Title:  Hillside Vacation Packages & Trips 2025 from $366 | Expedia.ca

  

[Hillside Travel Guide](https://expedia.ca/Milwaukee-Hillside.dx870620351623675904)[Hotels in Hillside](https://expedia.ca/Hillside-Milwaukee-Hotels.0-n870620351623675904-0.Travel-Guide-Filter-Hotels)[Flights to Milwaukee](https://expedia.ca/Cheap-Flights-To-Milwaukee.d602647.Travel-Guide-Flights)[Things to do in Milwaukee](https://expedia.ca/Things-To-Do-In-Milwaukee.d602647.Travel-Guide-Activities)[Hillside Car Rentals](https://expedia.ca/Car-Rentals-In-Hillside.d870620351623675904.Car-Rental-Guide)

![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium)

# Hillside Vacation Packages

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

-   ## 
    
    Plan, book, travel with confidence
    

### 

Better together

Save up to CA $1,096 when you book a flight and hotel together\*

### 

Find the right fit

With over 300,000 hotels worldwide, it's easy to create a perfect package

### 

Rest easy

Plan, book, and manage your trip all in one place

## Top Holiday Package Deals in Hillside

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

![Kinn Guesthouse Bay View](https://images.trvl-media.com/lodging/21000000/20240000/20233300/20233264/4e3a3faa_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Kinn Guesthouse Bay View

Bay View

CA $949

per person

Dec 7 - Dec 11

found 22 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Milwaukee (MKE)

9.6/10 Exceptional! (410 reviews)

The house was spacious and well equipped the downstairs restaurant was great. The stairs up to the guest rooms were reminiscent of Europe where elevators are scarce

Reviewed on Sep 10, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-07/2025-12-11/?FromAirport=YUL&Destination=MKE&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20233264&paandie=true&dealMarker=KqymaQIWl1PipYfhsjshFyTNnOV25vb6NZf4b1nnq1XGMqSWzOB-29XBHHGLoPNr)

![Saint Kate - The Arts Hotel](https://images.trvl-media.com/lodging/1000000/30000/23300/23253/63d91083_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Saint Kate - The Arts Hotel

Downtown Milwaukee

CA $1,051

per person

Dec 7 - Dec 11

found 22 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Milwaukee (MKE)

9.8/10 Exceptional! (2,411 reviews)

What a great property! The staff was super friendly, helpful and accommodating. The Expedia VIP benefit was given up-front without me having to ask for it. The property itself was exceptionally well-kept. The location is amazing. Downtown Milwaukee is super walkable (in the right season, depending on your tolerance to cold weather) and this property is pretty much central to everything you could want! Will stay again. A+++

Reviewed on Sep 15, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-07/2025-12-11/?FromAirport=YUL&Destination=MKE&NumRoom=1&NumAdult=2&NumChild=0&hotelId=23253&paandie=true&dealMarker=KqymaQIWl1PipYfhsjshFxESPx7AK9Q8CbUobnc-2y2tB4RYxStmMaTt9RZSp3PK)

![Kinn Guesthouse Downtown](https://images.trvl-media.com/lodging/71000000/70260000/70257500/70257476/c20e864a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Kinn Guesthouse Downtown

Downtown Milwaukee

CA $1,018

per person

Dec 7 - Dec 11

found 22 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Milwaukee (MKE)

9.4/10 Exceptional! (292 reviews)

Would definitely stay here again!

Reviewed on Sep 6, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-07/2025-12-11/?FromAirport=YUL&Destination=MKE&NumRoom=1&NumAdult=2&NumChild=0&hotelId=70257476&paandie=true&dealMarker=KqymaQIWl1PipYfhsjshFxESPx7AK9Q8CbUobnc-2y3lAp_3lfb0WsFc1TAiT98c)

![Potawatomi Hotel & Casino](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474917/d47b7999_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Potawatomi Hotel & Casino

CA $1,016

per person

Dec 7 - Dec 11

found 22 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Milwaukee (MKE)

9/10 Wonderful! (1,362 reviews)

