Title: Hillside Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $1,249 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. ![Potawatomi Hotel & Casino](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474917/2e421f60_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Potawatomi Hotel & Casino Menomonee River Valley CA $1,249 per person Apr 11 - Apr 18 found 24 hours ago Roundtrip non-stop flight included Edmonton (YEG) to Milwaukee (MKE) 9/10 Wonderful! (1,400 reviews) Online check in was great Reviewed on Mar 3, 2026 ![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 $1,297 per person Apr 11 - Apr 18 found 24 hours ago Roundtrip non-stop flight included Edmonton (YEG) to Milwaukee (MKE) 9.6/10 Exceptional! (428 reviews) Scent sensitive people, beware. They use scented detergent on their linens, if you're sensitive to that kind of stuff. The staff was great at fixing my issues, but I took a refund and left after one night. When I arrived, the common area and the room was over 80 degrees. It took hours and several phone calls to work through the issue. I was moved to another room but the heat issue persisted. It wasn't until 3 am that the room finally got to 70 degrees. Also, I carry a white noise machine because hotels can get noisy. But I was still able to hear people banging around in the shared kitchen throughout the entire night. So, after one night of no sleep, I decided to take their offer to refund my second night and let me leave. I just have up on all my plans and went home. But staff and management were dilligent in addressing my issues. Reviewed on Feb 15, 2026 ![Holiday Inn Express Milwaukee Downtown by IHG](https://images.trvl-media.com/lodging/58000000/57140000/57132500/57132464/cf4024e5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Holiday Inn Express Milwaukee Downtown by IHG Downtown Milwaukee CA $1,532 per person Apr 11 - Apr 18 found 24 hours ago Roundtrip non-stop flight included Edmonton (YEG) to Milwaukee (MKE) 9/10 Wonderful! (1,000 reviews) Staff not super professional dressed and curtesy was just ok. Not great for night time parking. Payment for parking was excessive considering hotel cost. Reviewed on Mar 2, 2026 ![The Iron Horse Hotel](https://images.trvl-media.com/lodging/3000000/2100000/2097200/2097106/w1201h762x12y0-0e8e5e6d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Iron Horse Hotel Fifth Ward CA $1,597 per person Apr 11 - Apr 18 found 24 hours ago Roundtrip non-stop flight included Edmonton (YEG) to Milwaukee (MKE) 9.2/10 Wonderful! (1,023 reviews) We love staying at the Iron Horse. The location is convenient, rooms are cool, and they have onsite food and drink options. Trendy atmosphere. Reviewed on Mar 1, 2026 ![Hampton Inn & Suites Milwaukee Downtown](https://images.trvl-media.com/lodging/1000000/470000/463900/463898/1a6e9416_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hampton Inn & Suites Milwaukee Downtown Westown CA $1,691 per person Apr 11 - Apr 18 found 24 hours ago Roundtrip non-stop flight included Edmonton (YEG) to Milwaukee (MKE) 6.6/10 (1,003 reviews) After the battery went out in our door for the key card, we got moved to the smaller queen room next door, even though staff on site said they were upgrading us from our already king room. Which we were charged king room price both nights even tho we didn’t get to stay in it nor were able to access our luggage. Staff was friendly and apologized for the hassle. Hot tub was Luke warm at best, but the breakfast was great and the GM was able to give us great recommendations for hidden gems that we enjoyed. Reviewed on Mar 4, 2026 ## 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) ![Downtown skyline with Buildings along the Milwaukee River, in Milwaukee, Wisconsin.; Shutterstock ID 523595590](https://images.trvl-media.com/place/6059651/1182062a-a02d-493d-b9fe-49d298b5def0.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) ![96144781](https://images.trvl-media.com/place/6059657/3d426080-e9b2-426a-9651-cd836ecf4e89.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Wauwatosa Wauwatosa is known for its abundant dining options, and you can plan a trip to Mayfair Mall and The Mayfair Collection 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://images.trvl-media.com/place/6068277/f9df43ae-9037-4ed0-8755-204129016a40.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) ![The Milwaukee Riverwalk System began in 1993, as a means to offer public access to the river. Once complete, the Riverwalk will extend 3.1 miles along both sides of the Milwaukee River, from the site of the former North Avenue Dam, through Downtown and the Historic Third Ward to Lake Michigan. #LikeALocal](https://images.trvl-media.com/place/2325/e14aea82-f689-465b-a1de-58418a74a9ab.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Westown 2 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) ![Ferris Wheel Spinning Round Illuminated in Night Sky](https://images.trvl-media.com/place/7685/c9ddb0cf-39d4-4515-b334-9d7a3f73ea61.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### West Allis West Allis is noteworthy for its restaurants, and you can make a stop at top attractions like Milwaukee Mile Speedway and Wisconsin State Fair Park. [Find hotel + flight trips in West Allis](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=West%20Allis&DestID=7685&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ## Hillside Hotel Deals ![Saint Kate - The Arts Hotel](https://images.trvl-media.com/lodging/1000000/30000/23300/23253/3a9f7f5d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Saint Kate - The Arts Hotel 139 E Kilbourn Ave Milwaukee WI CA $228 CA $268 total Mar 11 - Mar 12 includes taxes & fees 9.8/10 Exceptional! (2,583 reviews) Great classy little hotel close to theaters. Attentive and not obtrusive staff. Great vibe and interesting decor. Air handling in rooms is top notch. Reviewed on Mar 4, 2026 [](https://expedia.ca/Hotel-Search?startDate=11%2F03%2F2026&endDate=12%2F03%2F2026&selected=23253&PinnedHotelID=23253&HadPinnedHotel=true®ionId=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 CA $137 CA $161 total Mar 10 - Mar 11 includes taxes & fees 9.6/10 Exceptional! (2,096 reviews) Everything was great Reviewed on Mar 3, 2026 [](https://expedia.ca/Hotel-Search?startDate=10%2F03%2F2026&endDate=11%2F03%2F2026&selected=32501737&PinnedHotelID=32501737&HadPinnedHotel=true®ionId=870620351623675904) ![Potawatomi Hotel & Casino](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474917/2e421f60_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 $239 total Mar 22 - Mar 23 includes taxes & fees 9/10 Wonderful! (1,407 reviews) Online check in was great Reviewed on Mar 3, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F03%2F2026&endDate=23%2F03%2F2026&selected=8474917&PinnedHotelID=8474917&HadPinnedHotel=true®ionId=870620351623675904) [See all 1,142 properties in Hillside](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=05%2F03%2F2026&endDate=06%2F03%2F2026®ionId=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://images.trvl-media.com/place/6279040/52cab404-1cac-4be9-bd03-910682810f03.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Harley-Davidson Museum 5/5(13 reviews) 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-Menomonee-River-Valley.d6279040.Vacation-Attraction) ![Milwaukee Art Museum](https://images.trvl-media.com/place/6068277/1fe18a15-7f30-4ecc-8164-b72f9b7fcfed.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Milwaukee Art Museum 5/5(12 reviews) 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-Menomonee-River-Valley.d6335076.Vacation-Attraction) ### Things to do ![2 Hour Milwaukee Scavenger Hunt Game](https://mediaim.expedia.com/localexpert/49296611/4017c436-a1bb-44c8-9945-447fa08e21b1.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Milwaukee Scavenger Hunt Walking Tour and Game CA $67 per adult [](https://expedia.ca/things-to-do/milwaukee-scavenger-hunt-walking-tour-and-game.a49296611.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.