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 table with wine bottles, glasses, and a decorative vase with flowers.
A bathroom with a white bathtub, a towel rack with towels, a door, and a patterned wall.
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 downtown access.
₩608,696
₩735,851 total
includes taxes & fees
Oct 14 - Oct 15
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

Top Chicago Hotel Reviews

Frequently asked questions

Looking for Chicago all-inclusive resorts?
Chicago is known for shopping and culture, and offers a host of things to see and do such as Navy Pier and CIBC Theatre. Browse our choice of all-inclusive hotel rooms where you can enjoy a host of amenities including entertainment, kid's clubs, and of course food and beverages all included in your stay. Many of our all-inclusive resorts also feature activities such as golf, yoga, water sports, and more, which you can enjoy without any 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 travelers 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 vacation in Chicago to revive you, especially when you know what to expect from the elements. Here's some info to help you decide when to book: The hottest months are usually July and August with an average temp of 70°F, while the coldest months are January and February with an average of 31°F. 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, making the most of your time in Chicago is a breeze. You can walk to nearby metro stations including 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) away. If you'd like to explore around the area, consider renting a car to take in more sights.

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