A river with a yellow boat, surrounded by tall buildings and a bridge.

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Our top choices for Chicago all-inclusive hotels

A formal dining room with a long table set for a meal, surrounded by chairs, and decorated with potted plants.
A well-maintained lawn with croquet hoops and balls, surrounded by lush greenery and trees.
A table with wine bottles, glasses, and a decorative vase with flowers.
A historic building with a prominent American flag, a flag with a crest, and a grand entrance with steps and columns.

1. The Wheeler Mansion

The Wheeler Mansion
Near South Side
  • Tropical paradise meets luxury in this all-inclusive mansion with gourmet meals, gardens, and city centre access.
฿14,875
฿17,983 total
includes taxes & fees
14 Oct - 15 Oct
The Wheeler Mansion
View all properties

Choose what matters most at all-inclusive hotels in Chicago

Adult-only
5 stars
4 stars
Pool
Water park

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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 Navy Pier 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 Navy Pier and CIBC Theatre, and see why travellers like the shopping and cultural scene in Chicago. Other top attractions include Millennium Park, Soldier Field 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.

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