All Inclusive Hotels and Resorts in Chicago

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Chicago All Inclusive Hotels and Resorts

Top All Inclusive Hotels and Resorts in Chicago

Eaglewood Resort and Spa
Front of property – evening/night

Eaglewood Resort and Spa

4.0 star property
8.6 out of 10, Excellent, (1019)
"The king room was so spacious! Very clean and an amazing view of the golf course. "
Malak
The price is S$232
includes taxes & fees
20 Jul - 21 Jul
Eaglewood Resort and Spa
Hilton Chicago/Oak Brook Hills Resort & Conference Center
Front of property – evening/night

Hilton Chicago/Oak Brook Hills Resort & Conference Center

4.0 star property
8.6 out of 10, Excellent, (1012)
"The pool was great! My daughter and her friends had a blast. Staff was helpful, my request for connecting rooms was granted. Service at the restaurant was excellent. Unfortunately our room had a very strong chemical cleaner smell which was pretty awful. I would have changed rooms but the connecting room was fine and my daughter and friends had already settled in. "
Sally
The price is S$194
includes taxes & fees
10 Aug - 11 Aug
Hilton Chicago/Oak Brook Hills Resort & Conference Center
citizenM Chicago Downtown
Terrace/patio

citizenM Chicago Downtown

4.0 star property
9.4 out of 10, Exceptional, (3355)
"Great location, helpful staff and self service is very convenient. Great view of the city. "
Marquita
The price is S$248
includes taxes & fees
11 Aug - 12 Aug
citizenM Chicago Downtown
Lincolnshire Marriott Resort
Banquet hall

Lincolnshire Marriott Resort

4.0 star property
8.8 out of 10, Excellent, (971)
"This hotel is a comfortable and friendly place to stay. We have no complaints at all. What a nice area. Everything and everyone there was pleasant. Kudos to housekeeping! They all were wonderful!"
Robert P
The price is S$199
includes taxes & fees
25 Jul - 26 Jul
Lincolnshire Marriott Resort
Ivy Boutique Hotel
Front of property

Ivy Boutique Hotel

4.5 star property
8.8 out of 10, Excellent, (1016)
"The hotel is really clean, large rooms, nice bathrooms and showers, big soaking tub. Quite nice"
Joesph
The price is S$272
includes taxes & fees
4 Aug - 5 Aug
Ivy Boutique Hotel
The Westin Chicago Lombard
Exterior

The Westin Chicago Lombard

4.0 star property
8.8 out of 10, Excellent, (1004)
"Room was great and so was the view "
Tiana
The price is S$192
includes taxes & fees
27 Jul - 28 Jul
The Westin Chicago Lombard
Hampton Inn & Suites Chicago Waukegan
Terrace/patio

Hampton Inn & Suites Chicago Waukegan

2.5 star property
9.0 out of 10, Wonderful, (1002)
"The staff were very friendly & helpful. The bed was super comfortable - always had a peaceful night’s sleep. Delicious coffee & tea flowing all day & night, as well as a vast variety of
breakfast
choices each day. Despite being busy at times, it was always quiet inside the room. Great vibes here overall."
Lynette
The price is S$169
includes taxes & fees
20 Jul - 21 Jul
Hampton Inn & Suites Chicago Waukegan
Hampton Inn Chicago Downtown/N Loop/Michigan Ave
Exterior

Hampton Inn Chicago Downtown/N Loop/Michigan Ave

3.0 star property
8.2 out of 10, Very good, (1007)
"Very convenient. Nice comfortable room. Very good
breakfast
."
Ranjith
The price is S$267
includes taxes & fees
27 Jul - 28 Jul
Hampton Inn Chicago Downtown/N Loop/Michigan Ave
The Emily Hotel
Exterior

The Emily Hotel

4.0 star property
9.2 out of 10, Wonderful, (1126)
"Staying at The Emily was a great experience for my first trip to Chicago. The location is great, as it's close to so many attractions and
restaurants
, including a delicious on-site restaurant, Fora, which I had twice in my three days. The front desk staff was friendly and informative, while the cleaning staff left my room sparkling. The room offered plenty of natural light, a comfortable king bed and a strong air conditioner (which was a necessity during a heat wave). I will definitely be...
Michael
The price is S$475
includes taxes & fees
13 Aug - 14 Aug
The Emily Hotel
Hotel Saint Clair- Magnificent Mile
Restaurant

Hotel Saint Clair- Magnificent Mile

4.0 star property
8.2 out of 10, Very good, (1678)
"Beautiful hotel, wonderful and accommodating staff. Hotel is in a great location, easy access to
restaurants
, shopping, walking. "
Elaine
Hotel Saint Clair- Magnificent Mile
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Looking for Chicago all-inclusive resorts?
Chicago is known for its shopping and culture, and offers a host of things to see and do, such as Michigan Avenue and CIBC Theatre. Look through our choice of all-inclusive accommodation options, where you can enjoy a range of amenities such as entertainment, childrens' clubs and, of course, food and drinks, all included in your room rate. Many of our all-inclusive resorts also feature activities such as golf, yoga, water sports and more, which you can enjoy at no additional cost.
What is there to do near my all-inclusive resort in Chicago?
If you want to venture outside of your all-inclusive resort, head to Michigan Avenue and CIBC Theatre, and see why travellers like the shopping and cultural scene in Chicago. Other top attractions include Millennium Park, Navy Pier and McCormick Place.
When's the best time for an all-inclusive stay in Chicago?
There's nothing like an all-inclusive holiday in Chicago to revive you, especially when you know what to expect from the elements. Here's some information to help you decide when to book: The hottest months are usually July and August, with an average temperature of 21°C, while the coldest months are January and February, with an average of -1°C. November and January are the driest months, while June and May are the rainiest months.
What's the best way to get to Chicago and explore the area?
With plenty of transportation options, seeing Chicago is a breeze. Walk to nearby metro stations such as Monroe Station (Red Line), Monroe Station (Blue Line) and Adams-Wabash Station. The closest major airport is Chicago Midway Airport (MDW), which is located 8.6 mi (13.9 km) from the city centre. If you'd like to explore around the area, you may want to rent a car for your trip.