Search all holiday resorts in Chicago, IL

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Chicago, IL resorts
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136 Best resorts in Chicago, IL

Best Chicago, IL resorts with a jacuzzi

Among the 136 accommodations in Chicago, IL, here are the 1 best resorts with a jacuzzi

Level - Deluxe Studio Fulton Market - Chicago, IL
10 2 reviews

Level - Deluxe Studio Fulton Market

resort, Chicago
This West Loop studio, one, two, or three-bedroom apartment is situated in Chicago's Fulton Market district, offering convenient access to the city's many attractions.
The luxury flat boasts a fully equipped gourmet kitchen, in-suite laundry, high-speed Wi-Fi, a private balcony with city views, and access to a fitness centre with a Peloton® room, a heated pool, and a hot tub; it sleeps up to two guests.

Best Chicago, IL resorts with a pool

Among the 136 accommodations in Chicago, IL, here are the 4 best resorts with a pool

Level Chicago - River North - Chicago, IL
9.2 2147 reviews

Level Chicago - River North

hotel, Chicago
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.
Level Chicago - Old Town - Chicago, IL
9.3 1130 reviews

Level Chicago - Old Town

hotel, Chicago
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.
Level - Deluxe Studio Fulton Market - Chicago, IL
10 2 reviews

Level - Deluxe Studio Fulton Market

resort, Chicago
This West Loop studio, one, two, or three-bedroom apartment is situated in Chicago's Fulton Market district, offering convenient access to the city's many attractions.
The luxury flat boasts a fully equipped gourmet kitchen, in-suite laundry, high-speed Wi-Fi, a private balcony with city views, and access to a fitness centre with a Peloton® room, a heated pool, and a hot tub; it sleeps up to two guests.
The Hotel & Athletic Club At Midtown - Chicago, IL
8.9 1369 reviews

The Hotel & Athletic Club At Midtown

resort, Chicago
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.

Frequently asked questions about resorts in Chicago, IL

  • What are the top attractions in Chicago, IL?

    You can't miss the iconic Willis Tower, formerly known as the Sears Tower, for stunning city views. The Art Institute of Chicago is a must for art lovers, boasting masterpieces like Edward Hopper's 'Nighthawks'. And of course, you'll want to take a stroll along Navy Pier, with its Ferris wheel, shops, and restaurants.
  • Which area in Chicago, IL is good for staying in a resort?

    Chicago doesn't really have resorts in the traditional sense. You'll find more luxury hotels in the Gold Coast or Streeterville, which are close to the Magnificent Mile and offer great views of Lake Michigan.
  • What time of the year is the best to stay in a resort Chicago, IL?

    Chicago is a great city to visit year-round, but if you're looking for warm weather and outdoor activities, the best time to visit would be during the summer months, from June to August. You'll have plenty of sunshine and opportunities to enjoy the city's parks and beaches.
  • How easy is it to get to Chicago, IL?

    Chicago is a major hub, so getting there is easy. O'Hare International Airport (ORD) is a major international airport with flights from all over the world. You can also get to Chicago by train, with Amtrak services running from many cities across the United States.
  • Where are the best markets in Chicago, IL?

    For a vibrant, local experience, head to the Maxwell Street Market on Sundays. It's a lively mix of food stalls, clothing vendors, and antiques. If you're looking for fresh produce, the Green City Market in Lincoln Park is a great option, running from May to October.
  • What are the best sports events or competitions happening in and around Chicago, IL?

    Chicago is a big sports city! You can catch a Chicago Cubs baseball game at Wrigley Field, or a Chicago White Sox game at Guaranteed Rate Field. If basketball is your thing, the Chicago Bulls play at the United Center.
  • What are the most requested amenities in resorts in Chicago, IL?

    While Chicago doesn't have many resorts, luxury hotels in the city often offer amenities like swimming pools, fitness centres, spas, and restaurants. You can also find rooftop bars and lounges with stunning views.
  • What are the most romantic attractions in Chicago, IL's?

    For a romantic evening, take a stroll along the Riverwalk and enjoy the city lights. You can also take a boat tour on Lake Michigan or have a picnic in Millennium Park, where you can admire Cloud Gate, the iconic bean sculpture.

Popular destinations

Best Chicago, IL resorts with air conditioning

The Golden Arm - Chicago, IL
8.8 1715 reviews

The Golden Arm

hotel, Chicago
The Ruby Room hotel is located in Chicago, around 3 kilometres west of the United Center and within 5 kilometres of several popular attractions, including Water Tower Chicago, Union Station, and the Chicago Museum of Contemporary Art. It offers a peaceful setting away from the hustle and bustle of the city centre, while still being within easy reach of major attractions and public transport. The hotel consistently receives very good user ratings, with excellent scores for location and cleanliness.
Rooms at the Ruby Room are comfortable and feature desks, private bathrooms with showers and free toiletries, and free Wi-Fi. Some rooms have balconies for enjoying fresh air and views. Guests can also enjoy a garden, a spa, and a concierge service. Parking is available, and the hotel has convenient access to public transport.

Best Chicago, IL resorts with a gym

Level Chicago - Old Town - Chicago, IL
9.3 1130 reviews

Level Chicago - Old Town

hotel, Chicago
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 Neighborhood Hotel - Lincoln Park Lp - Chicago, IL
9.5 989 reviews

The Neighborhood Hotel - Lincoln Park Lp

hotel, Chicago
This apartment is located in the popular Lincoln Park neighbourhood, just a short walk from Fullerton Beach, North Avenue Beach, and Lincoln Park Zoo. It has received excellent ratings for its location, cleanliness and user experience.
The apartment is comfortable and modern, with a fully equipped kitchen and a private bathroom. It offers a range of amenities including free Wi-Fi, air conditioning, and a terrace, making it an ideal choice for travellers looking to explore Chicago.
Level Chicago - River North - Chicago, IL
9.2 2147 reviews

Level Chicago - River North

hotel, Chicago
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.
Downtown Guild #3 | Mag Mile Gold Coast The Lake! - Chicago, IL
9.7 816 reviews

Downtown Guild #3 | Mag Mile Gold Coast The Lake!

resort, Chicago
This apartment is situated in a quiet part of Chicago, just a short walk from the lakefront, Magnificent Mile and John Hancock building. The accommodation has excellent user, location and cleanliness ratings.
The flat has two king-size beds, a queen-size sofa bed and a full dining room. Amenities include a fully equipped kitchen, a 50-inch smart TV, a gym, laundry facilities and a rooftop terrace.
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