Title: Book the Best Hillside, IL ALL INCLUSIVE Resorts and Hotels | Expedia.ca

[Hotels in Hillside](https://expedia.ca/Hillside-Hotels.d8353.Travel-Guide-Hotels)[Vacation Rentals in Hillside](https://expedia.ca/Hillside-Vacation-Rentals.d8353.Travel-Guide-VacationRentals)[Flights to Hillside](https://expedia.ca/Cheap-Flights-To-Hillside.d8353.Travel-Guide-Flights)[Hillside Car Rentals](https://expedia.ca/Car-Rentals-In-Hillside.d8353.Car-Rental-Guide)[Hillside Vacation Packages](https://expedia.ca/Hillside.d8353.Destination-Travel-Guides)

![If you're in Chicago and like to visit famous grave sites, here is one not to miss. ](https://images.trvl-media.com/place/8353/04417658-847c-4a59-a291-8bfe14a93297.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Off The Beaten Track

![](https://images.trvl-media.com/place/8353/04417658-847c-4a59-a291-8bfe14a93297.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check availability on Hillside All Inclusive Resorts and Hotels

Tonight

[Feb 1 - Feb 2](https://www.expedia.ca/Hotel-Search?regionId=8353&startDate=2026-02-01&endDate=2026-02-02&adults=2&amenities=ALL_INCLUSIVE&mealPlan=ALL_INCLUSIVE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Feb 2 - Feb 3](https://www.expedia.ca/Hotel-Search?regionId=8353&startDate=2026-02-02&endDate=2026-02-03&adults=2&amenities=ALL_INCLUSIVE&mealPlan=ALL_INCLUSIVE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=8353&startDate=2026-02-06&endDate=2026-02-08&adults=2&amenities=ALL_INCLUSIVE&mealPlan=ALL_INCLUSIVE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=8353&startDate=2026-02-13&endDate=2026-02-15&adults=2&amenities=ALL_INCLUSIVE&mealPlan=ALL_INCLUSIVE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Hillside all-inclusive hotels

![Signature Suite, 1 Bedroom](https://images.trvl-media.com/lodging/8000000/7820000/7818200/7818107/896f58e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/8000000/7820000/7818200/7818107/18dd5e87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Signature Suite, 1 Bedroom](https://images.trvl-media.com/lodging/8000000/7820000/7818200/7818107/d8db67da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Suite](https://images.trvl-media.com/lodging/8000000/7820000/7818200/7818107/bf7253c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Wheeler Mansion

[](https://www.expedia.ca/Chicago-Hotels-The-Wheeler-Mansion.h7818107.Hotel-Information)

Near South Side

9.0/10

Wonderful

(4 reviews)

"A unique place to stay near the convention centre. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Leonardo

[](https://www.expedia.ca/Chicago-Hotels-The-Wheeler-Mansion.h7818107.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-02-15&endDate=2026-02-16&regionId=8353&adults=2&mealPlan=ALL_INCLUSIVE&sort=RECOMMENDED&openPlayBack=true)

## Top Hillside Hotel Reviews

## Frequently asked questions

### How much does an all-inclusive hotel in Hillside cost?

### What area of Hillside is best for all-inclusive hotels?

> For families, the hotels in this area are designed with comfort and convenience in mind. Spacious rooms, kid-friendly activities, and easy access to attractions make it an ideal choice. Parents can enjoy peace of mind knowing that everything they need is within reach, allowing for a stress-free holiday.
> 
>   
> Couples seeking a romantic escape can also find suitable options here. Many all-inclusive hotels offer special packages that include spa services, fine dining, and intimate settings, superb for unwinding together after a day of exploring.

### What is the best time to stay at an all-inclusive hotel in Hillside?

> Summer in Hillside is lively, with plenty of activities for families and couples alike. You can expect a range of events, from local festivals to outdoor concerts, all of which create an engaging atmosphere for visitors. The warm weather encourages guests to take advantage of the hotel amenities, whether it's lounging by the pool or participating in organized outdoor games.
> 
>   
> If you're looking for a more budget-friendly option with a more relaxed vibe, consider visiting in September. The weather remains warm, generally between 20°C and 25°C, but the crowds have thinned out since the peak summer season. This can lead to better rates on accommodations and a more local feel, allowing you to enjoy the area without the hustle and bustle of peak tourist traffic.

### How can I save on an all-inclusive hotel in Hillside with Expedia?

### Is it cheaper to book an all-inclusive hotel and flight package in Hillside?

### What all-inclusive amenities should we expect at hotels in Hillside?

### Can I cancel my all-inclusive hotel reservation on Expedia?

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