South Milwaukee Vacations from $460

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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.

The Latest South Milwaukee vacation packages

Price found within the past 48 hours. Click for updated prices.
Kimpton Journeyman Hotel by IHG

Kimpton Journeyman Hotel by IHG

4.5 out of 5
Downtown Milwaukee
Price was $600, price is now $460 per person
$460
per person
Jan 29 - Feb 1
found 11 hours ago
Roundtrip flight included
Denver (DEN) to Milwaukee (MKE)
9.4/10 Exceptional! (1,000 reviews)

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
Price was $727, price is now $499 per person
$499
per person
Jan 29 - Feb 1
found 11 hours ago
Roundtrip flight included
Denver (DEN) to Milwaukee (MKE)
9.6/10 Exceptional! (2,299 reviews)
Staff and amenities are always the highlight of staying. A favorite of ours whether it’s for an overnight or weekend away. Truly unique

Reviewed on Nov 3, 2026

The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
Price was $615, price is now $468 per person
$468
per person
Jan 29 - Feb 1
found 11 hours ago
Roundtrip flight included
Denver (DEN) to Milwaukee (MKE)
9.2/10 Wonderful! (1,378 reviews)
Great location and bar! Loved getting a couples massage and a great workout space! It was such a nice quiet area and delicious food near by!

Reviewed on Nov 4, 2026

Kinn Guesthouse Downtown

Kinn Guesthouse Downtown

4.5 out of 5
Downtown Milwaukee
Price was $788, price is now $616 per person
$616
per person
Jan 29 - Feb 1
found 11 hours ago
Roundtrip flight included
Denver (DEN) to Milwaukee (MKE)
9.4/10 Exceptional! (444 reviews)
Awesome space. Decor was amazing and bed super comfortable.

Reviewed on Nov 2, 2026

Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Downtown Milwaukee
Price was $684, price is now $539 per person
$539
per person
Jan 29 - Feb 1
found 11 hours ago
Roundtrip flight included
Denver (DEN) to Milwaukee (MKE)
9.8/10 Exceptional! (2,742 reviews)
Beautiful hotel close to everything if you're going to a show at the pabst theater this is the place. Can't say enough good things about this place we had a great time stay there for the Blue October concert so happens the Brewers won the world series while we were there we had a blast

Reviewed on Nov 4, 2026

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Stay near popular South Milwaukee attractions

South Milwaukee Performing Arts Center

9.0/10 (2 reviews)
This intimate 786-seat theater offers diverse performances with excellent acoustics and unobstructed views. Arrive early to explore the venue before enjoying world-class music, theater, or dance.
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What to do in South Milwaukee

Milwaukee Morbid Mirrorlight Ghost Tours

Milwaukee Morbid Mirrorlight Ghost Tours

$26
per adult
Milwaukee Morbid Mirrorlight Ghost Tours
Milwaukee Historic Downtown Self Guided Walking Tour

Milwaukee Historic Downtown Self Guided Walking Tour

$10
per adult
Milwaukee Historic Downtown Self Guided Walking Tour
City of Neighborhoods: A Self-Guided Audio Tour in Milwaukee

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

$8
per adult
City of Neighborhoods: A Self-Guided Audio Tour in Milwaukee
See all activities in South Milwaukee

South Milwaukee Hotel Deals

Hyatt Regency Milwaukee

Hyatt Regency Milwaukee

4 out of 5
333 W Kilbourn Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
$79 nightly
The price is $93 total per night from Nov 23 to Nov 24
$93 total
Nov 23 - Nov 24
Total with taxes and fees
Hyatt Regency Milwaukee
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
$87 nightly
The price is $100 total per night from Nov 12 to Nov 13
$100 total
Nov 12 - Nov 13
Total with taxes and fees
8.4/10 Very Good! (1,323 reviews)
"Sinners blocked in the room was supposed to be fixed but wasn’t"

Reviewed on Nov 3, 2026

Sheraton Milwaukee Brookfield Hotel
Drury Plaza Hotel Milwaukee Downtown

Drury Plaza Hotel Milwaukee Downtown

4 out of 5
700 N. Water Street Milwaukee WI
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $131 total per night from Nov 30 to Dec 1
$131 total
Nov 30 - Dec 1
Total with taxes and fees
Drury Plaza Hotel Milwaukee Downtown
See all 1,185 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.

Find the Best South Milwaukee Vacation Packages

South Milwaukee Essential Information

Language
English
Currency
U.S dollars
Closest Airport
General Mitchell Intl. Airport (MKE)
Population
21,200
Top Sights
Harley-Davidson Museum, Milwaukee Art Museum and Riverside Theater

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Frequently asked questions

How much does a South Milwaukee vacation package cost?
You can snap up a vacation package to this popular destination from $460 on Expedia. But how much your vacation to South Milwaukee costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to South Milwaukee?
You can usually find reduced prices and greater availability in January, October and December. Check out our cheap South Milwaukee vacation packages and you could get some excellent off-season deals.
How many days is enough for South Milwaukee?
Usually, a handful of days is enough to check out the top sights during your South Milwaukee vacation. But if you prefer to have some time to chill out or take day tours, consider extending your trip.
Is it worth booking a vacation package to South Milwaukee?
Well known for its hiking, golfing and a host of other highlights, you can be assured South Milwaukee is a good vacation destination. Some of the top attractions to add to your itinerary? Don't miss South Milwaukee Downtown Market and South Milwaukee Performing Arts Center during your South Milwaukee vacation.
How to find the best South Milwaukee package deals?
Bagging a cheap South Milwaukee package deal is a cinch with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, add a couple of filters and see what's available. You can tailor your search by "Amenities," "Property type," "Popular locations" and more. Sort the results by "Price: low to high" to view the most affordable South Milwaukee package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are typically lower.
Is it cheaper to book a South Milwaukee vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking flights and stays individually. Better still, you can customize your South Milwaukee trip to fit your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to South Milwaukee?
If you've got your South Milwaukee vacation dates confirmed, book early to score some outstanding deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are great for quick escapes.
Does Expedia offer Book Now, Pay Later South Milwaukee vacation packages?
Jet off on your perfect trip to South Milwaukee with Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or wait until the next payday — we've teamed up with online lender Affirm to offer you flexibility and choice. Our vacation packages with payment plans allow you to spread the cost over 3, 6 or 12 months. With no late payment fees or hidden charges, you can easily budget for your trip and snap up bargains before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.