Chicago Hotel Guide - All Inclusive Hotels in Chicago, Illinois

    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
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Chicago All Inclusive Hotels

Top Chicago All Inclusive Hotels

Eaglewood Resort and Spa

4.0 star property
8.6 out of 10, Excellent, (1027)
"The room was clean and bed was comfortable."
The price is €122
includes taxes & fees
27 Jul - 28 Jul
Eaglewood Resort and Spa

Hilton Chicago/Oak Brook Hills Resort & Conference Center

4.0 star property
8.6 out of 10, Excellent, (1002)
"Will stay here again! "
The price is €139
includes taxes & fees
27 Jul - 28 Jul
Hilton Chicago/Oak Brook Hills Resort & Conference Center

citizenM Chicago Downtown

4.0 star property
9.4 out of 10, Exceptional, (3390)
"Great location- fun hotel"
The price is €167
includes taxes & fees
17 Aug - 18 Aug
citizenM Chicago Downtown

Lincolnshire Marriott Resort

4.0 star property
8.8 out of 10, Excellent, (977)
"We had a great stay! The staff and food were wonderful! "
The price is €125
includes taxes & fees
16 Aug - 17 Aug
Lincolnshire Marriott Resort

Ivy Boutique Hotel

4.5 star property
8.8 out of 10, Excellent, (1004)
"Front desk was very welcoming and hotel was beautiful"
The price is €160
includes taxes & fees
27 Jul - 28 Jul
Ivy Boutique Hotel

The Westin Chicago Lombard

4.0 star property
8.8 out of 10, Excellent, (1002)
"Great stay - Staff was very helpful and friendly!"
The price is €129
includes taxes & fees
27 Jul - 28 Jul
The Westin Chicago Lombard

Hampton Inn & Suites Chicago Waukegan

2.5 star property
9.0 out of 10, Wonderful, (1002)
"Great guest service."
The price is €106
includes taxes & fees
17 Aug - 18 Aug
Hampton Inn & Suites Chicago Waukegan

Hampton Inn Chicago Downtown/N Loop/Michigan Ave

3.0 star property
8.2 out of 10, Very good, (1003)
"Excellent location with parking. Nice staff! "
The price is €164
includes taxes & fees
10 Aug - 11 Aug
Hampton Inn Chicago Downtown/N Loop/Michigan Ave

The Emily Hotel

4.0 star property
9.2 out of 10, Wonderful, (1132)
"Great hotel, location, friendly staff, and overall fit the bill very well!"
The price is €537
includes taxes & fees
1 Aug - 2 Aug
The Emily Hotel

Hotel Saint Clair- Magnificent Mile

4.0 star property
8.2 out of 10, Very good, (1666)
"I really enjoyed my stay here, the staff was very pleasant and the rooms great!"
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.