Milwaukee County 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

Top Milwaukee County Vacation Deals

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 CA $1,245, price is now CA $969 per person
CA $969
per person
Jan 20 - Jan 24
found 7 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Milwaukee (MKE)
9.4/10 Exceptional! (1,000 reviews)

Kinn Guesthouse Downtown

Kinn Guesthouse Downtown

4.5 out of 5
Downtown Milwaukee
Price was CA $1,594, price is now CA $1,239 per person
CA $1,239
per person
Jan 20 - Jan 24
found 7 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Milwaukee (MKE)
9.4/10 Exceptional! (444 reviews)

The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
Price was CA $1,303, price is now CA $1,064 per person
CA $1,064
per person
Jan 20 - Jan 24
found 7 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Milwaukee (MKE)
9.2/10 Wonderful! (1,378 reviews)

County Clare Irish Hotel & Pub

County Clare Irish Hotel & Pub

2.5 out of 5
Downtown Milwaukee
Price was CA $1,190, price is now CA $982 per person
CA $982
per person
Jan 20 - Jan 24
found 7 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Milwaukee (MKE)
9.6/10 Exceptional! (1,001 reviews)

Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Downtown Milwaukee
Price was CA $1,558, price is now CA $1,291 per person
CA $1,291
per person
Jan 20 - Jan 24
found 7 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Milwaukee (MKE)
9.8/10 Exceptional! (2,742 reviews)

Milwaukee County 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
The price is CA $113 per night from Nov 23 to Nov 24
CA $113
CA $133 total
Nov 23 - Nov 24
includes taxes & fees
Hyatt Regency Milwaukee
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
The price is CA $158 per night from Dec 14 to Dec 15
CA $158
CA $187 total
Dec 14 - Dec 15
includes taxes & fees
Drury Plaza Hotel Milwaukee Downtown
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 $385 per night from Dec 14 to Dec 15
CA $385
CA $454 total
Dec 14 - Dec 15
includes taxes & fees
9.6/10 Exceptional! (2,299 reviews)
"Perfect stay outside of not having internet."

Reviewed on Nov 13, 2026

The Pfister Hotel
See all 960 properties in Milwaukee County
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 Milwaukee County vacation package cost?
Less than you might think — from as low as CA $969, in fact! By bundling hotels, flights and car rentals into a custom-made package, your Milwaukee County escape is just a few clicks away.
How do I get a cheap travel package to Milwaukee County?
Combine your flight and hotel bookings, add on extras such as a rental car or activities, and save with a Milwaukee County vacation package. You won't just pick up superb discounts on your escape — you'll have a world of choice within your reach too. When you book through Expedia, you can select from more than 550 partner airlines and 1,000,000 hotels worldwide. Your next grand adventure starts right here, right now!
How far in advance should I book my Milwaukee County vacation?
You'll be rewarded with the widest variety and the lowest prices by booking your vacation to Milwaukee County early. Air carriers typically publish flight tickets anywhere up to a year in advance, so reserve your spot as soon as you can. That said, Expedia is dedicated to giving you the best bargains around, so it's never a bad time to book your dream vacation!
What does an Expedia Milwaukee County travel package include?
From flights and hotels to car rentals, Expedia can help you craft a Milwaukee County package that's perfect for you. Heading away for a while? Give some thought to a flight, hotel and rental car bundle. If you can only squeeze in a quick getaway, an airfare and hotel deal may suit you better. Activities can also be added after you've booked. Our travel packages make it a breeze to plan and save.
What should I know before booking a Milwaukee County travel package?
Booking all the parts of your trip together is an excellent way to save. Bundle your car rentals, airfares and hotels into a handy package. But hotels aren't your only option. Expedia has all kinds of properties, including vacation rentals such as beach villas and city residences. You've got choices galore!
Can I choose my airline with a Milwaukee County Expedia vacation package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines globally. Our vacation packages give you the freedom to take your pick of available flights, hotels and activities that suit you.
If I'm not able to travel, can I cancel my Milwaukee County vacation package?
If your travel plans in Milwaukee County have changed, it's a relief to know that you can cancel or amend your booking. If you made your booking within the last 24 hours, you may be eligible for a refund. If your booking is older than that, your airline, hotel or car rental company may charge a fee. To find out more, check our Customer Service Portal.

Stay near popular Milwaukee County attractions

A sign for Miller Park, home of the Milwaukee Brewers, with a baseball and stars.
Photo by trenton.badillo
Open Photo by trenton.badillo

American Family Field

9.0/10 (2,832 reviews)
Catch an event at American Family Field during your trip to Milwaukee. Attend a baseball game or simply enjoy the lively breweries while you're in the area.
See properties

What to do in Milwaukee County

Milwaukee Food Tour with 5 Local Favorites Tastings & Secret Dish

Milwaukee Food Tour with 5 Local Favorites Tastings & Secret Dish

CA $144
per adult
Milwaukee Food Tour with 5 Local Favorites Tastings & Secret Dish
Milwaukee: Original Ghost Tour

Milwaukee: Original Ghost Tour

CA $69
per adult
Milwaukee: Original Ghost Tour
Milwaukee Historic Downtown Self Guided Walking Tour

Milwaukee Historic Downtown Self Guided Walking Tour

CA $14
per adult
Milwaukee Historic Downtown Self Guided Walking Tour
See all activities in Milwaukee County
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.