Southeast Wisconsin Vacations from ￥301,750

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The Latest Southeast Wisconsin Vacation Packages

Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Downtown Chicago
Price was ￥356,858, price is now ￥301,750 per person
￥301,750
per person
Dec 21 - Dec 28
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (1,009 reviews)

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥443,360, price is now ￥354,362 per person
￥354,362
per person
Dec 21 - Dec 28
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (5,555 reviews)
We really enjoyed our stay at RIU - Chicago. The staff was very nice and professional. The room was clean and the bed slept great. Happy hour on the hotel's rooftop was excellent. The city views are amazing and the drinks were great. The rooftop has heating stations at the tables and around the seating areas that allowed us to enjoy the views on the rooftop outside while staying warm. The rooftop also has an observation window that is cute and exciting! Finally, the location of the hotel is close to all the main attractions and the Magnificent Mile. We would definitely stay at the RIU - Chicago again!

Reviewed on Nov 2, 2026

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Price was ￥395,722, price is now ￥345,301 per person
￥345,301
per person
Dec 21 - Dec 28
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,005 reviews)

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥351,140, price is now ￥307,257 per person
￥307,257
per person
Dec 21 - Dec 28
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (3,148 reviews)

Creekside Grand Lodge

Creekside Grand Lodge

2 out of 5
Save 100% on your flight
Price was ￥4,465,636, price is now ￥3,908,324 per person
￥3,908,324
per person
Dec 5 - Dec 12
found 6 hours ago
Roundtrip flight included
Nagoya (NGO) to Chicago (ORD)
No reviews

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
A river with a city skyline, including a tall building with a pointed roof, and a park with yellow trees.

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

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 ￥15,598 per night from Nov 23 to Nov 24
￥15,598
￥18,390 total
Nov 23 - Nov 24
includes taxes & fees
8.6/10 Excellent! (1,573 reviews)
"Great place to stay. Staff was friendly and helpful. Location is perfect for walking to many different places around the city."

Reviewed on Nov 2, 2026

Hyatt Regency Milwaukee
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 ￥13,708 per night from Nov 9 to Nov 10
￥13,708
￥15,833 total
Nov 9 - Nov 10
includes taxes & fees
Sheraton Milwaukee Brookfield Hotel
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 ￥17,488 per night from Nov 30 to Dec 1
￥17,488
￥20,620 total
Nov 30 - Dec 1
includes taxes & fees
9.6/10 Exceptional! (2,433 reviews)
"Great location, comfortable bed, good snacks"

Reviewed on Nov 2, 2026

Drury Plaza Hotel Milwaukee Downtown
See all 2,439 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.

Stay near popular Southeast Wisconsin 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

Frequently asked questions

How much does a Southeast Wisconsin vacation package cost?
Much less than you might think — from as low as ￥301,750, 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.

Explore a world of travel with Expedia

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