Five Fields Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • 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
Price found within the past 48 hours. Click for updated prices.
  • Deluxe King
    Aug 13 - Aug 15

    Saint Kate - The Arts Hotel + Flight

    Downtown Milwaukee
    2 nights
    4.0 star property
    9.8/10 - Exceptional (2,640 reviews)
    "Really fun, cool place!"
    Reviewed June 6, 2026
    Roundtrip • Toronto (YYZ) - Milwaukee (MKE)
    YYZ - MKE • 1 stop MKE - YYZ • 1 stop
    CA $1,051
    CA $921
    per traveller
    found 1 day ago
    Saint Kate - The Arts Hotel
  • Lobby
    Aug 13 - Aug 15

    The Pfister Hotel + Flight

    Downtown Milwaukee
    2 nights
    4.5 star property
    9.6/10 - Exceptional (2,124 reviews)
    "The entire staff we encountered were helpful and kind! From checking in, to valet, to the cafe, to room service, we had a great experience with everything."
    Reviewed June 6, 2026
    Roundtrip • Toronto (YYZ) - Milwaukee (MKE)
    YYZ - MKE • 1 stop MKE - YYZ • 1 stop
    CA $1,435
    CA $1,057
    per traveller
    found 1 day ago
    The Pfister Hotel
  • 3 restaurants; lunch, dinner, and brunch served
    Aug 13 - Aug 15

    The Iron Horse Hotel + Flight

    Fifth Ward
    2 nights
    4.0 star property
    9.2/10 - Wonderful (1,163 reviews)
    "We will be going back."
    Reviewed June 5, 2026
    Roundtrip • Toronto (YYZ) - Milwaukee (MKE)
    YYZ - MKE • 1 stop MKE - YYZ • 1 stop
    CA $1,248
    CA $1,093
    per traveller
    found 1 day ago
    The Iron Horse Hotel
  • Fridge, microwave, oven, dishwasher
    Aug 13 - Aug 15

    Kinn Guesthouse Bay View + Flight

    Bay View
    2 nights
    4.5 star property
    9.4/10 - Exceptional (468 reviews)
    "Kinn Guesthouses are a great place to stay if you don’t mind no front desk and coded entries. We’ve found them to have large rooms which are tastefully decorated, comfortable and quiet. The common area is stocked with teas, coffee and breakfast cereals which you can use. Be sure to contact property directly before you arrive for entry code. Expedia apparently does not share contact information with Kinn so you can access the room. Therefore they have no way to send you this..."
    Reviewed May 29, 2026
    Roundtrip • Toronto (YYZ) - Milwaukee (MKE)
    YYZ - MKE • 1 stop MKE - YYZ • 1 stop
    CA $1,153
    CA $1,049
    per traveller
    found 1 day ago
    Kinn Guesthouse Bay View
  • Exterior
    Aug 13 - Aug 15

    Kinn Guesthouse Downtown + Flight

    Downtown Milwaukee
    2 nights
    4.5 star property
    9.4/10 - Exceptional (354 reviews)
    "This was an incredible place to stay! We were all super impressed with everything! I was in a great location as well. Close to so many places. Would definitely stay again!"
    Reviewed June 5, 2026
    Roundtrip • Toronto (YYZ) - Milwaukee (MKE)
    YYZ - MKE • 1 stop MKE - YYZ • 1 stop
    CA $1,110
    CA $1,034
    per traveller
    found 1 day ago
    Kinn Guesthouse Downtown

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

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 $207 per night from Jun 8 to Jun 9
CA $207
CA $244 total
Jun 8 - Jun 9
includes taxes & fees
9.2/10 Wonderful! (1,522 reviews)
"The new interiors design makes it feel like a mini vegas resort. The vibes were great."

Reviewed on Jun 6, 2026

Potawatomi Hotel & Casino
The Pfister Hotel

The Pfister Hotel

4.5 out of 5
424 E Wisconsin Ave Milwaukee WI
The price is CA $308 per night from Jun 21 to Jun 22
CA $308
CA $363 total
Jun 21 - Jun 22
includes taxes & fees
9.6/10 Exceptional! (2,124 reviews)
"The entire staff we encountered were helpful and kind! From checking in, to valet, to the cafe, to room service, we had a great experience with everything."

Reviewed on Jun 6, 2026

The Pfister Hotel
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
The price is CA $147 per night from Jun 28 to Jun 29
CA $147
CA $170 total
Jun 28 - Jun 29
includes taxes & fees
8.4/10 Very Good! (871 reviews)
"Had a great time at the hotel. Definitely my go to when visiting Milwaukee / Brookfield. both pools and gym are well maintained."

Reviewed on Jun 6, 2026

Sheraton Milwaukee Brookfield Hotel
See all 1,238 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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Family Vacations
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Frequently asked questions

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

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

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
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
Thrilling Downtown Scavenger Hunt Game in Milwaukee

Thrilling Downtown Scavenger Hunt Game in Milwaukee

CA $14
per adult
Thrilling Downtown Scavenger Hunt Game 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.