Southeast Wisconsin Vacations from ￥355,796

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The Latest Southeast Wisconsin Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was ￥467,374, price is now ￥355,796 per person
￥355,796
per person
Sep 14 - Sep 18
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (509 reviews)

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was ￥547,898, price is now ￥370,632 per person
￥370,632
per person
Sep 14 - Sep 18
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,041 reviews)

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
Downtown Chicago
Price was ￥675,684, price is now ￥495,208 per person
￥495,208
per person
Oct 8 - Oct 13
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (2,325 reviews)
The hotel is comfortable and well-maintained. It is located at the base of an L train. Stop that whisks passengers to Midway airport in 30 minutes. The location also gives access to Grant Park, State Street and the miracle mile. Rooms are large, comfortable and clean.

Reviewed on Aug 3, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was ￥582,115, price is now ￥428,977 per person
￥428,977
per person
Oct 8 - Oct 13
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (2,606 reviews)

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥591,690, price is now ￥440,253 per person
￥440,253
per person
Oct 8 - Oct 13
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (3,732 reviews)
Amazing friendly staff, great location, and the room was clean.

Reviewed on Aug 3, 2026

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

Harbor Shores on Lake Geneva

Harbor Shores on Lake Geneva

3.5 out of 5
300 Wrigley Dr Lake Geneva WI
Fully refundableReserve now, pay when you stay
The price is ￥25,357 per night from Aug 30 to Aug 31
￥25,357
￥32,270 total
Aug 30 - Aug 31
includes taxes & fees
9.2/10 Wonderful! (1,379 reviews)
"Bathroom wasn’t super clean when we arrived. We did have to throw a toilet paper roll away as it had stuff all over it. Room was nice as it had a fridge and microwave. Easy to check in and out. Close to downtown"

Reviewed on Aug 2, 2026

Harbor Shores on Lake Geneva
AmericInn by Wyndham Brookfield

AmericInn by Wyndham Brookfield

3 out of 5
16865 W Bluemound Rd Brookfield WI
Fully refundableReserve now, pay when you stay
The price is ￥12,608 per night from Aug 9 to Aug 10
￥12,608
￥14,563 total
Aug 9 - Aug 10
includes taxes & fees
8/10 Very Good! (1,450 reviews)
"Not a lot to write about."

Reviewed on Aug 3, 2026

AmericInn by Wyndham Brookfield
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 ￥18,731 per night from Aug 20 to Aug 21
￥18,731
￥21,634 total
Aug 20 - Aug 21
includes taxes & fees
Sheraton Milwaukee Brookfield Hotel
See all 2,468 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 baseball game in a stadium with a person holding a hot dog and a drink.
Photo by Tim Ard
Open Photo by Tim Ard

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 ￥355,796, 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.