Waukesha County Holidays

Photo by Amy Cristine

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Top destinations in Waukesha County

Milwaukee Art Museum which includes modern architecture and art
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Milwaukee

Milwaukee

Top Flight + Hotel Deals in Waukesha County

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was €1,123, price is now €814 per person
€814
per person
14 Mar - 21 Mar
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
8.2/10 Very Good! (2,365 reviews)
The room was amazing and the customer service was great!

Reviewed on 28 Dec 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was €1,424, price is now €914 per person
€914
per person
14 Mar - 21 Mar
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Jasmine was courteous and friendly, made our check in process smooth. Clean rooms and the breakfast was amazing. I definitely recommend staying here.

Reviewed on 31 Dec 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was €1,395, price is now €960 per person
€960
per person
14 Mar - 21 Mar
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Everything was great!

Reviewed on 29 Dec 2025

Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Price was €1,299, price is now €946 per person
€946
per person
14 Mar - 21 Mar
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
8.4/10 Very Good! (2,301 reviews)
Best option for us while attending an event at McCormick place, with ability to park in public parking that is cheaper than the hotel parking!

Reviewed on 30 Dec 2025

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Price was €1,513, price is now €1,118 per person
€1,118
per person
14 Mar - 21 Mar
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
8.2/10 Very Good! (2,158 reviews)
Staff was excellent, roim was nice

Reviewed on 30 Dec 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 €73 per night from 11 Jan to 12 Jan
€73
11 Jan - 12 Jan 2026
includes taxes & fees
8/10 Very Good! (1,370 reviews)
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Reviewed on 19 Dec 2025

Sonesta Select Milwaukee Brookfield
The Ingleside Hotel

The Ingleside Hotel

4 out of 5
2810 Golf Road Pewaukee WI
The price is €103 per night from 5 Jan to 6 Jan
€103
5 Jan - 6 Jan 2026
includes taxes & fees
8.4/10 Very Good! (760 reviews)
Easy parking and a room was very clean. The pool was nice, although we didn’t use it. Staff was super helpful and very welcoming. And the hotel restaurant had great food and the drinks were not too strong.

Reviewed on 28 Dec 2025

The Ingleside Hotel
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 €91 per night from 13 Jan to 14 Jan
€91
13 Jan - 14 Jan 2026
includes taxes & fees
8.6/10 Excellent! (1,259 reviews)
Great experience all around!

Reviewed on 26 Dec 2025

Country Inn & Suites by Radisson, Milwaukee West (Brookfield), WI
See all 2,145 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 €814. 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.