Waukesha County Vacations & Trips from ￥348,788

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    Better together
    Save up to ￥45,448 when you book a flight and hotel together*
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The Latest Waukesha County Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
per person
Aug 1 - Aug 9
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
8.8/10 Excellent! (1,781 reviews)
Enjoyed staying here

Reviewed on Jun 27, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Aug 1 - Aug 9
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,623 reviews)
Pablo, the manager, got our great Chicago stay even better!

Reviewed on Jun 24, 2025

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
per person
Jul 28 - Aug 1
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,123 reviews)
My stay at The Thompson Chicago was excellent. My room was spacious and had a great view of the lake. The floor to ceiling windows provided amazing natural light. Housekeeping came to clean everyday which was most appreciated.The front desk staff was very pleasant and hospitable and answered any questions I had. Will definitely stay here again!

Reviewed on Jun 27, 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
per person
Aug 1 - Aug 9
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (3,353 reviews)
Very comfortable hotel. Very responsive staff.

Reviewed on Jun 25, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
Aug 1 - Aug 9
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.2/10 Wonderful! (1,091 reviews)
Staying at The Emily was a great experience for my first trip to Chicago. The location is great, as it's close to so many attractions and restaurants, including a delicious on-site restaurant, Fora, which I had twice in my three days. The front desk staff was friendly and informative, while the cleaning staff left my room sparkling. The room offered plenty of natural light, a comfortable king bed and a strong air conditioner (which was a necessity during a heat wave). I will definitely be considering The Emily when I take my next trip to Chicago.

Reviewed on Jun 22, 2025

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 ￥11,427 per night from Jul 6 to Jul 7
￥11,427
￥13,199 total
Jul 6 - Jul 7
includes taxes & fees
8.4/10 Very Good! (289 reviews)
"Convenient and clean"

Reviewed on Jun 25, 2025

Sheraton Milwaukee Brookfield Hotel
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 ￥11,861 per night from Jul 21 to Jul 22
￥11,861
￥13,699 total
Jul 21 - Jul 22
includes taxes & fees
8/10 Very Good! (1,111 reviews)
For the $100/night price it was great.
"The pool area is definitely not in good condition… there is no hot tub there looks like it was filled in. Windows behind where it was are really clouded unable to see out, room for pool is just dingy. The hallways had a dirty diaper old food smell but we weren’t there long. The rooms were great except ..."

Reviewed on Jun 26, 2025

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 ￥17,532 per night from Jun 30 to Jul 1
￥17,532
￥20,249 total
Jun 30 - Jul 1
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
"Good"

Reviewed on Jun 25, 2025

Embassy Suites by Hilton Milwaukee Brookfield
See all 2,308 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 ￥348,788. 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.