Title: Hillside Vacation Packages & Trips 2026 from CA $718 | 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)

![](https://images.trvl-media.com/place/8353/de77b2af-26b0-4678-8e9f-d4750da04bfb.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Hillside Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

Photo by Joe Farmer

- ##  
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Save up to CA $1,096 when you book a flight and hotel together\*
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#### Your Hillside Vacation

An easy way to experience this vibrant city is with a custom-made Hillside vacation package. Base yourself in the neighborhood of Wicker Park, which is great for nightlife, bars and pubs and cafes or go someplace else — our packages are all about you. Any trip to Hillside needs a well-planned itinerary. Fill yours with major attractions such as [Brookfield Zoo](https://www.expedia.ca/Brookfield-Zoo-Chicago.d6064025.Vacation-Attraction), [Oakbrook Center Mall](https://www.expedia.ca/Oakbrook-Center-Mall-Chicago.d6186894.Vacation-Attraction) and [Yorktown Shopping Center](https://www.expedia.ca/Yorktown-Shopping-Center-Chicago.d6227539.Vacation-Attraction). Expedia can help you escape the everyday. Tailor your vacation to Hillside to suit your style of travel, whatever that may be.

## Top Hillside Vacation Deals

Price found within the past 48 hours. Click for updated prices.

![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Level Chicago – Old Town

Downtown Chicago

CA $718

per person

Mar 12 - Mar 15

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (380 reviews)

Staff was friendly did amazing job with checking us in

Reviewed on Dec 25, 2025

![La Banque Hotel](https://images.trvl-media.com/lodging/15000000/14710000/14702200/14702161/a8c9af9e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### La Banque Hotel

CA $891

per person

Mar 24 - Mar 29

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (447 reviews)

The room was spotless and the staff was good. Loved the hotel. Was just an overnight stay. Wish we had stayed another day. Loved the area.

Reviewed on Nov 30, 2025

![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Riu Plaza Chicago

Downtown Chicago

CA $768

per person

Mar 24 - Mar 29

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (2,790 reviews)

Rooms were clean, staff was super friendly. Kind of wish there was a spa or gym but free breakfast was a nice touch. You cant beat the location.

Reviewed on Dec 28, 2025

![Hilton Grand Vacations Club Chicago Magnificent Mile](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/843f6e73_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hilton Grand Vacations Club Chicago Magnificent Mile

Downtown Chicago

CA $1,048

per person

Mar 15 - Mar 21

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Chicago (ORD)

9.2/10 Wonderful! (317 reviews)

Room was very spacious and clean. The location was perfect walking distance from a lot great eating and tourists spots.

Reviewed on Dec 18, 2025

![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,017

per person

Mar 12 - Mar 15

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

Everything was perfect

Reviewed on Dec 29, 2025

## Ready to book your vacation to Hillside?

Choose your dates

## Hillside Hotel Deals

![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl Chicago IL

Fully refundableReserve now, pay when you stay

CA $122

CA $143 total

Jan 6 - Jan 7, 2026

includes taxes & fees

8.8/10 Excellent! (3,609 reviews)

Spotless room, very nice staff

Reviewed on Dec 29, 2025

[](https://expedia.ca/Hotel-Search?startDate=06%2F01%2F2026&endDate=07%2F01%2F2026&selected=18514&PinnedHotelID=18514&HadPinnedHotel=true&regionId=8353)

![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Palmer House a Hilton Hotel

17 E Monroe St Chicago IL

Fully refundableReserve now, pay when you stay

CA $180

CA $245 total

Jan 5 - Jan 6, 2026

includes taxes & fees

8.4/10 Very Good! (2,175 reviews)

Great place

Reviewed on Dec 26, 2025

[](https://expedia.ca/Hotel-Search?startDate=05%2F01%2F2026&endDate=06%2F01%2F2026&selected=8079&PinnedHotelID=8079&HadPinnedHotel=true&regionId=8353)

![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hilton Chicago

720 S Michigan Ave Chicago IL

Fully refundableReserve now, pay when you stay

CA $167

CA $236 total

Jan 6 - Jan 7, 2026

includes taxes & fees

8.4/10 Very Good! (2,417 reviews)

Check in staff were great and room was clean. Worst part was house cleaner knocking at door at 1030am, after being up till 2am night before have a good time at football game. Hot tub amazing and our view!

