Wisconsin Vacations & Trips from ￥90,622

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The Latest Wisconsin Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was ￥145,090, price is now ￥90,622 per person
￥90,622
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Healthy breakfast and very clean hotel with friendly staff.

Reviewed on Oct 10, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was ￥226,526, price is now ￥148,535 per person
￥148,535
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
The best hotel in chicago

Reviewed on Oct 11, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was ￥412,972, price is now ￥288,140 per person
￥288,140
per person
Dec 23 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
I loved the hotel, however I would request an inside room next time. It was extremely noisy outside.

Reviewed on Oct 11, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was ￥439,202, price is now ￥308,904 per person
￥308,904
per person
Dec 23 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9/10 Wonderful! (352 reviews)
Friendly staff and great amenities

Reviewed on Oct 10, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was ￥370,415, price is now ￥270,296 per person
￥270,296
per person
Dec 23 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.2/10 Wonderful! (291 reviews)
Food price was high but everything was fine

Reviewed on Oct 4, 2025

Where to stay in Wisconsin

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

Wisconsin Hotel Deals

The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

3.5 out of 5
1 W Dayton St, Madison, WI
Fully refundableReserve now, pay when you stay
The price is ￥22,996 per night from Oct 21 to Oct 22
￥22,996
￥26,560 total
Oct 21 - Oct 22
includes taxes & fees
9.4/10 Exceptional! (3,177 reviews)
"Didn’t workout."

Reviewed on Oct 6, 2025

The Madison Concourse Hotel and Governor's Club
Baymont by Wyndham Madison West/Middleton WI West

Baymont by Wyndham Madison West/Middleton WI West

2.5 out of 5
8102 Excelsior Dr, Madison, WI
Fully refundableReserve now, pay when you stay
The price is ￥10,795 per night from Nov 11 to Nov 12
￥10,795
￥12,468 total
Nov 11 - Nov 12
includes taxes & fees
8/10 Very Good! (1,007 reviews)
"Over all a good stay and will be booking again, hopefully the hot tub will be up and running for the next stay"

Reviewed on Oct 5, 2025

Baymont by Wyndham Madison West/Middleton WI West
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 ￥21,361 per night from Nov 2 to Nov 3
￥21,361
￥29,558 total
Nov 2 - Nov 3
includes taxes & fees
8.6/10 Excellent! (3,007 reviews)
"Clean, everyone was friendly and happy to help. Waterpark was well staffed, clean and safe. Food was good we had the pizza. Arcade was fun and parking was easy. Rooms were clean and well kept and showed had great pressure. Overall a good experience"

Reviewed on Oct 11, 2025

Timber Ridge Lodge and Waterpark
See all 15,737 properties in 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 Wisconsin vacation package cost?
Starting from as low as ￥90,622, a package is your portal to low-cost travel. Custom make your Wisconsin adventure by choosing from our extensive range of flights, hotels and rental cars.
How do I get a cheap travel package to Wisconsin?
Bundling your flight and hotel with Expedia won't just save precious time — it'll save you cash too. A Wisconsin vacation package makes it easy to organize your dream adventure. With more than 550 airlines throughout the world to choose from, finding convenient flights that fit your busy schedule won't be an issue. Not only that, we've got over 1,000,000 properties globally to select from. Talk about choice! No matter who you are, Expedia puts the world within your reach.
Where should I stay in Wisconsin?
Milwaukee is a fantastic place to include in your itinerary. It's where you'll find impressive sights such as Milwaukee Art Museum and American Family Field. Madison also attracts many jetsetters eager to explore some of the best attractions in Wisconsin. Some of the best are University of Wisconsin-Madison and Camp Randall Stadium.
What are the top hotels in Wisconsin?
Potawatomi Hotel & Casino and Best Western Plus Milwaukee Airport Hotel & Conference Ctr know how to make their guests feel at home in Milwaukee. If your itinerary also includes Wisconsin Dells, take a look at Inn of the Pines and Silver Spruce Resort. Both are popular with travelers.
How far in advance should I book my Wisconsin vacation?
Savvy travelers will likely want to reserve their seats as early as possible. You can normally compare international fares on Expedia up to a year before your intended flight. If you're booking at the last minute, fear not. Low prices occasionally become available just weeks before departure dates.
What does an Expedia Wisconsin travel package include?
Expedia has all you need to arrange your Wisconsin getaway, but what your package looks like is totally up to you. Choose from a combination of hotels, flights and rental cars. Searching for some activities to fill in your time? Once you've made your booking, you can add them on too. No matter your style or budget, there's a package deal to match your needs.
What should I know before booking a Wisconsin travel package?
Discover deals to match your budget with an Expedia package. Flights, hotels, rental cars — we have everything you need to plan your break. You'll save a tidy sum just for bundling your bookings. Whether you're taking off on a ski trip or sunning yourself on a warm beach, your ideal vacation is only a few clicks away.
Can I choose my airline with a Wisconsin Expedia vacation package?
Yes, you sure can. We have more than 550 partner airlines globally, so go with the carrier that suits your needs.
If I'm not able to travel, can I cancel my Wisconsin vacation package?
Certainly, and we'll help you every step of the way. You may be able to cancel and rebook your Wisconsin vacation package for free if you booked in the last 24 hours. But you may incur a fee from your airline, hotel or car rental company if your booking is older than that. If life gets in the way of your vacation, look up our Customer Service Portal for more information.

Discover the most popular places to visit in Wisconsin

Cool street art in Madison, Wisconsin

University of Wisconsin-Madison

Enjoy the collegiate vibe around University of Wisconsin-Madison, a top college in Madison. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

University of Wisconsin-Madison
Mt. Olympus Water and Theme Park

Mt. Olympus Water and Theme Park

Enjoy the rides and games at Mt. Olympus Water and Theme Park and see why this is a favorite amusement park in Wisconsin Dells. Stroll along the area's lakeside or experience its entertainment choices.

Mt. Olympus Water and Theme Park
Harley-Davidson Museum showing interior views

Harley-Davidson Museum

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

What to do in Wisconsin

Grohmann Museum at Milwaukee School of Engineering

Skip the Line: Museum Admission Ticket - Grohmann Museum

￥732
per adult
Skip the Line: Museum Admission Ticket - Grohmann Museum
Hearthstone is the first house in the world powered by a central hydroelectric dynamo based on the Edison system.

Hearthstone Historic House Museum Admission Ticket

￥1,758
per adult
100% of travellers recommend
Hearthstone Historic House Museum Admission Ticket
360o Barcelona SkyWalk: Old Town Walking, Helicopter flight & Boat Ride

360o Barcelona SkyWalk: Old Town Walking, Helicopter flight & Boat Ride

￥28,679
per adult
92% of travellers recommend
360o Barcelona SkyWalk: Old Town Walking, Helicopter flight & Boat Ride
See all activities in Wisconsin
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.