design, floor-to-ceiling windows offering city views, a fully-equipped gourmet kitchen, private balconies, and over 3,000 square metres of indoor and outdoor amenities including an outdoor heated pool, hot tub, and a state-of-the-art fitness centre with a Peloton room.

This three-bedroom, two-bathroom penthouse apartment in Chicago's Loop district is situated two blocks from Grant Park and the lakefront, offering immediate access to the Red Line and many attractions.
The 28th-floor dwelling boasts a private rooftop deck, city views, two king-size and one queen-size bed, accommodating up to eight guests, and includes access to a fitness centre, swimming pool, and secure parking.

The "Amazing 1br 1ba Great Location Awesome Views +Pool" is a one-bedroom apartment located in Chicago's West Loop, a district known for its restaurants and nightlife, offering immediate access to these amenities.
This aparthotel provides accommodation for two guests, featuring a modern kitchen, in-unit laundry, a shared outdoor kitchen, a fitness centre, and a swimming pool, with a minimum stay of 32 days suitable for extended visits.

Level Chicago - Old Town is situated in the trendy Old Town neighbourhood, a short walk from Oak Street and North Avenue beaches and known for its historic architecture and lively nightlife. The hotel has excellent user, location, and cleanliness ratings, making it a popular choice for travellers.
The hotel offers a range of accommodation options, including rooms with balconies. Guests have access to a swimming pool, fitness centre, spa, sauna, hot tub, shared kitchen, terrace, lounge, ping pong and darts, a business centre, and a restaurant.

The Hotel & Athletic Club at Midtown is conveniently located in Chicago's Midtown neighbourhood, just a short distance from popular attractions like Wrigley Field, Lincoln Park Zoo, and United Center. The hotel consistently receives high ratings for its cleanliness, location, and overall experience, making it a popular choice for travellers.
The hotel offers a range of comfortable and modern rooms, each equipped with amenities such as air conditioning, flat-screen TVs, and private bathrooms. Guests have access to a wide array of facilities including indoor and outdoor swimming pools, a spa, a fitness centre, tennis courts, and a variety of fitness classes, making it a great choice for those seeking a wellness-focused getaway.

The "Level-stunning One Bedroom Suite In River North" is a sophisticated serviced apartment situated in Chicago's River North district, offering impressive city views and easy access to downtown attractions.
This pet-friendly accommodation for up to four guests features a fully-equipped gourmet kitchen, a private balcony, and access to amenities including an outdoor heated pool, hot tub, and a state-of-the-art fitness centre with a Peloton room.

This one-bedroom suite, the "Level River North - Chic One Bedroom Suite," is situated in Chicago's River North district, offering a modern sanctuary with city views.
This accommodation for four guests boasts a private balcony, a fully-equipped gourmet kitchen, an outdoor heated pool, a hot tub, a state-of-the-art fitness centre with a Peloton room, and 24/7 concierge services.

"The Marlowe" A Couples Getaway offers a private, one-bedroom lodging for two in Chicago, featuring a luxurious six-person hot tub, an 80-inch smart TV with surround sound, a private rear deck with a barbecue, and a pool table, all situated on the exclusive first floor for ultimate privacy. This secluded retreat provides a spa-like experience with Bluetooth ceiling speakers and optional hibachi grill and chef services available at an additional cost.

This one-bedroom Chicago apartment, located near Hotel Nemo in a trendy neighbourhood close to award-winning restaurants and fashionable shops, offers a convenient base for exploring the city.
The 1-bathroom flat sleeps two guests and includes amenities such as a fully equipped kitchen with fridge, in-unit washer/dryer, high-speed Wi-Fi, a Keurig coffee maker, and access to premium food delivery services; garage parking is available for an additional £140 per month.

This modern one-bedroom apartment, offering a minimum 32-night stay under the "Modern 1br In Full-amenity Building! 32 Night Min" offer, is located a mere 200 metres from Chicago's Loop and River North districts.
This comfortable flat accommodates up to three guests and features in-unit laundry, high-speed internet, a contemporary kitchen, and access to building amenities including an indoor swimming pool and fitness centre.

This executive one-bedroom suite is located in Chicago's River North district, offering convenient access to the city's attractions.
The suite features a fully-equipped kitchen, open-air balcony, a seasonal outdoor heated pool, hot tub, and a state-of-the-art fitness centre with a dedicated Peloton® room, accommodating up to two guests.

The Level- A Dream Extended Stay One Bedroom Suite is situated in Chicago's River North district, offering convenient access to city landmarks, with the Magnificent Mile approximately 800 meters away.
This pet-friendly luxury suite accommodates up to four guests, featuring a private balcony with city views, a fully-equipped gourmet kitchen, an outdoor heated pool, a hot tub, and a state-of-the-art fitness centre, all with GBAC STAR™ facility accreditation.