
Waukesha County Holidays
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Top destinations in Waukesha County

Milwaukee
Top Flight + Hotel Deals in Waukesha County
Price found within the past 48 hours. Click for updated prices.

The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Save 100% on your flight
per person
24 Sept - 2 Oct
found 21 hours ago
Return direct flight included
Shannon (SNN) to Chicago (ORD)
8.8/10 Excellent! (1,925 reviews)
Overall the staff were very prompt and helpful. My only complaints with the hotel is the rooms are smaller than I expected, the 4 of us had a hard time fitting into a double bed room. It would have been nice to know that most of the food places around the hotel close on the weekend. Definitely not the best choice for a family. Proximity to activities were doable , but a little far. Wells street at night was a little scary over the weekend. Parking in Chicago is really crazy but I found parking for $18 a night on the same block without in and out access. We parked and left the car the whole time. Overall staff was amazing, nothing bad to say there, but I was disappointed as a first time visitor with the size of the hotel rooms, the cleanliness was fair, dark room, windows you couldn’t see out of well. The room temp was set at 65 but we were all swearing overnight and had to purchase a fan to help.
Reviewed on 13 Aug 2025


Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
per person
24 Sept - 2 Oct
found 21 hours ago
Return direct flight included
Shannon (SNN) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
Terrace 16 resto has the best view in Chicago outstanding service.
Hotel is located right next to the river cruises.
Walgreens is 3 minutes away by foot.
Very safe neighborhood several excellent restaurants within 10 minutes on foot.
Try Wildberry resta for breakfast excellent food.
Sanda for Asian food and Grand Boucher French
The pizza place next to hotel (bonjiourno) overrated and subpar
Reviewed on 12 Aug 2025


Level Chicago - River North
Downtown Chicago
Save 100% on your flight
per person
24 Sept - 2 Oct
found 21 hours ago
Return direct flight included
Shannon (SNN) to Chicago (ORD)
9/10 Wonderful! (654 reviews)
Quick and easy check in. Parking in their private garage was breeze. Plenty of space, mostly empty, and our vehicle could stay in the garage until 2:00 PM the next day. Beautiful 1 BR condo. Full kitchen, beautiful views of the city on the balcony and from the living room, and very clean space overall. Need your key card for just about everything (pool, lounge, some of the outdoor bathrooms, elevators, etc.).
Reviewed on 27 Jul 2025
Top hotels in Waukesha County

Sheraton Milwaukee Brookfield Hotel
375 S Moorland Rd, Brookfield, WI
The price is €86 per night from 31 Aug to 1 Sept
€86
31 Aug - 1 Sept
includes taxes & fees
8.2/10 Very Good! (387 reviews)
"Comfortable beds and clean hotel"
Reviewed on 13 Aug 2025

Sonesta Select Milwaukee Brookfield
16865 W Bluemound Rd, Brookfield, WI
The price is €86 per night from 19 Aug to 20 Aug
€86
19 Aug - 20 Aug
includes taxes & fees
8/10 Very Good! (1,241 reviews)
"The hotel was great. The only issue was checkin. System was down and it didn’t come back up. One staff member said he couldn’t do anything until system was back up - which it still was not up 8 hours later. One staff member did allow us to check in manually thankfo."
Reviewed on 11 Aug 2025

Country Inn & Suites by Radisson, Milwaukee West (Brookfield), WI
1250 S Moorland Rd, Brookfield, WI
The price is €100 per night from 1 Sept to 2 Sept
€100
1 Sept - 2 Sept
includes taxes & fees
8.8/10 Excellent! (1,072 reviews)
Awesome
"This hotel was awesome! Great service, fun pool and hot tub. Comfortable beds and cozy room. Great restaurant right next door. Will definitely stay again!"
Reviewed on 11 Aug 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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