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.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was €1,991, price is now €1,225 per person
€1,225
per person
2 Nov - 7 Nov
found 16 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
The hotel was above the expectations and river view was fabulous also staff were incredibly awesome specially the front dest employee Natalia she was helpful, smiling and welcoming.
Reviewed on 24 Sept 2025
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was €2,128, price is now €1,350 per person
€1,350
per person
2 Nov - 7 Nov
found 16 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
Got pick pocketed in the elevator. I really like this hotel. Plan to return.
Reviewed on 8 Sept 2025
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was €1,216, price is now €780 per person
€780
per person
2 Nov - 7 Nov
found 18 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
The room was perfect and the front staff were exceptional. Our stay was amazing!
Reviewed on 21 Sept 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
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! (3,103 reviews)
AMAZING HOTEL!
"This hotel is AMAZING!!!! The staff is wonderful, service superb, restaurant fabulous! An absolute joy to stay here!"
Reviewed on 18 Sept 2025
Baymont by Wyndham Madison West/Middleton WI West
8102 Excelsior Dr, Madison, WI
Fully refundableReserve now, pay when you stay
The price is €71 per night from 5 Oct to 6 Oct
€71
5 Oct - 6 Oct
includes taxes & fees
8/10 Very Good! (1,022 reviews)
"great, "cheaper" option in the area... Breakfast is pretty unhealthy, but it's free so..."
Reviewed on 22 Sept 2025
Mt. Olympus Water & Theme Park Resort
655 N. Frontage Road, Wisconsin Dells, WI
Fully refundableReserve now, pay when you stay
The price is €95 per night from 26 Sept to 27 Sept
€95
26 Sept - 27 Sept
includes taxes & fees
6.8/10 (2,437 reviews)
"Very nice Happy with Mt. Olimpus"
Reviewed on 22 Sept 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 Wisconsin Dells. Stroll along the area's riverfront or experience its entertainment choices.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
