Five Fields Vacation Packages

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    Save up to CA $4,200 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.
The Pfister Hotel

The Pfister Hotel

Downtown Milwaukee
CA $860
per person
Nov 20 - Nov 23
found 13 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Milwaukee (MKE)
9.6/10 Exceptional! (2,229 reviews)
The Iron Horse Hotel

The Iron Horse Hotel

Fifth Ward
CA $893
per person
Nov 20 - Nov 23
found 13 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Milwaukee (MKE)
9.2/10 Wonderful! (1,305 reviews)
Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

Downtown Milwaukee
CA $1,451
per person
Oct 17 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Milwaukee (MKE)
9.8/10 Exceptional! (2,674 reviews)
Kinn Guesthouse Bay View

Kinn Guesthouse Bay View

Bay View
CA $882
per person
Nov 20 - Nov 23
found 13 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Milwaukee (MKE)
9.4/10 Exceptional! (500 reviews)
Potawatomi Hotel & Casino

Potawatomi Hotel & Casino

Menomonee River Valley
CA $1,590
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Milwaukee (MKE)
9.2/10 Wonderful! (1,797 reviews)
Casino nice room

Reviewed on Sep 2, 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
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.

A river with buildings reflecting on the water, a bridge, and a tall building with a green roof.

West Allis

1 out of top 10 points of interest in this area

West Allis is noteworthy for its restaurants, and you can make a stop at top attractions like Milwaukee Mile Speedway and Wisconsin State Fair Park.

A stone bridge with a wooden walkway surrounded by lush greenery.

Wauwatosa

Wauwatosa is known for its abundant dining options, and you can plan a trip to Mayfair Mall and The Mayfair Collection while you're in town.

A river with boats, a marina, and historic buildings along the waterfront.

Historic Third Ward

1 out of top 10 points of interest in this area

Experience a historic warehouse district with a mix of specialty shops, art galleries, and restaurants. Visit the Milwaukee Institute of Art and Design, and enjoy year-round gourmet options at the Milwaukee Public Market, easily accessible via The Hop.

A pedestrian bridge over a river with a city skyline in the background, including a prominent bank building.

East Town

East Town is highly notable for its fantastic nightlife, and you might want to visit top sights like Lake Michigan and Veteran's Park. See more of Milwaukee by jumping on the metro at Michigan & Jackson Tram Stop or Clybourn & Jefferson Tram Stop.

Five Fields Hotel Deals

The Pfister Hotel

The Pfister Hotel

424 E Wisconsin Ave Milwaukee WI
CA $270
CA $318 total
Sep 27 - Sep 28
includes taxes & fees
The Pfister Hotel
AmericInn by Wyndham Brookfield

AmericInn by Wyndham Brookfield

16865 W Bluemound Rd Brookfield WI
Fully refundableReserve now, pay when you stay
CA $108
CA $125 total
Sep 9 - Sep 10
includes taxes & fees
AmericInn by Wyndham Brookfield
Hyatt Regency Milwaukee

Hyatt Regency Milwaukee

333 W Kilbourn Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
CA $129
CA $152 total
Sep 29 - Sep 30
includes taxes & fees
Hyatt Regency Milwaukee
See all 1,285 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.

Frequently asked questions

How much does a Five Fields vacation package cost?
From as low as CA $860. 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.

Things to do

View of E. Wisconsin Ave. looking towards Lake Michigan

Downtown Milwaukee Walking Tour

CA $22
per adult
Downtown Milwaukee Walking Tour
Milwaukee Food Tour with 5 Local Favorites Tastings & Secret Dish

Milwaukee Food Tour with 5 Local Favorites Tastings & Secret Dish

CA $141
per adult
Milwaukee Food Tour with 5 Local Favorites Tastings & Secret Dish
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
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.