Westown Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Geraldine Soh

  • 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

Top Holiday Package Deals in Westown

Price found within the past 48 hours. Click for updated prices.
Sheraton Milwaukee Brookfield Hotel

Sheraton Milwaukee Brookfield Hotel

3.5 out of 5
Price was CA $1,275, price is now CA $989 per person
CA $989
per person
Aug 25 - Aug 29
found 23 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Milwaukee (MKE)
8.4/10 Very good! (925 reviews)
Room was clean and beds were comfortable Very convenient area with good restaurants nearby Staff very helpful

Reviewed on Jul 10, 2026

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
Price was CA $2,231, price is now CA $1,341 per person
CA $1,341
per person
Sep 11 - Sep 14
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Milwaukee (MKE)
9.6/10 Exceptional! (2,139 reviews)
Beautiful property. Every staff member--from front desk, bar, restaurant, housekeeping, concierge,to bellhops, were pleasant, professional & helpful. Our room was comfortable, clean & quiet. The location was perfect, just a short walk from the art museum. Would certainly stay here again.

Reviewed on Jul 9, 2026

Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Downtown Milwaukee
Price was CA $1,330, price is now CA $1,060 per person
CA $1,060
per person
Sep 11 - Sep 14
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Milwaukee (MKE)
9.8/10 Exceptional! (2,652 reviews)
Nice clean room. Fun hotel with great food and next to the theatre!

Reviewed on Jul 9, 2026

The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
Price was CA $1,293, price is now CA $1,040 per person
CA $1,040
per person
Sep 11 - Sep 14
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Milwaukee (MKE)
9.2/10 Wonderful! (1,192 reviews)
No laundry facilities

Reviewed on Jul 10, 2026

Kinn Guesthouse Bay View

Kinn Guesthouse Bay View

4.5 out of 5
Bay View
Price was CA $1,450, price is now CA $1,204 per person
CA $1,204
per person
Sep 11 - Sep 14
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Milwaukee (MKE)
9.4/10 Exceptional! (481 reviews)
Great place! Loved that bar and restaurant on site too.

Reviewed on Jul 3, 2026

Where to stay in Westown

Find the best Westown areas and neighborhoods for the activities you enjoy most. Learn more about Westown
A river with a city skyline, including a tall building with a pointed roof, and a park with yellow trees.

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 hotels in Downtown Milwaukee

Westown Hotel Deals

Hyatt Regency Milwaukee

Hyatt Regency Milwaukee

4 out of 5
333 W Kilbourn Ave Milwaukee WI
The price is CA $132 per night from Aug 9 to Aug 10
CA $132
CA $155 total
Aug 9 - Aug 10
includes taxes & fees
8.6/10 Excellent! (1,345 reviews)
"Staff was very helpful and polite."

Reviewed on Jul 9, 2026

Hyatt Regency Milwaukee
The Marc Hotel

The Marc Hotel

2 out of 5
640 North 6th Street Milwaukee WI
The price is CA $153 per night from Aug 9 to Aug 10
CA $153
CA $180 total
Aug 9 - Aug 10
includes taxes & fees
8.8/10 Excellent! (114 reviews)
"centrally located and close to everything"

Reviewed on Jul 10, 2026

The Marc Hotel
Hilton Milwaukee

Hilton Milwaukee

4 out of 5
509 W Wisconsin Ave Milwaukee WI
The price is CA $192 per night from Aug 10 to Aug 11
CA $192
CA $226 total
Aug 10 - Aug 11
includes taxes & fees
8.6/10 Excellent! (1,188 reviews)
"The staff needs to let the guest know about parking. I was very disappointed to find out that I was charged to park inside the hotel at $43.00 a day. As a guest I would think parking would be free."

Reviewed on Jul 9, 2026

Hilton Milwaukee
See all 1,167 properties in Westown
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

Frequently asked questions

How much does a Westown vacation package cost?
Our Westown packages, which begin at just CA $989, are an easy way to save loads of cash. Select your favorite hotels, flights and rental car to create a custom-built escape.
How do I get a cheap travel package to Westown?
Secure flights that suit your schedule, add a hotel room to your booking and see how much you save with a Westown vacation package. It's as easy as that! From flights and hotels to activities and rental cars, Expedia makes traveling on the cheap easy. And with over 550 air carriers and 1,000,000 properties throughout the world to choose from, you won't be short of choice.
Where should I stay in Westown?
A trip to Westown has to include Milwaukee Art Museum and American Family Field. Stay somewhere close by for quick access to these fantastic sights.
What are the top hotels in Westown?
Get your vacation off to a good start by locking in a room at Frontdesk Mke Lofts Downtown Milwaukee. It's one of most sought-after properties in Westown. Another welcoming option is Kasa Westown Milwaukee.
How far in advance should I book my Westown vacation?
Reserving your flight early with Expedia means one less thing to worry about. A number of air carriers advertise prices up to a year in advance. This is usually the cheapest time to book. If circumstances have left you booking late, low prices to Westown sometimes emerge a few weeks before departure.
What does an Expedia Westown travel package include?
Car rentals, flights and hotels — we connect you to all the best deals. All you have to do is pick your ideal combination. Once you've made your booking, you can add on the exciting stuff like activities and tours. Our travel packages make it simple to customize an awesome Westown trip.
What should I know before booking a Westown travel package?
When you book your hotels, flights and car rentals together, you'll walk away with amazing discounts. Whether you're organizing a wilderness getaway in a cabin or want to stay in a convenient hotel in the city, Expedia can make it happen for less.
Can I choose my airline with a Westown Expedia vacation package?
You sure can. We have more than 550 airline partners worldwide, so opt for the carrier that matches your budget and traveling style.
If I'm not able to travel, can I cancel my Westown vacation package?
It's difficult to predict what the future holds, so it's comforting to know that you can change or cancel your Westown vacation package. If your booking was made in the last 24 hours, you may be eligible for a refund. If it's an older booking, your airline, hotel or car rental company may charge a fee. Check our Customer Service Portal to learn more.

Stay near popular Westown attractions

A cityscape with a variety of buildings, including a prominent white structure with a curved roof, a tall tower, and a mix of older and modern architecture.

Fiserv Forum

9.2/10 (2,312 reviews)
Catch an event at Fiserv Forum during your trip to Milwaukee. Attend a sporting event or simply enjoy the lively breweries while you're in the area.
See properties

Things to do

Small Group Kayak Tour of Skyline in Milwaukee

Small Group Kayak Tour of Skyline in Milwaukee

CA $118
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 Milwaukee
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.