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.
Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
per person
26 Dec - 30 Dec
found 13 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.4/10 Very Good! (1,387 reviews)
Beautiful hotel, quiet clean spacious rooms! Breakfast buffett to die for. Close to museums and Metro.

Reviewed on 24 Nov 2024

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
26 Dec - 30 Dec
found 13 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (888 reviews)
We had multiple issues with the locks on our door.

Reviewed on 24 Nov 2024

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
26 Dec - 30 Dec
found 13 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,378 reviews)
Andy at the front desk was amazing and so professional! Just based on the service he provided, I will be back! Hotel is in an excellent location as well! Would definitely recommend!

Reviewed on 25 Nov 2024

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
26 Dec - 30 Dec
found 13 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (809 reviews)
Lobby and shared space downstairs is beautiful and location is great in Fulton Market. We walked to many bars and restaurants and enjoyed the vibe. The rooms are underwhelming, no closet space, bathroom space lacking, and feel dated despite trying to go for a modern-industrial-chic vibe. The quality of the rooms do not match what the lobby area indicates. The hallways seem like they didn’t get touched in whatever remodel happened here. Overall I think it’s overpriced for what it delivers.

Reviewed on 20 Nov 2024

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
per person
26 Dec - 30 Dec
found 13 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.6/10 Excellent! (2,625 reviews)
The location was amazing!

Reviewed on 24 Nov 2024

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
Madison featuring flowers, a house and a garden

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.

Find hotels in Downtown Madison

Top hotels in Southwest Wisconsin

The Madison Concourse Hotel and Governor's Club
The Madison Concourse Hotel and Governor's Club
3.5 out of 5
1 W Dayton St, Madison, WI
Fully refundableReserve now, pay when you stay
The price is €123 per night from 1 Dec to 2 Dec
€123
includes taxes & fees
1 Dec - 2 Dec
9.4/10 Exceptional! (2,096 reviews)
"This was a great place to stay for the Oregon/Wisconsin game. The staff were super friendly. The airport shuttle was very convenient. And the location of this hotel was perfect! Within walking distance to so much. Highly recommend!"

Reviewed on 23 Nov 2024

The Madison Concourse Hotel and Governor's Club
Mt. Olympus Water & Theme Park Resort
Mt. Olympus Water & Theme Park Resort
3 out of 5
655 N. Frontage Road, Wisconsin Dells, WI
Fully refundableReserve now, pay when you stay
The price is €71 per night from 2 Dec to 3 Dec
€71
includes taxes & fees
2 Dec - 3 Dec
6.6/10 (1,912 reviews)
"Very economical. Some trade offs but worth it."

Reviewed on 18 Nov 2024

Mt. Olympus Water & Theme Park Resort
Best Western Plus InnTowner Madison
Best Western Plus InnTowner Madison
3 out of 5
2424 University Avenue, Madison, WI
Fully refundableReserve now, pay when you stay
The price is €120 per night from 8 Dec to 9 Dec
€120
includes taxes & fees
8 Dec - 9 Dec
9/10 Wonderful! (1,003 reviews)
"Great buffet breakfast and free happy hour hotdogs and beers before the Wisconsin Oregon game. Remodeled guest rooms with new tile shower. Very friendly and helpful staff."

Reviewed on 18 Nov 2024

Best Western Plus InnTowner Madison
See all 3,558 properties in Southwest Wisconsin
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.

Frequently asked questions

How much does a Southwest Wisconsin holiday package cost?
Starting from an incredible €653, you can handcraft your own Southwest Wisconsin package. Simply bundle flights, hotels and car rentals and be rewarded with discounts.
How do I get a cheap travel package to Southwest Wisconsin?
If you love scoring a bargain, bundle your bookings into a Southwest Wisconsin holiday package. Whether you’re looking for hotels, flights, activities or rental cars, you can browse and book them all in one place. You’ll have lots of choice at your fingertips too. Expedia has over 550 air carriers and 1,000,000 hotel options globally to pick from. Fly with who you prefer, book a room where you like and save a tidy sum — now that’s the ideal escape!
What are the top hotels in Southwest Wisconsin?
Chula Vista Resort, Trademark Collection by Wyndham and Adams Inn know how to make their guests feel at home in Wisconsin Dells. If your travel plans also include Baraboo, check out La Quinta Inn & Ste by Wyndham Wisconsin Dells- Lake Delton and Days Inn & Suites by Wyndham Wisconsin Dells. Both are popular with travellers.
How far in advance should I book my Southwest Wisconsin holiday?
It all depends on the airline, but you can usually look up international fares on Expedia up to 12 months in advance. While it’s generally a good idea to book ahead of time, lucky travellers occasionally score a cheaper flight just weeks prior to the date of departure.
What does an Expedia Southwest Wisconsin travel package include?
Travel packages include hotels, rental cars and flights, but you can combine any of them to create your ideal Southwest Wisconsin getaway. You can also add on a few tours and activities once you’ve made your booking. You’re in control! When you combine your bookings with Expedia, you’ll score deals you won’t find elsewhere.
What should I know before booking a Southwest Wisconsin travel package?
You’ll pick up impressive savings when you combine your hotels, flights and rental cars into a package. Plus, booking everything together will make your trip planning easier. So why waste your time or money? Whether you’re organising a luxury city stay with your love or an affordable family break, check out our holiday packages today.
Can I choose my airline with a Southwest Wisconsin Expedia holiday package?
You can. We have more than 550 partner airlines globally, so go with the carrier that matches your budget and travelling style.
If I'm not able to travel, can I cancel my Southwest Wisconsin holiday package?
Yes, it’s possible to cancel your Southwest Wisconsin booking if your travel plans have changed. Whether you’ll be charged a fee or not depends on your airline, hotel or car rental company. It may be possible to cancel or change your booking for free if you booked in the last 24 hours. Visit our Customer Service Portal for more information.

Popular places to visit

Noah's Ark Waterpark

Bring the family to Noah's Ark Waterpark and have a fun-filled day at this theme park in Lake Delton. Stroll along the area's riverfront or experience its entertainment choices.

Noah's Ark Waterpark
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.