Southwest Wisconsin Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Choose two or more items and save on your trip:
    Plan, book, travel with confidence
  • payments icon
    Better together
    Save up to CA $775 when you book a flight and hotel together*
  • lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Top Southwest Wisconsin Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 28 - Aug. 3
Roundtrip non-stop flight included
Ottawa (YOW) 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 Mar. 16, 2024

Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 28 - Aug. 3
Roundtrip non-stop flight included
Ottawa (YOW) to Chicago (ORD)
9.2/10 Wonderful! (96 reviews)
Outstanding service and facility.

Reviewed on Jan. 10, 2024

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 28 - Aug. 3
Roundtrip non-stop flight included
Ottawa (YOW) to Chicago (ORD)
8.6/10 Excellent! (189 reviews)
This hotel has a managing problem.

Reviewed on May 13, 2024

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 28 - Aug. 3
Roundtrip non-stop flight included
Ottawa (YOW) to Chicago (ORD)
9.6/10 Exceptional! (976 reviews)
Everything exceeded our expectations and would highly recommend! Stunning rooms that make the Ritz and Four Seasons look pathetic!

Reviewed on May 2, 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 28 - Aug. 3
Roundtrip non-stop flight included
Ottawa (YOW) to Chicago (ORD)
9.2/10 Wonderful! (1,190 reviews)
The best hotel hands down!

Reviewed on May 13, 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 showing a garden, a house and flowers

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 hotel + flight trips in Downtown Madison

Southwest Wisconsin Hotel Deals

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 CA $175 per night from May 22 to May 23
CA $175
CA $203 total
includes taxes & fees
May 22 - May 23
9.2/10 Wonderful! (1,598 reviews)
"Lovely property great stay!"

Reviewed on May 13, 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 CA $34 per night from May 19 to May 20
CA $34
CA $84 total
includes taxes & fees
May 19 - May 20
6.2/10 (1,827 reviews)
"Excellent service I’m really recommend"

Reviewed on May 14, 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 CA $204 per night from May 27 to May 28
CA $204
CA $236 total
includes taxes & fees
May 27 - May 28
9/10 Wonderful! (1,000 reviews)
"Good location, clean & safe."

Reviewed on May 10, 2024

Best Western Plus InnTowner Madison
See all 3,781 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Southwest Wisconsin vacation package cost?
Starting from an incredible CA $1,890, 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 vacation 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 travelers.
How far in advance should I book my Southwest Wisconsin vacation?
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 travelers 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 organizing a luxury city stay with your love or an affordable family break, check out our vacation packages today.
Can I choose my airline with a Southwest Wisconsin Expedia vacation package?
You can. We have more than 550 partner airlines globally, so go with the carrier that matches your budget and traveling style.
If I'm not able to travel, can I cancel my Southwest Wisconsin vacation 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.

Discover the most popular places to visit in Southwest Wisconsin

Image for University of Wisconsin-Madison

University of Wisconsin-Madison

4.5/5(7 reviews)

Enjoy the collegiate vibe around University of Wisconsin-Madison, a top college 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

5/5(3 reviews)

Enjoy the rides and games at Mt. Olympus Water and Theme Park and see why this is a favorite amusement 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 waterparks in this family-friendly area.

Devil's Lake State Park

Other vacations you might like

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