Southern Wisconsin Holidays
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Top Flight + Hotel Deals in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North
Downtown Chicago
Save 100% on your flight
Price was €998, price is now €576 per person
€576
per person
31 Oct - 6 Nov
found 15 hours ago
Return flight included
Nashville (BNA) to Chicago (ORD)
9.2/10 Wonderful! (2,052 reviews)
Excellent staff very friendly
Reviewed on 29 Aug 2025
The Emily Hotel
Downtown Chicago
Price was €1,487, price is now €781 per person
€781
per person
31 Oct - 6 Nov
found 15 hours ago
Return flight included
Nashville (BNA) to Chicago (ORD)
9.2/10 Wonderful! (1,192 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend.
Also the coffee bags ? PERFECTION. Just had to add that
Reviewed on 22 Aug 2025
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was €1,099, price is now €603 per person
€603
per person
31 Oct - 6 Nov
found 15 hours ago
Return flight included
Nashville (BNA) to Chicago (ORD)
9/10 Wonderful! (343 reviews)
It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.
Reviewed on 27 Aug 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was €2,381, price is now €1,344 per person
€1,344
per person
31 Oct - 6 Nov
found 14 hours ago
Return direct flight included
Nashville (BNA) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
5 star hotel that goes above and beyond. My family loved staying at the Trump
Reviewed on 29 Aug 2025
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was €2,650, price is now €1,559 per person
€1,559
per person
31 Oct - 6 Nov
found 13 hours ago
Return direct flight included
Nashville (BNA) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!
Reviewed on 10 Aug 2025
Where to stay in Southern Wisconsin
Find the best Southern Wisconsin areas and neighborhoods for the activities you enjoy most. Learn more about Southern Wisconsin
Downtown Milwaukee
Lake Michigan and Pabst Theater are a few top attractions in Downtown Milwaukee. Hop around the city on the metro at Michigan & Jackson Tram Stop or Clybourn & Jefferson Tram Stop and check out the area's fantastic nightlife, stunning river views and acclaimed art galleries.
Top hotels in Southern Wisconsin
Mt. Olympus Water & Theme Park Resort
655 N. Frontage Road, Wisconsin Dells, WI
Fully refundableReserve now, pay when you stay
The price is €43 per night from 8 Sept to 9 Sept
€43
8 Sept - 9 Sept
includes taxes & fees
The Madison Concourse Hotel and Governor's Club
1 W Dayton St, Madison, WI
Fully refundableReserve now, pay when you stay
Sonesta Select Milwaukee Brookfield
16865 W Bluemound Rd, Brookfield, WI
Fully refundableReserve now, pay when you stay
The price is €75 per night from 18 Sept to 19 Sept
€75
18 Sept - 19 Sept
includes taxes & fees
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
Harley-Davidson Museum
4.5/5(3 reviews)
Delve into the history of one of the world’s most famous motorcycle brands via interactive exhibits, photo galleries, workshops and behind-the-scenes tours.
Milwaukee County Zoo
This sprawling animal park houses a wide array of exotic wildlife, and is acclaimed for its conservation programs and educational resources.
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.