Downtown Milwaukee Vacation Packages

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Top Holiday Package Deals in Downtown Milwaukee

Price found within the past 48 hours. Click for updated prices.
County Clare Irish Hotel & Pub

County Clare Irish Hotel & Pub

2.5 out of 5
Downtown Milwaukee
Price was CA $1,031, price is now CA $978 per person
CA $978
per person
Jun 23 - Jun 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
9.6/10 Exceptional! (1,001 reviews)
The hotel is in a great location. Cute atmosphere and has a bar for a nightcap before heading to bed. The front desk helped assure that I had a room waiting after I cancelled and re-scheduled rooms. We arrived at the hotel at midnight and we were assisted with getting room keys by cleaning staff and bar keepers. Very nice cozy place.

Reviewed on May 8, 2026

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
Price was CA $1,338, price is now CA $1,149 per person
CA $1,149
per person
Jun 23 - Jun 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
9.6/10 Exceptional! (2,095 reviews)
I would have liked a shower cap The room was clean and large Bedsheets and pillows comfortable Room was quiet love the night lights

Reviewed on May 10, 2026

The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
Price was CA $1,372, price is now CA $1,268 per person
CA $1,268
per person
Jun 23 - Jun 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
9.2/10 Wonderful! (1,099 reviews)
This hotel hosts an event during the weekend of the Kentucky Derby. Unless you are attending the event- I would avoid the hotel during this weekend. Many hotel amenities are adjusted to cater to those participating in the Derby event- it’s not beneficial for guests who are not.

Reviewed on May 10, 2026

Kinn Guesthouse Bay View

Kinn Guesthouse Bay View

4.5 out of 5
Bay View
Price was CA $1,271, price is now CA $1,196 per person
CA $1,196
per person
Jun 23 - Jun 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
9.4/10 Exceptional! (459 reviews)
Love the decor. Felt like home! Walking distance to coffee & dinner places was great!

Reviewed on May 8, 2026

Kinn Guesthouse Downtown

Kinn Guesthouse Downtown

4.5 out of 5
Downtown Milwaukee
Price was CA $1,303, price is now CA $1,237 per person
CA $1,237
per person
Jun 23 - Jun 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
9.4/10 Exceptional! (348 reviews)
It's a fabulous old building converted into a great place to stay. High ceilings and stylish design everywhere made it a very comfortable and cosy place to stay. The bed was amazingly comfortable. It's in a great location as well! I plan to stay here again when I'm back in Milwaukee!!

Reviewed on May 5, 2026

Where to stay in Downtown Milwaukee

Find the best Downtown Milwaukee areas and neighborhoods for the activities you enjoy most. Learn more about Downtown Milwaukee
96144781

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.

Find hotels in Wauwatosa

Downtown Milwaukee 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 $233 per night from May 31 to Jun 1
CA $233
CA $274 total
May 31 - Jun 1
includes taxes & fees
9.6/10 Exceptional! (2,109 reviews)
I feel like royalty when I stay at this beautiful, historic hotel.

Reviewed on May 10, 2026

The Pfister Hotel
Drury Plaza Hotel Milwaukee Downtown

Drury Plaza Hotel Milwaukee Downtown

3 out of 5
700 N. Water Street Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is CA $178 per night from May 25 to May 26
CA $178
CA $210 total
May 25 - May 26
includes taxes & fees
9.6/10 Exceptional! (2,209 reviews)
Loved this place will book again!

Reviewed on May 11, 2026

Drury Plaza Hotel Milwaukee Downtown
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 $215 per night from May 17 to May 18
CA $215
CA $254 total
May 17 - May 18
includes taxes & fees
9.8/10 Exceptional! (2,649 reviews)
This would be a 5 star rating- as we always love St Kate’s. This time however we used the pullout bed and found a sock and underwear.

Reviewed on May 10, 2026

Saint Kate - The Arts Hotel
See all 407 properties in Downtown Milwaukee
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 Downtown Milwaukee vacation package cost?
Our Downtown Milwaukee packages, which start from just CA $978, are an awesome way to save big bucks. Pick and choose your preferred flights, hotels and rental cars to create your dream itinerary.
How do I get a cheap travel package to Downtown Milwaukee?
Our Downtown Milwaukee vacation packages offer plenty of savings for the savvy globetrotter. For the best deals, simply bundle your flights, hotels and extras (such as activities) into one neat package. But great bargains are only the start of your next awesome adventure. When you book with Expedia, and you'll have over 550 air carriers and 1,000,000 hotel options all over the world to pick from. No matter your style or budget, there's a package here just for you.
Where should I stay in Downtown Milwaukee?
A trip to Downtown Milwaukee isn't complete until you've seen Milwaukee Art Museum and American Family Field. Book a hotel right nearby so you can easily access these awesome sights.
What are the top hotels in Downtown Milwaukee?
If this will be your first time in Downtown Milwaukee, make a reservation at Tru By Hilton Milwaukee Downtown, WI or Home2 Suites by Hilton Milwaukee Downtown. Both hotels have good amenities and are favorites among lots of travelers.
How far in advance should I book my Downtown Milwaukee vacation?
It can be hard to know exactly when the best time is to book your trip to Downtown Milwaukee. But usually the earlier you book, the more affordable the prices. In some cases, you can book your flights and hotels up to a year prior to departure. If you're hoping for a last-minute getaway, no need to panic! There are fabulous bargains advertised on Expedia every day.
What does an Expedia Downtown Milwaukee travel package include?
Select from any combination of hotels, rental cars and flights. Once you've made your booking, you can add the fun stuff like experiences and tours. Want to pick your fare class? That's easy to do too. The choice is all yours when it comes to crafting your perfect Downtown Milwaukee escape.
What should I know before booking a Downtown Milwaukee travel package?
Find deals that suit your budget with an Expedia package. Airfares, hotels, rental cars — we have them all. You'll save a packet just for bundling your bookings. Whether you're embarking on an adventure in the snow or sipping cocktails on a beach, your dream vacation is only clicks away.
Can I choose my airline with a Downtown Milwaukee Expedia vacation package?
Yes, definitely. Expedia has more than 550 airline partners to select from worldwide. With such a huge range of choice, finding the right carrier to take you to Downtown Milwaukee will be a breeze.
If I'm not able to travel, can I cancel my Downtown Milwaukee vacation package?
Don't stress if you're rethinking your Downtown Milwaukee 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 for free. However, bookings made more than 24 hours ago may incur a fee from your airline, hotel or car rental company. We know life can occasionally throw a spanner in the travel works, so look up 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 Downtown Milwaukee

Milwaukee City Hall

Milwaukee City Hall

Explore this Milwaukee landmark on an informative tour or simply appreciate its ornate Flemish Renaissance Revival architecture from the forecourt park.

Milwaukee City Hall

Things to do

Skip the Line: Museum Admission Ticket - Grohmann Museum

Skip the Line: Museum Admission Ticket - Grohmann Museum

CA $7
per adult
Skip the Line: Museum Admission Ticket - Grohmann Museum
Milwaukee Morbid Mirrorlight Ghost Tours

Milwaukee Morbid Mirrorlight Ghost Tours

CA $44
per adult
Milwaukee Morbid Mirrorlight Ghost Tours
Small Group Kayak Tour of Skyline in Milwaukee

Small Group Kayak Tour of Skyline in Milwaukee

CA $114
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.