All was excellent- can’t wait to go back

Reviewed on Sep 18, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-07/2025-12-11/?FromAirport=YUL&Destination=MKE&NumRoom=1&NumAdult=2&NumChild=0&hotelId=8474917&paandie=true&dealMarker=KqymaQIWl1PipYfhsjshFxESPx7AK9Q8CbUobnc-2y0-tEqBpj0_LJViZ13acUbk)

![The Brewhouse Inn & Suites](https://images.trvl-media.com/lodging/8000000/7090000/7084400/7084340/c5b60965_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Brewhouse Inn & Suites

Westown

CA $974

per person

Dec 7 - Dec 11

found 22 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Milwaukee (MKE)

9.4/10 Exceptional! (1,025 reviews)

Love it best hotel I been in

Reviewed on Sep 15, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-07/2025-12-11/?FromAirport=YUL&Destination=MKE&NumRoom=1&NumAdult=2&NumChild=0&hotelId=7084340&paandie=true&dealMarker=KqymaQIWl1PipYfhsjshFyTNnOV25vb6NZf4b1nnq1UiK8195i7xAGTdlBEGaJrc)

## Where to stay in Hillside

Find the best Hillside areas and neighborhoods for the activities you enjoy most. [Learn more about Hillside](https://expedia.ca/Milwaukee-Hillside.dx870620351623675904)

![Milwaukee](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/219000/219557-Milwaukee.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Downtown Milwaukee

Central business district with cultural, financial, and historical landmarks, Downtown Milwaukee offers shopping at The Shops of Grand Avenue, art galleries in the Historic Third Ward, high-end dining, and vibrant nightlife. Explore the Milwaukee Public Market and Riverwalk, or hop on the free streetcar system.

[Find hotel + flight trips in Downtown Milwaukee](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Downtown%20Milwaukee&DestID=6059651&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Milwaukee County Zoo which includes zoo animals and dangerous animals as well as a family](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/31000/31457-Milwaukee-County-Zoo.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Wauwatosa

2 out of top 10 points of interest in this area

Wauwatosa is known for its abundant dining options, and you can plan a trip to Milwaukee County Zoo and Mayfair Mall while you're in town.

[Find hotel + flight trips in Wauwatosa](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Wauwatosa&DestID=6059657&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Milwaukee Art Museum](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/219000/219539-Milwaukee.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### East Town

4.5/5(18 area reviews)

East Town is highly notable for its fantastic nightlife, and you might want to visit top sights like Lake Michigan and Veteran's Park. See more of Milwaukee by jumping on the metro at Michigan & Jackson Tram Stop or Clybourn & Jefferson Tram Stop.

[Find hotel + flight trips in East Town](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=East%20Town&DestID=6338567&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Historic Third Ward](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/220000/220065-Historic-Third-Ward.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Historic Third Ward

5/5(1 area review)

Experience a historic warehouse district with a mix of specialty shops, art galleries, and restaurants. Visit the Milwaukee Institute of Art and Design, and enjoy year-round gourmet options at the Milwaukee Public Market, easily accessible via The Hop.

[Find hotel + flight trips in Historic Third Ward](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Historic%20Third%20Ward&DestID=6334279&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Milwaukee Public Library which includes interior views](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/31000/31500-Milwaukee-Public-Library.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Westown

1 out of top 10 points of interest in this area

4/5(8 area reviews)

While visiting Westown, you might make a stop by sights like Miller High Life Theatre and Milwaukee Public Museum.

[Find hotel + flight trips in Westown](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Westown&DestID=553248635976470851&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

## Hillside Hotel Deals

![The Pfister Hotel](https://images.trvl-media.com/lodging/1000000/20000/19500/19467/be11391f_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

The Pfister Hotel

424 E Wisconsin Ave, Milwaukee, WI

CA $246

CA $290 total

Sep 28 - Sep 29

includes taxes & fees

9.4/10 Exceptional! (1,738 reviews)

Pfister Hotel is Excellent

"The Pfister Hotel is excellent. Beautiful and very clean. Top notch service. Food is very good. They treat you as royalty. I will stay there again when back in Milwaukee"

Reviewed on Sep 15, 2025

[](https://expedia.ca/Hotel-Search?startDate=28%2F09%2F2025&endDate=29%2F09%2F2025&selected=19467&PinnedHotelID=19467&HadPinnedHotel=true&regionId=870620351623675904)

![Drury Plaza Hotel Milwaukee Downtown](https://images.trvl-media.com/lodging/33000000/32510000/32501800/32501737/ac1d9528_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Drury Plaza Hotel Milwaukee Downtown

700 N. Water Street, Milwaukee, WI

Fully refundableReserve now, pay when you stay

CA $176

CA $207 total

Sep 25 - Sep 26

includes taxes & fees

9.6/10 Exceptional! (1,898 reviews)

"Comfortable room, nice bed, great shower, conveniently located, loved the staff, breakfast and 5:30 Kickback were a terrific bonus!"

