Waukesha County Packages (Flight + Hotel)

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    Save up to ฿4,531 when you book a flight and hotel together*
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Top Waukesha County Flight + Hotel Deals

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

Arlo Chicago

4 out of 5
Downtown Chicago
per person
1 Sept - 3 Sept
found 1 day ago
Return flight included
Calgary (YYC) to Chicago (ORD)
9.2/10 Wonderful! (1,785 reviews)
The servers and bartenders at the property were amazing! Gentleman who stored our luggage was polite and extremely attentive!

Reviewed on 16 Jul 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
1 Sept - 3 Sept
found 23 hours ago
Return flight included
Calgary (YYC) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
There was an odd odor. My room was not ready for several hours after check in.

Reviewed on 17 Jul 2025

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
per person
1 Sept - 3 Sept
found 1 day ago
Return flight included
Calgary (YYC) to Chicago (ORD)
8.6/10 Excellent! (1,795 reviews)
I had a great stay. No complaints. The staff was great.

Reviewed on 17 Jul 2025

Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
per person
1 Sept - 3 Sept
found 1 day ago
Return flight included
Calgary (YYC) 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

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
1 Sept - 3 Sept
found 23 hours ago
Return flight included
Calgary (YYC) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
The room is spacious and the bedding is comfortable. The washroom is sparkling clean. The breakfast buffet is an excellent addition to our stay. We all love it.

Reviewed on 18 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 ฿2,721 per night from 11 Aug to 12 Aug
฿2,721
฿3,142 total
11 Aug - 12 Aug
includes taxes & fees
8/10 Very Good! (1,158 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
Fully refundableReserve now, pay when you stay
The price is ฿3,077 per night from 3 Aug to 4 Aug
฿3,077
฿3,554 total
3 Aug - 4 Aug
includes taxes & fees
8.4/10 Very Good! (317 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 ฿4,247 per night from 17 Aug to 18 Aug
฿4,247
฿4,905 total
17 Aug - 18 Aug
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"Very nice hotel with nice rooms and a nice lobby area,close to some stores and restaurants. The breakfast it good,you can order a omelette from a chef. The only downside is the sofas and the chairs from the lobby area need to be steam wash more often. Very good hotel if you are on the area"

Reviewed on 11 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 ฿13,736. 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 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.