Reviewed on Dec 27, 2025

[](https://expedia.ca/Hotel-Search?startDate=06%2F01%2F2026&endDate=07%2F01%2F2026&selected=12570&PinnedHotelID=12570&HadPinnedHotel=true&regionId=8353)

[See all 5,219 properties in Hillside](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=31%2F12%2F2025&endDate=01%2F01%2F2026&regionId=8353)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

### Discover the most popular places to visit in Hillside

![Magnificent Mile - River North which includes signage, a city and night scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/23000/23728-Magnificent-Mile.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Michigan Avenue

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants. 

[](https://expedia.ca/Michigan-Avenue-Downtown-Chicago.d6156167.Vacation-Attraction)

![Wrigley Field featuring central business district, a city and a sporting event](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/35000/35620-Wrigley-Field.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

[](https://expedia.ca/Wrigley-Field-Lakeview.d6034754.Vacation-Attraction)

![Navy Pier](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/54000/54738-Navy-Pier-Chicago.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

[](https://expedia.ca/Navy-Pier-Downtown-Chicago.d6069215.Vacation-Attraction)

### What to do in Hillside

![Color Factory Chicago Ticket](https://mediaim.expedia.com/localexpert/49191714/feac7bb1-c7ea-4b19-8342-818eafa34e83.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Color Factory Chicago Ticket

CA $47

per adult

**96%** of travellers recommend

[](https://expedia.ca/things-to-do/color-factory-chicago-ticket.a49191714.activity-details)

![Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting](https://mediaim.expedia.com/localexpert/4973725/0b36f3b1-b375-4fa2-8cfd-1a9815dcdcdc.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting

CA $44

per adult

**96%** of travellers recommend

[](https://expedia.ca/things-to-do/medieval-torture-museum-ticket-with-audio-guide-and-ghost-hunting.a4973725.activity-details)

![Chicago's Navy Pier Centennial Wheel Ticket](https://mediaim.expedia.com/localexpert/48840807/49f0c7f9-d7f7-4281-a580-006a5c5fd53f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Chicago's Navy Pier Centennial Wheel Ticket

CA $33

per adult

**100%** of travellers recommend

[](https://expedia.ca/things-to-do/chicagos-navy-pier-centennial-wheel-ticket.a48840807.activity-details)

[See all activities in Hillside](https://expedia.ca/things-to-do/search?rid=8353)

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- [Legoland® Discovery Center ](https://www.expedia.ca/LEGOLAND-Discovery-Center-Chicago.d6169680.Vacation-Attraction)
- [Lakeview Vacations ](https://www.expedia.ca/Lakeview.d178166.Destination-Travel-Guides)
- [Loretto Hospital ](https://www.expedia.ca/Loretto-Hospital-Austin.d553248635997986962.Vacation-Attraction)
- [Melrose Park Vacations ](https://www.expedia.ca/Melrose-Park.d8800.Destination-Travel-Guides)
- [Monument Park ](https://www.expedia.ca/Monument-Park-Edison-Park.d553248635015525139.Vacation-Attraction)
- [Morton Arboretum ](https://www.expedia.ca/Morton-Arboretum-Chicago.d6238155.Vacation-Attraction)
- [Norma Vacations ](https://www.expedia.ca/Norma.d6132336.Destination-Travel-Guides)
- [River Forest Vacations ](https://www.expedia.ca/River-Forest.d5986.Destination-Travel-Guides)
- [Rosemont Vacations ](https://www.expedia.ca/Rosemont.d7581.Destination-Travel-Guides)
- [Sleepy Hollow Vacations ](https://www.expedia.ca/Sleepy-Hollow.d6132427.Destination-Travel-Guides)
- [United Center ](https://www.expedia.ca/United-Center-Near-West-Side.d6064077.Vacation-Attraction)
- [Unity Temple ](https://www.expedia.ca/Unity-Temple-Chicago.d6064079.Vacation-Attraction)
- [Wheaton Vacations ](https://www.expedia.ca/Wheaton.d7599.Destination-Travel-Guides)
- [Woodfield Mall ](https://www.expedia.ca/Woodfield-Mall-Chicago.d6064089.Vacation-Attraction)
- [Wrigley Field ](https://www.expedia.ca/Wrigley-Field-Lakeview.d6034754.Vacation-Attraction)
- [Yorktown Shopping Center ](https://www.expedia.ca/Yorktown-Shopping-Center-Chicago.d6227539.Vacation-Attraction)

- [Westchester Vacation Rentals ](https://www.expedia.ca/Westchester-Vacation-Rentals.d7758.Travel-Guide-VacationRentals)

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

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