Hillside Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.
The Pfister Hotel
Downtown Milwaukee
Price was CA $1,619, price is now CA $967 per person
CA $967
per person
Jul 30 - Aug 2
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Milwaukee (MKE)
9.6/10 Exceptional! (2,134 reviews)
My wife and I spent a weekend at the Pfister for a wedding celebration (off property). Our room was impeccably clean and the paragon of modernity: the bathroom had more electronics than our home entertainment system! From our window on the 22nd floor we could see the lake and Summer Fest festivities. Customer service is outstanding across the entire property. The location is excellent - 3 blocks from the lake front which is fabulous. The Art Museum is fantastic! I highly recommend this property!
Reviewed on Jun 22, 2026
Saint Kate - The Arts Hotel
Downtown Milwaukee
Price was CA $1,130, price is now CA $924 per person
CA $924
per person
Sep 11 - Sep 13
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Milwaukee (MKE)
9.8/10 Exceptional! (2,655 reviews)
The location of this property was within walking distance of almost everything you woul want to do in Milwuakee. The staff was always helpful and had great suggestions on where to visit ans always helpful with whatever we needed. The coolest hotel we have stayed at with all the art in the galleries and little details in each room and on each floor.
Reviewed on Jun 21, 2026
Dubbel Dutch
Downtown Milwaukee
Price was CA $1,020, price is now CA $855 per person
CA $855
per person
Sep 11 - Sep 13
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Milwaukee (MKE)
9.2/10 Wonderful! (148 reviews)
Excellent property! Near to everything we wanted to do, and very walkable!! Loved the building! Beautiful!!
Reviewed on Jun 21, 2026
The Iron Horse Hotel
Fifth Ward
Price was CA $1,081, price is now CA $939 per person
CA $939
per person
Sep 11 - Sep 13
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Milwaukee (MKE)
9.2/10 Wonderful! (1,162 reviews)
The staff was very friendly and kind and the rooms were comfortable!
Reviewed on Jun 21, 2026
Where to stay in Hillside
Find the best Hillside areas and neighborhoods for the activities you enjoy most. Learn more about Hillside
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.
Hillside Hotel Deals
Potawatomi Hotel & Casino
1611 West Canal Street Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is CA $223 per night from Jun 29 to Jun 30
CA $223
CA $263 total
Jun 29 - Jun 30
includes taxes & fees
9.2/10 Wonderful! (1,552 reviews)
"Clean staff was helpful"
Reviewed on Jun 21, 2026
The Pfister Hotel
424 E Wisconsin Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is CA $251 per night from Jul 7 to Jul 8
CA $251
CA $296 total
Jul 7 - Jul 8
includes taxes & fees
9.6/10 Exceptional! (2,140 reviews)
"My wife and I spent a weekend at the Pfister for a wedding celebration (off property). Our room was impeccably clean and the paragon of modernity: the bathroom had more electronics than our home entertainment system! From our window on the 22nd floor we could see the lake and Summer Fest festivities. ..."
Reviewed on Jun 22, 2026
Sheraton Milwaukee Brookfield Hotel
375 S Moorland Rd Brookfield WI
Fully refundableReserve now, pay when you stay
The price is CA $146 per night from Jul 5 to Jul 6
CA $146
CA $168 total
Jul 5 - Jul 6
includes taxes & fees
8.4/10 Very Good! (908 reviews)
"Awesome"
Reviewed on Jun 21, 2026
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.
Discover the most popular places to visit in Hillside
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.
Milwaukee Art Museum
Peruse a vast collection of classic European and American art in this gallery that is housed in a striking modern building.
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.
Things to do
Small Group Kayak Tour of Skyline in Milwaukee
CA $115
per adult
City of Neighborhoods: A Self-Guided Audio Tour in Milwaukee
CA $11
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.