
Southwest Wisconsin Holidays
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Top Flight + Hotel Deals in Southwest Wisconsin
Price found within the past 48 hours. Click for updated prices.

The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
per person
30 Oct - 3 Nov
found 5 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.8/10 Excellent! (1,925 reviews)
The location was good. Staff was friendly. It was clean. But it was hard to enjoy time in the room because of the TV. They had horrible cable with nothing on, and it wasn’t a smart tv so we couldn’t log into any of our streaming services or even stream from our phones to the tv. We had to go out and buy a firestick.
Reviewed on 10 Aug 2025

Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
per person
30 Oct - 3 Nov
found 5 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,270 reviews)
Great hotel and great service! Would definitely recommend to anyone staying in the Mag mile area. The breakfast buffet was really good and convenient. The room was very comfortable and spacious.
Reviewed on 11 Aug 2025

Pendry Chicago
Downtown Chicago
per person
30 Oct - 3 Nov
found 5 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,033 reviews)
Gorgeous hotel. Hotel staff in all areas were extremely professional and helpful to include front desk, concierge, bar tenders, hostess and cleaning crew.
Reviewed on 10 Aug 2025


Bluegreen Vacations Hotel Blake, Ascend Resort Collection
Downtown Chicago
per person
30 Oct - 3 Nov
found 5 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,005 reviews)
Comfortable bed and walkable but rooms can be noisy for outside noises
Reviewed on 10 Aug 2025
Where to stay in Southwest Wisconsin
Find the best Southwest Wisconsin areas and neighborhoods for the activities you enjoy most. Learn more about Southwest Wisconsin

Downtown Madison
The ample dining options and fantastic lake views are top of the list for many visitors to Downtown Madison. A stop by Orpheum Theater or Overture Center for the Arts might round out your trip.
Top hotels in Southwest Wisconsin

Mt. Olympus Water & Theme Park Resort
655 N. Frontage Road, Wisconsin Dells, WI
Fully refundableReserve now, pay when you stay
The price is €39 per night from 1 Sept to 2 Sept
€39
1 Sept - 2 Sept
includes taxes & fees
6.8/10 (2,296 reviews)
"We stayed in the 2 queen bed with bunkbeds room Very spacious and clean went during the week so crowds were less. Awesome value with the free access to everything and free parking at the parks. We had a blast . Had an issue with our tv and they sent someone out right away!"
Reviewed on 8 Aug 2025

Days Inn & Suites by Wyndham Wisconsin Dells
2504 Wisconsin Dells Parkway, Wisconsin Dells, WI
Fully refundableReserve now, pay when you stay
The price is €46 per night from 1 Sept to 2 Sept
€46
1 Sept - 2 Sept
includes taxes & fees
7/10 Good! (1,505 reviews)
"Not much bad to say about this location other than the bed was quite old. Room was nice, was not woken up by other room noise, good water pressure and wifi, the pool was a great value add and the room had a micro/fridge/coffee pantry which is always great. Note also great location, can walk into ..."
Reviewed on 7 Aug 2025

The Madison Concourse Hotel and Governor's Club
1 W Dayton St, Madison, WI
Fully refundableReserve now, pay when you stay
9.4/10 Exceptional! (2,957 reviews)
"The most comfortable beds EVER. I even took a picture of the tags so I can get the same exact one! Love this hotel! My rant has stayed there at least 10 times and will keep coming back!"
Reviewed on 9 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.
Popular places to visit
Noah's Ark Waterpark
Have a fun-filled day at Noah's Ark Waterpark and find out why this is a popular theme park in Lake Delton. Stroll along the area's riverfront or experience its entertainment choices.
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