South Milwaukee Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Eric & Kristy's Adventures

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

Your South Milwaukee Vacation

When a fun city break is calling, answer it with a South Milwaukee vacation package. The neighborhood of Historic Third Ward, which is great for shopping, festivals and history, makes a wonderful base for your adventures. A trip to South Milwaukee is a great opportunity to do a bit of sightseeing. Check out popular attractions like South Milwaukee Performing Arts Center, South Milwaukee Downtown Market and Just 4 Ewe. A few clicks is all it takes to put together a tailor-made South Milwaukee vacation on Expedia.

Top South Milwaukee Vacation Deals

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

The Ingleside Hotel

4 out of 5
Price was CA $835, price is now CA $734 per person
CA $734
per person
Sep 11 - Sep 13
found 23 hours ago
Roundtrip flight included
Vancouver (YVR) to Milwaukee (MKE)
8.6/10 Excellent! (818 reviews)
Room was clean, staff was helpful with my child's allergies.

Reviewed on Jun 20, 2026

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
Price was CA $1,619, price is now CA $967 per person
CA $967
per person
Jul 30 - Aug 2
found 12 hours ago
Roundtrip flight included
Toronto (YTO) to Milwaukee (MKE)
9.6/10 Exceptional! (2,134 reviews)
Beautiful, historic hotel in downtown Milwaukee. Excellent location, allowing us to walk to various attractions. The staff was always friendly and helpful.

Reviewed on Jun 17, 2026

Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Downtown Milwaukee
Price was CA $1,130, price is now CA $924 per person
CA $924
per person
Sep 11 - Sep 13
found 23 hours 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

Dubbel Dutch

3 out of 5
Downtown Milwaukee
Price was CA $1,020, price is now CA $855 per person
CA $855
per person
Sep 11 - Sep 13
found 23 hours 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

The Iron Horse Hotel

4 out of 5
Fifth Ward
Price was CA $1,081, price is now CA $939 per person
CA $939
per person
Sep 11 - Sep 13
found 23 hours ago
Roundtrip flight included
Vancouver (YVR) to Milwaukee (MKE)
9.2/10 Wonderful! (1,166 reviews)
We loved the Iron Horse!! Location was fantastic, we walked to several places from the hotel. The room was gorgeous and huge, very comfortable. I agonized over where to stay in milwaukee and really happy with this hotel. The lobby has an oddly strong scent of aftershave that made us laugh. The valet are really friendly, front desk was great too!

Reviewed on Jun 20, 2026

Ready to book your vacation to South Milwaukee?

 

Choose your dates

South Milwaukee Hotel Deals

Potawatomi Hotel & Casino

Potawatomi Hotel & Casino

4.5 out of 5
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! (1,547 reviews)
"Everything"

Reviewed on Jun 21, 2026

Potawatomi Hotel & Casino
The Pfister Hotel

The Pfister Hotel

4.5 out of 5
424 E Wisconsin Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is CA $313 per night from Jul 5 to Jul 6
CA $313
CA $369 total
Jul 5 - Jul 6
includes taxes & fees
9.6/10 Exceptional! (2,137 reviews)
"Great communication from the hotel manager from the very beginning. The hotel is everything you would expect it to be. Friendly staff, clean rooms, and super comfy beds! Cafe serves Starbucks coffee."

Reviewed on Jun 20, 2026

The Pfister Hotel
Sheraton Milwaukee Brookfield Hotel

Sheraton Milwaukee Brookfield Hotel

3.5 out of 5
375 S Moorland Rd Brookfield WI
Fully refundableReserve now, pay when you stay
The price is CA $150 per night from Jun 28 to Jun 29
CA $150
CA $173 total
Jun 28 - Jun 29
includes taxes & fees
8.4/10 Very Good! (904 reviews)
"Very helpful staff check was a breeze"

Reviewed on Jun 21, 2026

Sheraton Milwaukee Brookfield Hotel
See all 1,206 properties in South Milwaukee
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in South Milwaukee

Harley-Davidson Museum

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.

Harley-Davidson Museum
Milwaukee Art Museum

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.

Milwaukee Art Museum

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.

Potawatomi Bingo Casino

What to do in South Milwaukee

Small Group Kayak Tour of Skyline in Milwaukee

Small Group Kayak Tour of Skyline in Milwaukee

CA $115
per adult
Small Group Kayak Tour of Skyline in Milwaukee
City of Neighborhoods: A Self-Guided Audio Tour in Milwaukee

City of Neighborhoods: A Self-Guided Audio Tour in Milwaukee

CA $11
per adult
City of Neighborhoods: A Self-Guided Audio Tour in Milwaukee
See all activities in South Milwaukee

Explore a world of travel with Expedia

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