Waukesha County Holidays from NZ$2,874

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Top destinations in Waukesha County

FlightsFlightsHotelsHotels

Milwaukee

Milwaukee

The Latest Waukesha County Holiday Deals

Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Downtown Chicago
Price was NZ$3,399, price is now NZ$2,874 per person
NZ$2,874
per person
17 Aug - 22 Aug
found 13 hours ago
Return flight included
Christchurch (CHC) to Chicago (ORD)
8.4/10 Very Good! (3,935 reviews)
I stayed here for three nights and it was phenomenal! There are so many shops and restaurants within walking distance making this a very convenient spot.

Reviewed on 13 June 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was NZ$4,304, price is now NZ$3,403 per person
NZ$3,403
per person
17 Aug - 22 Aug
found 13 hours ago
Return flight included
Christchurch (CHC) to Chicago (ORD)
9.2/10 Wonderful! (1,325 reviews)
Rooftop Movie theater looked fun during the daytime, but wasn’t committed enough to buy a ticket after sunset. Rooms were fine. Coffee shop was short-staffed the day I was there - to the point I gave up and moved on. The staff I ran into in the hotel from housekeeping to front desk to bell staff were all universally pleasant and helpful. Location was great - convenient to the show I was attending at the Cobra Lounge and to a pretty decent variety of decent looking food options. Don’t miss the Hubbard St viaducts on your morning walk.

Reviewed on 8 June 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was NZ$4,254, price is now NZ$3,378 per person
NZ$3,378
per person
17 Aug - 22 Aug
found 13 hours ago
Return flight included
Christchurch (CHC) to Chicago (ORD)
9.2/10 Wonderful! (491 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 14 June 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was NZ$3,491, price is now NZ$2,924 per person
NZ$2,924
per person
17 Aug - 22 Aug
found 13 hours ago
Return flight included
Christchurch (CHC) to Chicago (ORD)
9.2/10 Wonderful! (1,799 reviews)
Perfect location. Great staff. Room a little outdated especially the bathroom but clean and large

Reviewed on 14 June 2026

Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
Downtown Chicago
Price was NZ$3,710, price is now NZ$3,133 per person
NZ$3,133
per person
17 Aug - 22 Aug
found 13 hours ago
Return flight included
Christchurch (CHC) to Chicago (ORD)
8.8/10 Excellent! (1,008 reviews)
Staff was friendly & welcoming. Room was comfortable. Great location!!

Reviewed on 8 June 2026

Our pick of the best 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 NZ$209 per night from 28 June to 29 June
NZ$209
28 June - 29 June
includes taxes & fees
8.4/10 Very Good! (886 reviews)
"We arrived at 4pm on Friday, the restaurant/bare was to open at 4:30pm. We we waited until 5pm still not open, proceeded to the Market pantry to find the coolers we empty of alcohol, wine and savory snacks. Went and sat in the lobby and the restaurant did open at 5.45pm. Saturday the restaurant didn’t ..."

Reviewed on 14 June 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 NZ$271 per night from 2 July to 3 July
NZ$271
2 July - 3 July
includes taxes & fees
9/10 Wonderful! (1,287 reviews)
"Great location, convenient to all activities that we engaged in. All the amenities were great. When we are in the area again would book again."

Reviewed on 13 June 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 NZ$207 per night from 18 June to 19 June
NZ$207
18 June - 19 June
includes taxes & fees
8.6/10 Excellent! (825 reviews)
"Had a wonderful stay! Staff was very helpful and attentive. Plenty of parking, and great food from the restaurant. Not far from the MKE airport and was very close to the venue in Oconomowoc I attended for an event. Would absolutely stay here again!"

Reviewed on 13 June 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 holiday package cost?
Discover the best of Waukesha County from as low as NZ$2,874. 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.

Stay near popular Waukesha County attractions

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

The Corners of Brookfield

4.4/5 (131 reviews)
You can enjoy retail therapy at The Corners of Brookfield during your stay in Brookfield. Visit 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.