Reviewed on Sep 16, 2025

[](https://expedia.ca/Hotel-Search?startDate=25%2F09%2F2025&endDate=26%2F09%2F2025&selected=32501737&PinnedHotelID=32501737&HadPinnedHotel=true&regionId=870620351623675904)

![Potawatomi Hotel & Casino](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474917/d47b7999_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Potawatomi Hotel & Casino

1611 West Canal Street, Milwaukee, WI

Fully refundableReserve now, pay when you stay

CA $203

CA $240 total

Sep 29 - Sep 30

includes taxes & fees

9/10 Wonderful! (1,362 reviews)

"I would recommend this place to anyone"

Reviewed on Sep 15, 2025

[](https://expedia.ca/Hotel-Search?startDate=29%2F09%2F2025&endDate=30%2F09%2F2025&selected=8474917&PinnedHotelID=8474917&HadPinnedHotel=true&regionId=870620351623675904)

[See all 1,143 properties in Hillside](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=20%2F09%2F2025&endDate=21%2F09%2F2025&regionId=870620351623675904)

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

![Harley-Davidson Museum featuring interior views](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/54000/54544-Harley-Davidson-Museum-Milwaukee.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Harley-Davidson Museum

Delve into the history of one of the world’s most famous motorcycle brands via interactive exhibits, photo galleries, workshops and behind-the-scenes tours.

[](https://expedia.ca/Harley-Davidson-Museum-Milwaukee.d6279040.Vacation-Attraction)

![Milwaukee Art Museum](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/219000/219540-Milwaukee.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Milwaukee Art Museum

Peruse a vast collection of classic European and American art in this gallery that is housed in a striking modern building.

[](https://expedia.ca/Milwaukee-Art-Museum-East-Town.d6068277.Vacation-Attraction)

#### Potawatomi Bingo Casino

Why not roll the dice with a visit to Potawatomi Bingo Casino during your time in Milwaukee? Attend a sporting event or simply enjoy the lively breweries while you're in the area.

[](https://expedia.ca/Potawatomi-Bingo-Casino-Milwaukee.d6335076.Vacation-Attraction)

### Things to do

![Grohmann Museum at Milwaukee School of Engineering](https://mediaim.expedia.com/localexpert/1014613/e2e2dff0-3bca-4049-947d-edf8ec8fd259.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Skip the Line: Museum Admission Ticket - Grohmann Museum

CA $7

per adult

[](https://expedia.ca/things-to-do/skip-the-line-museum-admission-ticket-grohmann-museum.a1014613.activity-details)

![At the Pabst, Captain Frederick Pabst can been seen smoking backstage on a ghost tour of Milwaukee with Brew City Ghosts](https://mediaim.expedia.com/localexpert/44826674/1cb85892-d6aa-4bed-a4d8-8e73fa863666.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Brew City Ghosts: Macabre Milwaukee By US Ghost Adventures

CA $44

per adult

[](https://expedia.ca/things-to-do/brew-city-ghosts-macabre-milwaukee-by-us-ghost-adventures.a44826674.activity-details)

![The Grand Walk: A Self-Guided Audio Tour through Milwaukee](https://mediaim.expedia.com/localexpert/3458981/86be5066-1939-439a-8bf2-ed48f08433ec.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### The Grand Walk: A Self-Guided Audio Tour through Milwaukee

CA $12

per adult

**80%** of travellers recommend

[](https://expedia.ca/things-to-do/the-grand-walk-a-self-guided-audio-tour-through-milwaukee.a3458981.activity-details)

[See all activities in Milwaukee](https://expedia.ca/things-to-do/search?rid=870620351623675904)

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