Waukesha County Vacations & Trips from NT$43,751

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Top destinations in Waukesha County

A calm lake with a boat in the distance, surrounded by trees and a cloudy sky.
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Mukwonago

Mukwonago
A modern architectural structure with a curved roof and glass facade.
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Milwaukee

Milwaukee

The Latest Waukesha County Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was NT$51,283, price is now NT$43,751 per person
NT$43,751
per person
Jan 23 - Jan 26
found 1 hour ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
9.2/10 Wonderful! (1,358 reviews)

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was NT$58,257, price is now NT$46,738 per person
NT$46,738
per person
Jan 23 - Jan 26
found 1 hour ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
9.4/10 Exceptional! (5,555 reviews)
Great location, nice rooms, nice rooftop bar and large breakfast buffet included.

Reviewed on 2026/10/28

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was NT$63,081, price is now NT$53,150 per person
NT$53,150
per person
Jan 23 - Jan 26
found 1 hour ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was NT$56,175, price is now NT$48,342 per person
NT$48,342
per person
Jan 23 - Jan 26
found 1 hour ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
9.2/10 Wonderful! (1,149 reviews)
What a fun and unique stay… a condo where non-sold units are rented. Spotlessly clean, think never lived in (but had been occupied), digital security to maximize safety at all times, located in a hip and vibrant River North neighborhood - lovely restaurants/bars, spas, shopping, etc. On-site parking, staff most helpful (love Joy - the evening auditor). The amenities including gym, rooftop gathering and more….slept like a rock with the bedroom windows open to the balcony….little noise. A perfect stay at a fantastic rate. With Expedia gold membership saved 83%. Check out the space and the Expedia app for bookings!

Reviewed on 2026/10/28

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was NT$52,134, price is now NT$45,036 per person
NT$45,036
per person
Jan 23 - Jan 26
found 1 hour ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
9.4/10 Exceptional! (185 reviews)

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 NT$2,821 per night from Nov 9 to Nov 10
NT$2,821
NT$3,258 total
Nov 9 - Nov 10
includes taxes & fees
Sheraton Milwaukee Brookfield Hotel
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 NT$2,597 per night from Nov 22 to Nov 23
NT$2,597
NT$3,000 total
Nov 22 - Nov 23
includes taxes & fees
AmericInn by Wyndham 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 NT$3,142 per night from Nov 22 to Nov 23
NT$3,142
NT$3,629 total
Nov 22 - Nov 23
includes taxes & fees
Country Inn & Suites by Radisson, Milwaukee West (Brookfield), WI
See all 2,194 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 NT$43,751. 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

The entrance to Veterans Memorial Park with stone archways and flags.

Lac La Belle

9.6/10 (14 reviews)
Commune with nature and explore the great outdoors at Lac La Belle during your travels in Oconomowoc. Visit the shops or attend a sporting event in this relaxing area.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.