Southeast Wisconsin Vacation Packages

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Top Southeast Wisconsin Vacation Deals

Price found within the past 48 hours. Click for updated prices.
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug. 15 - Aug. 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,002 reviews)
Great location and a lovely space.

Reviewed on May 26, 2024

Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 4 - Jul. 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (97 reviews)
Outstanding service and facility.

Reviewed on Jan. 10, 2024

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 4 - Jul. 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (687 reviews)
This is probably the very best location to stay when visiting Chicago. A beautiful old Art Deco building that has been beautifully maintained. We loved staying here. Easy walk to everything.

Reviewed on May 25, 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug. 15 - Aug. 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,190 reviews)
Great view and environment

Reviewed on May 23, 2024

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 4 - Jul. 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,012 reviews)
Maybe the best stay in Chicago. Great room, service and facilities.

Reviewed on May 22, 2024

Where to stay in Southeast Wisconsin

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

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 hotel + flight trips in Downtown Milwaukee

Southeast Wisconsin Hotel Deals

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 $181 per night from May 28 to May 29
CA $181
CA $213 total
includes taxes & fees
May 28 - May 29
9.6/10 Exceptional! (1,664 reviews)
"Staff was very friendly and helpful"

Reviewed on May 25, 2024

Saint Kate - The Arts Hotel
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 $232 per night from Jun. 3 to Jun. 4
CA $232
CA $276 total
includes taxes & fees
Jun 3 - Jun 4
9.4/10 Exceptional! (1,306 reviews)
"You the lobby is under renovation with scaffolding everywhere, detracting from the appreciation. This should have been posted on the website so i could choose to go elsewhere. No discounts for conditions, rooms full price"

Reviewed on May 24, 2024

The Pfister Hotel
Timber Ridge Lodge and Waterpark
Timber Ridge Lodge and Waterpark
3.5 out of 5
7020 Grand Geneva Way, Lake Geneva, WI
Fully refundableReserve now, pay when you stay
The price is CA $218 per night from Jun. 10 to Jun. 11
CA $218
CA $288 total
includes taxes & fees
Jun 10 - Jun 11
8.4/10 Very Good! (2,299 reviews)
"Had a fantastic time with great staff members"

Reviewed on May 23, 2024

Timber Ridge Lodge and Waterpark
See all 2,362 properties in Southeast Wisconsin
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 Southeast Wisconsin vacation package cost?
Much less than you might think — from as low as CA $851, as a matter of fact! By combining hotels, flights and car rentals into your own custom-made vacation package, your getaway to Southeast Wisconsin is just clicks away.
How do I get a cheap travel package to Southeast Wisconsin?
Bundle your flights and hotels, add on extras such as activities, and save with a Southeast Wisconsin vacation package. You won’t just pick up exciting discounts on your adventure — you’ll have lots of choice within your reach too. When you book through Expedia, you can select from more than 550 airlines and 1,000,000 hotels around the globe. Your next big adventure starts right here, right now!
Where should I stay in Southeast Wisconsin?
You’ll fall in love with Milwaukee. Renowned sights, such as Milwaukee Art Museum and American Family Field, will keep you busy in this exciting city.
What are the top hotels in Southeast Wisconsin?
For hotels in Milwaukee with friendly service and comfy beds, you can’t beat Potawatomi Hotel & Casino and Best Western Plus Milwaukee Airport Hotel & Conference Ctr. If you’re visiting Lake Geneva as well, you can look forward to a solid night’s sleep at Mt. Olympus Water & Theme Park Resort or Hilton Milwaukee City Center.
How far in advance should I book my Southeast Wisconsin vacation?
Savvy travelers always book early. Air carriers typically release flight tickets up to 12 months prior to departure, and this is your chance to land some of the lowest prices. Boss just told you to use up your vacation time next month? That’s fine too — Expedia are never short of fantastic deals to send you off on the getaway of your dreams, at a price you can afford.
What does an Expedia Southeast Wisconsin travel package include?
That’s up to you. You can choose from a range of Southeast Wisconsin bundles, such as a flight, hotel and rental car. You can also book a flight and a hotel, or a rental car with a flight. Once you’ve made your booking, you can add on the fun stuff like experiences and activities. Whatever your Southeast Wisconsin trip looks like, get set to save!
What should I know before booking a Southeast Wisconsin travel package?
When you book your hotels, flights and car rentals together, you’ll land awesome discounts. Whether you’re organizing a rural escape in a cottage or want to stay in a ritzy city hotel, Expedia can make it happen for less.
Can I choose my airline with a Southeast Wisconsin Expedia vacation package?
Definitely. Expedia has over 550 partner airlines to select from around the world. With so much choice, finding the right carrier to take you to Southeast Wisconsin will be a breeze.
If I'm not able to travel, can I cancel my Southeast Wisconsin vacation package?
It is possible to cancel your Southeast Wisconsin booking if your travel plans have been upended. Whether you’ll be charged a fee or not depends on your hotel, airline or car rental company. It may be possible to change or cancel your booking free of charge if you booked in the last 24 hours. Visit our Customer Service Portal to learn more.

Discover the most popular places to visit in Southeast Wisconsin

Image for Six Flags Great America

Six Flags Great America

4.5/5(5 reviews)

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America
Image for Harley-Davidson Museum

Harley-Davidson Museum

5/5(13 reviews)

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
Image for Milwaukee County Zoo

Milwaukee County Zoo

5/5(2 reviews)

This sprawling animal park houses a wide array of exotic wildlife, and is acclaimed for its conservation programs and educational resources.

Milwaukee County Zoo

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.