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)
Dec 17 - Dec 20
3 night stay
Denver (DEN) to Chicago (ORD)
Southwest Airlines • Coach
Chicago (ORD) to Denver (DEN)
Frontier Airlines • Coach
Price was $765, price is now $552 per person
$552
per person
found 1 day ago
4.0-star property
Level Chicago Fulton Market
Downtown Chicago
9.2/10 Wonderful! (591 reviews)
Dec 14 - Dec 18
4 night stay
Houston (IAH) to Chicago (ORD)
American Airlines • Coach
Chicago (ORD) to Houston (IAH)
Frontier Airlines • Coach
Price was $809, price is now $577 per person
$577
per person
found 1 day ago
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
9.6/10 Exceptional! (2,057 reviews)
Dec 14 - Dec 18
4 night stay
Houston (IAH) to Chicago (ORD)
American Airlines • Coach
Chicago (ORD) to Houston (IAH)
Frontier Airlines • Coach
Price was $1,409, price is now $1,051 per person
$1,051
per person
found 1 day ago
Had a good stay. Will come again
Reviewed on Nov 2, 2026
2.0-star property
The Dunes Hotel
8/10 Very Good! (672 reviews)
Dec 23 - Dec 28
5 night stay
Denver (DEN) to Chicago (ORD)
American Airlines • Coach
Chicago (ORD) to Denver (DEN)
Frontier Airlines • Coach
Price was $754, price is now $562 per person
$562
per person
found 9 hours ago
The hotel is in an amazing location. The beach is beautiful and clean and quiet. I was here during the off season and it felt like we had the place to ourselves. The room was exactly as expected, clean, stocked, and quiet. The staff was kind and so easy checking in and out. I was able to check in hours earlier and there was no issues or extra fees. There is no gym or pool available. They do charge for Coffee and snacks in the lobby but there's always some snacks there if you're hungry. They have restaurant hours but we didn't explore that. Instead we tried some local spots. Great place to get away and get some peace.
Reviewed on Oct 31, 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 24 - Nov 25
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 concierge services, dry cleaning/laundry, and luggage storage. Other amenities at this luxury hotel include free WiFi in public areas, a hot tub, and a conference center.
Pool
Hot Tub
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 3 - Nov 4
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 concierge services. Other amenities at this beach hotel include a sauna, free WiFi in public areas, and a hot tub.
Pool
Hot Tub
Motel 6 Madison, WI - East
4202 E Towne Blvd Madison WI
Free Cancellation
43.09 mi from city center
$44 nightly
The price is $51 total per night
$51 total
Nov 16 - Nov 17
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.
Pet friendly
Parking included
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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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