Southwest Wisconsin Holidays

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    Save up to €185 when you book a flight and hotel together*
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Top Flight + Hotel Deals in Southwest Wisconsin

Price found within the past 48 hours. Click for updated prices.
21c Museum Hotel Chicago

21c Museum Hotel Chicago

4 out of 5
Downtown Chicago
per person
14 Mar - 18 Mar
found 1 day ago
Return direct flight included
Vancouver (YVR) to Chicago (ORD)
8.6/10 Excellent! (1,887 reviews)
Nice recent renovated hotel, building is old but has good shower water pressure. However, the ac is tooooo loud.

Reviewed on 3 Jan 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
14 Mar - 18 Mar
found 1 day ago
Return direct flight included
Vancouver (YVR) to Chicago (ORD)
9/10 Wonderful! (279 reviews)
Great property and staff

Reviewed on 29 Dec 2024

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
14 Mar - 18 Mar
found 1 day ago
Return direct flight included
Vancouver (YVR) to Chicago (ORD)
9.2/10 Wonderful! (1,253 reviews)
Always friendly and clean hotel. Love the club access on the too floor.

Reviewed on 5 Jan 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
14 Mar - 18 Mar
found 1 day ago
Return direct flight included
Vancouver (YVR) to Chicago (ORD)
9.4/10 Exceptional! (3,575 reviews)
Beautiful hotel right on the river. Perfectly located to walk to shops, restaurants, and top sites of downtown Chicago. The rooms were clean, comfortable, and quiet. I would recommend you eat outside the hotel. The food was expensive and just average. I would stay here again if ever back in Chicago.

Reviewed on 5 Jan 2025

Hilton Orrington / Evanston

Hilton Orrington / Evanston

4 out of 5
per person
14 Mar - 21 Mar
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
7.6/10 Good! (1,002 reviews)
I was lucky enough to be in one of the newly renovated rooms and it was lovely. The staff, especially Sophia, were excellent and very friendly.

Reviewed on 1 Jan 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
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 €156 per night from 12 Jan to 13 Jan
€156
includes taxes & fees
12 Jan - 13 Jan
9.4/10 Exceptional! (2,219 reviews)
"Clean, friendly staff. Governors club is amazing and worth it."

Reviewed on 4 Jan 2025

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 €72 per night from 6 Jan to 7 Jan
€72
includes taxes & fees
6 Jan - 7 Jan
6.6/10 (1,927 reviews)
"If you go in the winter only book a room at Hotel Rome. That’s connected to the indoor water park and theme park… You will have to walk outside for a quick second to get the the Theme Park… The water park we didn’t have to go outside at all to get to it… It was very close."

Reviewed on 25 Dec 2024

Mt. Olympus Water & Theme Park Resort
Atlantis Family Waterpark Hotel, Ascend Hotel Collection
Atlantis Family Waterpark Hotel, Ascend Hotel Collection
3 out of 5
1570 Wisconsin Dells Pkwy, Wisconsin Dells, WI
Fully refundableReserve now, pay when you stay
The price is €75 per night from 27 Jan to 28 Jan
€75
includes taxes & fees
27 Jan - 28 Jan
7.2/10 Good! (649 reviews)
"Very nice room"

Reviewed on 1 Jan 2025

Atlantis Family Waterpark Hotel, Ascend Hotel Collection
See all 3,596 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 €803, 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.