Five Fields Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*

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Top Holiday Package Deals in Five Fields

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Milwaukee Downtown by IHG

Holiday Inn Express Milwaukee Downtown by IHG

2.5 out of 5
Downtown Milwaukee
Price was CA $1,221, price is now CA $1,053 per person
CA $1,053
per person
May 16 - May 19
found 1 day ago
Roundtrip flight included
Saskatoon (YXE) to Milwaukee (MKE)
9/10 Wonderful! (1,002 reviews)
Staff not super professional dressed and curtesy was just ok. Not great for night time parking. Payment for parking was excessive considering hotel cost.

Reviewed on Mar 2, 2026

Potawatomi Hotel & Casino

Potawatomi Hotel & Casino

4.5 out of 5
Menomonee River Valley
Price was CA $1,349, price is now CA $1,081 per person
CA $1,081
per person
May 16 - May 19
found 1 day ago
Roundtrip flight included
Saskatoon (YXE) to Milwaukee (MKE)
9/10 Wonderful! (1,357 reviews)
Great stay overall! The rooms were clean, modern, and very comfortable with beautiful city views. The casino floor had a fun, energetic vibe with plenty of gaming options. Dining choices were convenient and the staff was friendly and professional. Close to downtown, which made it easy to explore. Would definitely stay again!

Reviewed on Feb 27, 2026

Kinn Guesthouse Bay View

Kinn Guesthouse Bay View

4.5 out of 5
Bay View
Price was CA $1,272, price is now CA $1,087 per person
CA $1,087
per person
May 16 - May 19
found 1 day ago
Roundtrip flight included
Saskatoon (YXE) to Milwaukee (MKE)
9.6/10 Exceptional! (428 reviews)
Scent sensitive people, beware. They use scented detergent on their linens, if you're sensitive to that kind of stuff. The staff was great at fixing my issues, but I took a refund and left after one night. When I arrived, the common area and the room was over 80 degrees. It took hours and several phone calls to work through the issue. I was moved to another room but the heat issue persisted. It wasn't until 3 am that the room finally got to 70 degrees. Also, I carry a white noise machine because hotels can get noisy. But I was still able to hear people banging around in the shared kitchen throughout the entire night. So, after one night of no sleep, I decided to take their offer to refund my second night and let me leave. I just have up on all my plans and went home. But staff and management were dilligent in addressing my issues.

Reviewed on Feb 15, 2026

Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Downtown Milwaukee
Price was CA $1,395, price is now CA $1,192 per person
CA $1,192
per person
May 16 - May 19
found 1 day ago
Roundtrip flight included
Saskatoon (YXE) to Milwaukee (MKE)
9.8/10 Exceptional! (2,425 reviews)
Always a great stay at the St Kate!

Reviewed on Mar 1, 2026

The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
Price was CA $1,570, price is now CA $1,350 per person
CA $1,350
per person
May 16 - May 19
found 1 day ago
Roundtrip flight included
Saskatoon (YXE) to Milwaukee (MKE)
9.2/10 Wonderful! (1,008 reviews)
We love staying at the Iron Horse. The location is convenient, rooms are cool, and they have onsite food and drink options. Trendy atmosphere.

Reviewed on Mar 1, 2026

Where to stay in Five Fields

Find the best Five Fields areas and neighborhoods for the activities you enjoy most. Learn more about Five Fields
Downtown skyline with Buildings along the Milwaukee River, in Milwaukee, Wisconsin.; Shutterstock ID 523595590

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

Five Fields 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 $231 per night from Mar 5 to Mar 6
CA $231
CA $272 total
Mar 5 - Mar 6
includes taxes & fees
9.6/10 Exceptional! (2,018 reviews)
I like that you have absinthe.

Reviewed on Mar 2, 2026

The Pfister Hotel
Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
139 E Kilbourn Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is CA $227 per night from Mar 11 to Mar 12
CA $227
CA $268 total
Mar 11 - Mar 12
includes taxes & fees
9.8/10 Exceptional! (2,580 reviews)
Amazing! So clean and artsy and trendy. We felt like we had escaped to a private world and it was so fun.

Reviewed on Mar 2, 2026

Saint Kate - The Arts Hotel
The Knickerbocker on the Lake

The Knickerbocker on the Lake

3 out of 5
1028 East Juneau Avenue Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is CA $127 per night from Mar 15 to Mar 16
CA $127
CA $149 total
Mar 15 - Mar 16
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
.

Reviewed on Mar 2, 2026

The Knickerbocker on the Lake
See all 1,220 properties in Five Fields
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.
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Frequently asked questions

How much does a Five Fields vacation package cost?
From as low as CA $1,053. Yes, you read that right. Our Five Fields packages are the best way to make your budget stretch further. Combine your flights, hotels and rental car and discover this popular destination.
How do I get a cheap travel package to Five Fields?
Lock in flights that fit in with your schedule, add a hotel room to your booking and watch the savings rack up with a Five Fields vacation package. It's as easy as that! From hotels and flights to tours and rental cars, Expedia is where your cheap vacation begins. And with more than 550 partner airlines and 1,000,000 properties worldwide to pick from, you won't be short of choice.
Where should I stay in Five Fields?
With interesting attractions like Pewaukee Lake Beach and Pewaukee Golf Club in this neighborhood, try to find a hotel situated near either one. Two Brothers Wines is another sight in Five Fields that draws the crowds.
How far in advance should I book my Five Fields vacation?
Travelers are generally able to look up international flights on Expedia within 12 months of the departure date. Booking at the last minute? With a stroke of luck, it's still possible to purchase an affordable ticket only weeks before your journey.
What does an Expedia Five Fields travel package include?
Hotels, rental cars and flights — we have them well covered. With Expedia, you can shape your Five Fields package the way you want. All you have to do is decide just what you need. Once you've made your booking, you can add on fun things like activities and tours. The more you bundle, the bigger your savings!
What should I know before booking a Five Fields travel package?
When you book your flights, hotels and car rentals together, you'll pick up awesome discounts. Whether you're planning a rural escape in a cottage or would rather stay in a convenient hotel in the city, Expedia can help make it happen.
Can I choose my airline with a Five Fields Expedia vacation package?
Yes, the choice is all yours. Expedia has access to more than 550 airlines across the globe, so you can tailor your Five Fields adventure according to your budget and style.
If I'm not able to travel, can I cancel my Five Fields vacation package?
Don't stress if you're rethinking your Five Fields vacation package — it's possible to cancel or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur charges from your hotel, airline or car rental company. We get that your circumstances can change suddenly, so head to our Customer Service Portal if that happens. When you're ready to make changes, we'll be here to help.

Discover the most popular places to visit in Five Fields

Harley-Davidson Museum featuring interior views

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.

Harley-Davidson Museum
Milwaukee Art Museum

Milwaukee Art Museum

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

Things to do

2 Hour Milwaukee Scavenger Hunt Game

Milwaukee Scavenger Hunt Walking Tour and Game

CA $67
per adult
Milwaukee Scavenger Hunt Walking Tour and Game
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.