Waukesha County Vacations & Trips from ￥302,736

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Top destinations in Waukesha County

FlightsFlightsHotelsHotels

Milwaukee

Milwaukee

The Latest Waukesha County Vacation Packages

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

Arlo Chicago

4 out of 5
Downtown Chicago
Price was ￥396,984, price is now ￥302,736 per person
￥302,736
per person
Aug 3 - Aug 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,129 reviews)
Great staff. Room was small. Good location.

Reviewed on Jun 17, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥417,486, price is now ￥313,106 per person
￥313,106
per person
Aug 5 - Aug 9
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (4,391 reviews)
The rooftop bar was great.

Reviewed on Jun 17, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was ￥441,820, price is now ￥351,874 per person
￥351,874
per person
Aug 5 - Aug 9
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (489 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.

Reviewed on Jun 11, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was ￥417,497, price is now ￥334,064 per person
￥334,064
per person
Aug 5 - Aug 9
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (493 reviews)
If you drive, it’s very close to everything pretty much. It’s clean and nice to stay with family. Parking is a little expensive but that applies to most of Chicago area.

Reviewed on Jun 14, 2026

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was ￥901,730, price is now ￥723,208 per person
￥723,208
per person
Aug 31 - Sep 9
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.8/10 Exceptional! (1,007 reviews)
Excellent and fast service, walking distance to restaurants, shopping, lake, etc.

Reviewed on Jun 7, 2026

Waukesha County Hotel Deals

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 ￥16,989 per night from Jun 28 to Jun 29
￥16,989
￥19,623 total
Jun 28 - Jun 29
includes taxes & fees
8.4/10 Very Good! (896 reviews)
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Reviewed on Jun 18, 2026

Sheraton Milwaukee Brookfield Hotel
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 ￥20,018 per night from Jul 12 to Jul 13
￥20,018
￥23,121 total
Jul 12 - Jul 13
includes taxes & fees
9/10 Wonderful! (1,280 reviews)
"The hotel is in serious need of a refresh. One of the chairs in our room had the faux leather worn off the top of it. Rooms are outdated-bathroom especially needs to be replaced."

Reviewed on Jun 16, 2026

Embassy Suites by Hilton Milwaukee Brookfield
The Ingleside Hotel

The Ingleside Hotel

4 out of 5
2810 Golf Road Pewaukee WI
Fully refundableReserve now, pay when you stay
The price is ￥17,202 per night from Jun 21 to Jun 22
￥17,202
￥19,439 total
Jun 21 - Jun 22
includes taxes & fees
8.6/10 Excellent! (834 reviews)
"The staff were incredibly helpful and friendly. Sarah at the front desk was particularly accommodating and cordial."

Reviewed on Jun 18, 2026

The Ingleside Hotel
See all 2,189 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 ￥302,736. 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.

Stay near popular Waukesha County attractions

Photo by Scott D. Irwin
Open Photo by Scott D. Irwin

The Corners of Brookfield

8.8/5 (131 reviews)
You can browse for the perfect souvenirs at The Corners of Brookfield during your trip to Brookfield. Check out the shops and top-notch restaurants in this family-friendly area.
See properties
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.