Southeast Wisconsin Vacations from ￥337,270

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The Latest Southeast Wisconsin Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
per person
Jul 1 - Jul 4
found 1 day ago
Roundtrip flight included
Tokyo (HND) to Chicago (ORD)
8.8/10 Excellent! (1,610 reviews)
Beautiful place, great location, parking nearby.

Reviewed on Apr 29, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Jul 1 - Jul 4
found 1 day ago
Roundtrip flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,546 reviews)
Excellent experience!

Reviewed on Apr 28, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Jul 1 - Jul 4
found 1 day ago
Roundtrip flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,605 reviews)
TV did not work. Was told that it was a problem with the system for everyone and would be fixed in 10 minutes. An hour later I called again and was told the engineer would come to our room next. The engineer never came. No follow up from anyone else. The TV did not work until the next day.

Reviewed on Apr 29, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
Jul 1 - Jul 4
found 1 day ago
Roundtrip flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Gorgeous views, great in room dining, staff were very nice

Reviewed on Apr 28, 2025

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
per person
Jul 1 - Jul 4
found 1 day ago
Roundtrip flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (1,444 reviews)
The hotel clerk who welcomed us upon checking in was the most gracious!

Reviewed on Apr 24, 2025

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 hotels in Downtown Milwaukee

Find the Best Southeast Wisconsin Vacation Packages

Southeast Wisconsin Hotel Deals

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 ￥15,712 per night from May 4 to May 5
￥15,712
￥18,522 total
includes taxes & fees
May 4 - May 5
9.6/10 Exceptional! (1,700 reviews)
Great spot to stay
"Great hotel. Everything was pretty well perfect for our stay, great location, great staff."

Reviewed on Apr 27, 2025

Drury Plaza Hotel Milwaukee Downtown
Crowne Plaza Milwaukee South by IHG
Crowne Plaza Milwaukee South by IHG
3.5 out of 5
6401 S 13th Street, Milwaukee, WI
Fully refundable
The price is ￥11,234 per night from May 4 to May 5
￥11,234
￥13,244 total
includes taxes & fees
May 4 - May 5
8/10 Very Good! (1,004 reviews)
"Staff are amazing. New management sucks!"

Reviewed on Apr 26, 2025

Crowne Plaza Milwaukee South by IHG
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 ￥14,590 per night from May 28 to May 29
￥14,590
￥21,669 total
includes taxes & fees
May 28 - May 29
8.6/10 Excellent! (2,795 reviews)
"Property is a win for our family. Close to home, great Waterpark, rooms in great conditions and more!"

Reviewed on Apr 26, 2025

Timber Ridge Lodge and Waterpark
See all 2,495 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.

Frequently asked questions

How much does a Southeast Wisconsin vacation package cost?
Much less than you might think — from as low as ￥337,270, 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

Harley-Davidson Museum showing interior views

Harley-Davidson Museum

4.5/5(337 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
Milwaukee County Zoo featuring interior views and zoo animals as well as a small group of people

Milwaukee County Zoo

4.5/5(217 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
Milwaukee Art Museum

Milwaukee Art Museum

4.5/5(400 reviews)

Peruse a vast collection of classic European and American art in this gallery that is housed in a striking modern building.

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