
Waukesha County Vacations & Trips from $242
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Your Waukesha County Vacation
Make organizing your next big adventure quick and easy with a Waukesha County vacation package. Whether it's history, nature or something else that lures you to this destination, our packages will help you discover it all. Two of the top cities to check out during your trip to Waukesha County are Oconomowoc and Mukwonago. When you're ready to stop dreaming and start discovering, Expedia will help turn your Waukesha County vacation into a reality.
Top destinations in Waukesha County
The Latest Waukesha County Vacation Packages
Price found within the past 48 hours. Click for updated prices.

Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $399, price is now $242 per person
$242
per person
Feb 20 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Staff was friendly and outgoing throughout our 2 night stay. Roome were very clean, spacious with floor to ceiling windows and large walk-in showers. Bottle of wine upon check-in.
Reviewed on Nov 25, 2025

Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $531, price is now $303 per person
$303
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Room was spotless, all the kitchen amenities were provided such as a Nespresso machine with refills, electric kettle, dishes, utensils, pots, and pans. The refrigerator has a water dispenser inside full-size freezer microwave dishwasher. They provide dishwashing detergent and dish soap. Paper towels. Stackable washer and dryer they supply a single sample of laundry detergent to do laundry then you’re on your own. Aldi is on the first floor so if you need anything grocery is available. there is a café attached to the building. Workout area is immaculately cleaned every day. There is a game room a large area to watch TV. we did not bring our pet, but there is an area on the rooftop for pets to run around and there’s green space down below. A full basketball court and an area for children to play. it was winter so the pool and hot tub were closed. they provide fresh linens and towels as needed. They are very prompt and answer the phone quickly. The parking is secure and well lit. Location is in a safe neighborhood. Across the street is disco pancakes for breakfast. Target is just down the road and CVS and Jewel grocery stores. This is our second time staying. When we do stay, we stay about a week. It is quiet. Great views.
Reviewed on Dec 3, 2025

The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $581, price is now $340 per person
$340
per person
Feb 13 - Feb 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Yes room was clean and orderly with everything in place. Front desk and dining staff were professional and thoughtful. Music in restaurant was a bit high for volume, more relaxing type of music would be nice. Food was good and happy hour specials were nice. enjoyed our stay.
Reviewed on Nov 26, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $656, price is now $391 per person
$391
per person
Feb 13 - Feb 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
It's always perfection at the Trump. King suite with Lake view is the ultimate
Reviewed on Dec 2, 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $429, price is now $257 per person
$257
per person
Feb 4 - Feb 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,229 reviews)
Wonderful ! Clean ! Staff helpful! Great location near everything beautiful views !
Reviewed on Dec 5, 2025
Find the Best Waukesha County Vacation Packages
Waukesha County Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | General Mitchell Intl. Airport (MKE) |
Top Sights | Kettle Moraine Ranch, Fowler Lake Park and Little Muskego Lake |
Waukesha County Hotel Deals

Country Inn & Suites by Radisson, Milwaukee West (Brookfield), WI
1250 S Moorland Rd Brookfield WI
Fully refundable
$93 nightly
The price is $107 total per night from Dec 14 to Dec 15
$107 total
Dec 14 - Dec 15
Total with taxes and fees
8.6/10 Excellent! (1,244 reviews)
Quickest check-in, warm and inviting entrance, very clean, comfortable bed and pillows, hot breakfast. All staff were kind and helpful. Fresh cookies at check-in were the cherry on top of my wonderful stay!
Reviewed on Nov 30, 2025

Embassy Suites by Hilton Milwaukee Brookfield
1200 S Moorland Rd Brookfield WI
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $115 total per night from Dec 18 to Dec 19
$115 total
Dec 18 - Dec 19
Total with taxes and fees
8.8/10 Excellent! (1,012 reviews)
Clean
Reviewed on Dec 3, 2025

Sonesta Select Milwaukee Brookfield
16865 W Bluemound Rd Brookfield WI
Fully refundableReserve now, pay when you stay
$74 nightly
The price is $85 total per night from Dec 11 to Dec 12
$85 total
Dec 11 - Dec 12
Total with taxes and fees
8/10 Very Good! (1,362 reviews)
Good
Reviewed on Nov 26, 2025
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.
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