
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
per person
15 Sept - 19 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,659 reviews)
Very friendly staff, hotel needs renovation. Pool dated some stones missing by pool & ceiling needs painting.
Reviewed on 4 Aug 2025

LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
per person
15 Sept - 19 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,342 reviews)
London house did not disappoint. View room was a highlight, staff were friendly and courteous. Close walk to Riverwalk, tours, parks, museums and shops. Make reservations for LH rooftop. I only wish I was able to get credit with Hilton for the stay.
Reviewed on 3 Aug 2025


Level Chicago - River North
Downtown Chicago
per person
15 Sept - 19 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (652 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
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 €87 per night from 17 Aug to 18 Aug
€87
17 Aug - 18 Aug
includes taxes & fees
6.8/10 (2,278 reviews)
"Room was clean and specious."
Reviewed on 3 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! (1,492 reviews)
"Great time. Wonderful property."
Reviewed on 2 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! (2,934 reviews)
"Great location, really nice rooms, comfy beds, walkable fun times."
Reviewed on 4 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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