South Milwaukee Vacation Packages

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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.
Kinn Guesthouse Bay View

Kinn Guesthouse Bay View

4.5 out of 5
Bay View
Price was CA $1,285, price is now CA $995 per person
CA $995
per person
Jun 1 - Jun 5
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
9.4/10 Exceptional! (456 reviews)
The room was very spacious and clean. We loved the convenience of the area and the many amenities es provided on site. The team did an amazing job of communicating with rapid speed.

Reviewed on Mar 23, 2026

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
Price was CA $2,061, price is now CA $1,484 per person
CA $1,484
per person
Jun 27 - Jun 29
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Milwaukee (MKE)
9.6/10 Exceptional! (2,072 reviews)
Lovely old yet modern hotel. Great location to everything in Milwaukee.

Reviewed on Apr 19, 2026

Holiday Inn Express Milwaukee Downtown by IHG

Holiday Inn Express Milwaukee Downtown by IHG

2.5 out of 5
Downtown Milwaukee
Price was CA $1,770, price is now CA $1,413 per person
CA $1,413
per person
Jun 24 - Jun 27
found 21 hours ago
Roundtrip flight included
Edmonton (YEG) to Milwaukee (MKE)
9/10 Wonderful! (1,009 reviews)
I was very pleased with Holiay Inn downtown Milwaukee. All the staff from the woman with long gray hair at the front desk to the valets were very friendly and helpful. The bed was very comfortable. I especially appreciated that the water got hot very fast, rather than having to run it for several minuets. Location is very walkable and safe; I recommend Topelo Honey and the Public Market.

Reviewed on Apr 20, 2026

Potawatomi Hotel & Casino

Potawatomi Hotel & Casino

4.5 out of 5
Menomonee River Valley
Price was CA $1,639, price is now CA $1,318 per person
CA $1,318
per person
Jun 24 - Jun 27
found 21 hours ago
Roundtrip flight included
Edmonton (YEG) to Milwaukee (MKE)
9.2/10 Wonderful! (1,435 reviews)
I was hoping there was a spa

Reviewed on Apr 20, 2026

The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
Price was CA $1,655, price is now CA $1,363 per person
CA $1,363
per person
Jun 27 - Jun 29
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Milwaukee (MKE)
9.2/10 Wonderful! (1,057 reviews)
Great location. Decor was hip, fun and artistic. Room was clean. Bed and pillow comfy. Room was a little worn.

Reviewed on Apr 20, 2026

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South Milwaukee Hotel Deals

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 $232 per night from May 19 to May 20
CA $232
CA $274 total
May 19 - May 20
includes taxes & fees
9.6/10 Exceptional! (2,081 reviews)
Lovely old yet modern hotel. Great location to everything in Milwaukee.

Reviewed on Apr 19, 2026

The Pfister Hotel
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 $203 per night from Apr 27 to Apr 28
CA $203
CA $239 total
Apr 27 - Apr 28
includes taxes & fees
9.2/10 Wonderful! (1,431 reviews)
I was hoping there was a spa

Reviewed on Apr 20, 2026

Potawatomi Hotel & Casino
Drury Plaza Hotel Milwaukee Downtown

Drury Plaza Hotel Milwaukee Downtown

3 out of 5
700 N. Water Street Milwaukee WI
The price is CA $177 per night from Apr 26 to Apr 27
CA $177
CA $209 total
Apr 26 - Apr 27
includes taxes & fees
9.6/10 Exceptional! (2,169 reviews)
The place was fine the room was big n comfy and comfy beds

Reviewed on Apr 19, 2026

Drury Plaza Hotel Milwaukee Downtown
See all 1,215 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
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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

Milwaukee 1-Day Tour from Chicago

Milwaukee,Harley-Davidson Museum, Miller Brewery 1-Day Trip from Chicago

CA $172
per traveller
Milwaukee,Harley-Davidson Museum, Miller Brewery 1-Day Trip from Chicago
The Ghosts of Milwaukee & the Haunted Third Ward: Private Tour

The Ghosts of Milwaukee & the Haunted Third Ward: Private Tour

CA $358
per adult
The Ghosts of Milwaukee & the Haunted Third Ward: Private Tour
See all activities in South Milwaukee

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