Waukesha County Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Top destinations in Waukesha County

Milwaukee Art Museum featuring modern architecture and art
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Milwaukee

Milwaukee

Waukesha County Flight & Hotel Packages

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

Hilton Chicago

4 out of 5
Downtown Chicago
per person
23 Aug - 30 Aug
found 1 day ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
8.4/10 Very Good! (1,986 reviews)
For a four star hotel in chicago it is very pricy only good for location as the amenities and extras are what you gt in a 3 star hotel outside of the city. The carpet is dated and dusty, the bathroom was clean and more modern than expected, but it is not as expected.

Reviewed on 16 Jul, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
23 Aug - 30 Aug
found 1 day ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Beautiful and upscale property

Reviewed on 17 Jul, 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
per person
23 Aug - 30 Aug
found 1 day ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)
The hotel staff were very pleasant, the room was clean, and the hotel was located in a convenient area.

Reviewed on 17 Jul, 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
per person
23 Aug - 30 Aug
found 1 day ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
9/10 Wonderful! (1,000 reviews)
I loved this hotel. It was absolutely beautiful!

Reviewed on 17 Jul, 2025

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
per person
23 Aug - 30 Aug
found 1 day ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
Glad of the location service was excellent. Have no complaints.

Reviewed on 11 Jul, 2025

Top hotels in Waukesha County

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 S$124 per night from 11 Aug to 12 Aug
S$124
11 Aug - 12 Aug
includes taxes & fees
8/10 Very Good! (1,167 reviews)
"Nice place to stay. Reasonable drive to downtown and in a nice area with lots of shopping and restaurants!"

Reviewed on 14 Jul, 2025

Sonesta Select Milwaukee Brookfield
Sheraton Milwaukee Brookfield Hotel

Sheraton Milwaukee Brookfield Hotel

3.5 out of 5
375 S Moorland Rd, Brookfield, WI
The price is S$141 per night from 3 Aug to 4 Aug
S$141
3 Aug - 4 Aug
includes taxes & fees
8.4/10 Very Good! (319 reviews)
"Place is accessible to the highway and restaurants, the room was very clean. I utilized the fitness room twice it was quiet no one there so I was able to do my workout on my own. I was able to get food from the lounge area and it was very tasty."

Reviewed on 13 Jul, 2025

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 S$195 per night from 10 Aug to 11 Aug
S$195
10 Aug - 11 Aug
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"Everything was great no dislikes"

Reviewed on 16 Jul, 2025

Embassy Suites by Hilton Milwaukee Brookfield
See all 2,329 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 holiday package cost?
Discover the best of Waukesha County from as low as S$1,967. 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 holiday 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 holiday 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 holiday?
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 travellers 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 holiday 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 holiday packages today.
Can I choose my airline with a Waukesha County Expedia holiday package?
Yes — that's the beauty of an Expedia holiday 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 holiday package?
Don't worry if you're rethinking your Waukesha County holiday 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.