Waukesha County Vacations & Trips from ￥271,029

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Top destinations in Waukesha County

Milwaukee Art Museum featuring art and modern architecture
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Milwaukee

Milwaukee

The Latest Waukesha County Vacation Packages

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

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was ￥309,748, price is now ￥271,029 per person
￥271,029
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Clean room and amenities

Reviewed on Jan 8, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥400,704, price is now ￥319,797 per person
￥319,797
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Exceptional service, great location, beautiful hotel

Reviewed on Jan 20, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was ￥337,890, price is now ￥285,200 per person
￥285,200
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Property was clean, welcoming, pet friendly

Reviewed on Jan 18, 2026

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Price was ￥403,904, price is now ￥341,974 per person
￥341,974
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
Yes didn’t know you get free breakfast

Reviewed on Jan 4, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was ￥314,537, price is now ￥275,702 per person
￥275,702
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Everything about this hotel is special. Great staff- awesome restaurant/bar. Location is perfect. This hotel is my destination every time I come to the city. Which is quite often.

Reviewed on Jan 20, 2026

Waukesha County Hotel Deals

Sonesta Select Milwaukee Brookfield

Sonesta Select Milwaukee Brookfield

3 out of 5
16865 W Bluemound Rd Brookfield WI
Fully refundableReserve now, pay when you stay
The price is ￥11,295 per night from Jan 22 to Jan 23
￥11,295
￥13,046 total
Jan 22 - Jan 23
includes taxes & fees
8/10 Very Good! (1,376 reviews)
Lacking variety

Reviewed on Jan 16, 2026

Sonesta Select Milwaukee Brookfield
Embassy Suites by Hilton Milwaukee Brookfield

Embassy Suites by Hilton Milwaukee Brookfield

3.5 out of 5
1200 S Moorland Rd Brookfield WI
Fully refundableReserve now, pay when you stay
The price is ￥16,085 per night from Jan 28 to Jan 29
￥16,085
￥18,578 total
Jan 28 - Jan 29
includes taxes & fees
8.8/10 Excellent! (1,068 reviews)
I slept in so I went to IHOP across the street.

Reviewed on Jan 14, 2026

Embassy Suites by Hilton Milwaukee Brookfield
Country Inn & Suites by Radisson, Milwaukee West (Brookfield), WI

Country Inn & Suites by Radisson, Milwaukee West (Brookfield), WI

3 out of 5
1250 S Moorland Rd Brookfield WI
Fully refundable
The price is ￥14,656 per night from Jan 28 to Jan 29
￥14,656
￥16,928 total
Jan 28 - Jan 29
includes taxes & fees
8.6/10 Excellent! (1,287 reviews)
Very nice room good food nice service

Reviewed on Jan 16, 2026

Country Inn & Suites by Radisson, Milwaukee West (Brookfield), WI
See all 2,114 properties in Waukesha County
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 Waukesha County vacation package cost?
Discover the best of Waukesha County from as low as ￥271,029. We offer a wonderful selection of hotels, flights and rental cars to suit your travel style. You can score even better deals when you add a couple of tours or activities to your vacation package.
How do I get a cheap travel package to Waukesha County?
Combine your flight and hotel bookings, add extras such as activities, and save with a Waukesha County vacation package. You won't just pick up awesome discounts on your escape — you'll have plenty of choice too. When you book with Expedia, you can select from more than 550 airlines and 1,000,000 properties throughout the world. Your next big adventure begins right here, right now!
What are the top hotels in Waukesha County?
For properties in Oconomowoc with comfy beds and friendly service, look up Mt. Olympus Water & Theme Park Resort and The Madison Concourse Hotel and Governors Club. If you plan to visit Mukwonago as well, you can look forward to a wonderful night's sleep at Embassy Suites by Hilton Milwaukee Brookfield or La Quinta Inn & Suites by Wyndham Milwaukee SW New Berlin.
How far in advance should I book my Waukesha County vacation?
It depends on the airline, but it's usually possible to browse through international airfares on Expedia up to a year in advance. While it's advisable to book ahead of time, lucky travelers will occasionally score a cheaper ticket just weeks before the date of departure.
What does an Expedia Waukesha County travel package include?
That mostly depends on you. You can choose from a range of Waukesha County packages, 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 the fun stuff like activities and tours. Whatever your ideal Waukesha County vacation looks like, you'll save!
What should I know before booking a Waukesha County travel package?
You'll enjoy amazing savings when you combine your hotels, flights and rental cars into a package. Not just that, booking everything in one place makes trip planning easier. So why waste your money or time? Whether you're putting together a fancy romantic getaway or a low-cost family road trip, browse our vacation packages today.
Can I choose my airline with a Waukesha County Expedia vacation package?
Yes — that's the beauty of an Expedia vacation package. You can pick and choose your flights, hotels and more. We have access to more than 550 partner airlines all over the world, so you have options galore when arranging your Waukesha County adventure.
If I'm not able to travel, can I cancel my Waukesha County vacation package?
Don't worry if you're rethinking your Waukesha County vacation package — you can cancel or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur charges from your airline, hotel or car rental company. We know life can sometimes throw you a curveball, so look up our Customer Service Portal if that happens. When you're ready to make changes, we're ready to help.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.