Southwest Wisconsin Vacation Packages
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Top Southwest Wisconsin vacation package deals
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
9.4/10 Exceptional! (5,555 reviews)
Jan 14 - Jan 18
4 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Price was $676, price is now $447 per person
$447
per person
found 1 day ago
I was welcomed by the staff, the place was clean and well ventilated. The bed was comfortable, and the breakfast buffet was on point. Highly recommend this hotel.
Reviewed on Nov 14, 2026
4.5-star property
Pendry Chicago
Downtown Chicago
9.2/10 Wonderful! (1,161 reviews)
Jan 15 - Jan 18
3 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Price was $633, price is now $437 per person
$437
per person
found 1 day ago
The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back.
Reviewed on Nov 8, 2026
Top rated hotels for your Southwest Wisconsin vacation package
The Madison Concourse Hotel and Governor's Club
1 W Dayton St Madison WI
Free Cancellation
Reserve now, pay when you stay
41.95 mi from city center
$127 nightly
The price is $146 total per night
$146 total
Nov 16 - Nov 17
Total with taxes and fees
Guests of The Madison Concourse Hotel and Governor's Club have access to an indoor pool, a gym, and a sauna. If you drive, self parking is USD 20 per night, or you can take advantage of the free airport shuttle (available on request). Front-desk staff can answer questions 24/7, and assist with luggage storage, concierge services, and dry cleaning/laundry. Other amenities at this luxury hotel include free WiFi in public areas, a hot tub, and a conference center.
Motel 6 Madison, WI - East
4202 E Towne Blvd Madison WI
Free Cancellation
43.09 mi from city center
$53 nightly
The price is $61 total per night
$61 total
Dec 4 - Dec 5
Total with taxes and fees
Motel 6 Madison, WI - East features free WiFi in public areas, express check-in, and express check-out. Free parking is available if you drive. The 24-hour front desk has staff always at the ready. Additional amenities include laundry facilities and a vending machine.
Natura Vue Resort & Boathouse
1015 River Rd Wisconsin Dells WI
18.07 mi from city center
$85 nightly
The price is $95 total per night
$95 total
Nov 15 - Nov 16
Total with taxes and fees
Guests of Natura Vue Resort & Boathouse enjoy a marina, an indoor pool, and a children's pool. Limited parking is available. The front desk has multilingual staff standing by 24 hours a day to assist with securing valuables and tours/tickets. Other amenities at this beach hotel include a sauna, free WiFi in public areas, and a hot tub.
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View all propertiesLowest 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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