Southwest Wisconsin 2024 Holidays

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Top Flight + Hotel Deals in Southwest Wisconsin

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
per person
28 Jun - 3 Jul
found 15 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8/10 Very Good! (1,023 reviews)
The hotel was super clean! The staff was amazing. Definitely will stay there again

Reviewed on 24 May 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
28 Jun - 3 Jul
found 15 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,190 reviews)
Great view and environment

Reviewed on 23 May 2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
28 Jun - 3 Jul
found 15 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.8/10 Excellent! (207 reviews)
Thoroughly enjoyed my stay and my room. Will definitely book here again. Basic view of the courtyard but that was not important to me.

Reviewed on 16 Mar 2024

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
28 Jun - 3 Jul
found 15 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (687 reviews)
Beautiful property, lovely staff, very well-located for a weekend trip to Chicago where we needed to be near the Loop.

Reviewed on 23 May 2024

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
per person
28 Jun - 3 Jul
found 15 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.6/10 Excellent! (1,138 reviews)
My room was clean and staff friendly.

Reviewed on 21 May 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

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 €26 per night from 2 Jun to 3 Jun
€26
per night
2 Jun - 3 Jun
6.2/10 (1,842 reviews)
"Great"

Reviewed on 22 May 2024

Mt. Olympus Water & Theme Park Resort
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 €148 per night from 26 May to 27 May
€148
per night
26 May - 27 May
9.2/10 Wonderful! (1,615 reviews)
"This was a very short stay with an early checkout (4 a.m.) but it would have been great to start longer and appreciate it more. A beautiful place with friendly staff and comfortable rooms. I would definitely come back again."

Reviewed on 23 May 2024

The Madison Concourse Hotel and Governor's Club
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 €160 per night from 26 May to 27 May
€160
per night
26 May - 27 May
9/10 Wonderful! (1,000 reviews)
"Friendly staff and very clean room. Seems recently remodeled."

Reviewed on 17 May 2024

Best Western Plus InnTowner Madison
See all 3,772 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 €995, 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

Image for University of Wisconsin-Madison

University of Wisconsin-Madison

5/5(2 reviews)

Enjoy the student vibe around University of Wisconsin-Madison, a top university in Madison. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

University of Wisconsin-Madison
Image for Mt. Olympus Water and Theme Park

Mt. Olympus Water and Theme Park

Have a fun-filled day at Mt. Olympus Water and Theme Park and see why people love this theme park in Wisconsin Dells. Stroll along the area's riverfront or experience its entertainment choices.

Mt. Olympus Water and Theme Park
Image for Devil's Lake State Park

Devil's Lake State Park

Explore the great outdoors at Devil's Lake State Park, a lovely green space in Wisconsin Dells. Stroll along the lakeside or visit the fun-filled water parks in this family-friendly area.

Devil's Lake State Park

More trip options

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