Southern Wisconsin Vacation Packages

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Your Southern Wisconsin Vacation

Our Southern Wisconsin vacation packages provide an easy, affordable and immersive way to experience everything this incredible destination has to offer. If it's distilleries and craft breweries and dining you're after, this is the place to be. With so much to see and do on a trip to Southern Wisconsin, it can be hard to know where to begin. Kick off your journey in Milwaukee at American Family Field and Wisconsin State Fair Park — two much-loved attractions here. Another city worthy of a spot on your itinerary is Wisconsin Dells. Be sure not to miss Mt. Olympus Water and Theme Park and Chula Vista Waterparks. Expedia is a one-stop shop when it comes to organizing your Southern Wisconsin vacation. From hotels and flights, to car rentals and more, we know how to curate a travel experience like no other.

Top Southern Wisconsin Vacation Deals

Price found within the past 48 hours. Click for updated prices.
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Price was CA $964, price is now CA $687 per person
CA $687
per person
Aug 21 - Aug 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,003 reviews)
I was double billed after being assured I would not be charged by both agent and hotel when I saw the hold, as it was a prepaid booking via Expedia

Reviewed on Jul 13, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $1,141, price is now CA $728 per person
CA $728
per person
Aug 21 - Aug 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,020 reviews)
Clean rooms, nice pool, location great

Reviewed on Jul 12, 2026

Renaissance Chicago Downtown Hotel

Renaissance Chicago Downtown Hotel

4 out of 5
Downtown Chicago
Price was CA $1,073, price is now CA $732 per person
CA $732
per person
Aug 21 - Aug 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,002 reviews)
Great stay perfect location

Reviewed on Jul 12, 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was CA $1,097, price is now CA $749 per person
CA $749
per person
Aug 21 - Aug 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
While amenities and being up to date are important, my main focus for a hotel is it’s cleanliness and how comfortable is the bed since I’ve stayed many places that while nice, if the bed is uncomfortable can ruin your stay. Our room at Omni was clean and comfortable. There were a few things that looked a little tired and could use updating but overall we had a good sleep and were refreshed for the next day.

Reviewed on Jul 13, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $2,089, price is now CA $1,466 per person
CA $1,466
per person
Sep 18 - Sep 22
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
Very clean nice workers and amazing views

Reviewed on Jul 14, 2026

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
A river with a city skyline, including a tall building with a pointed roof, and a park with yellow trees.

Downtown Milwaukee

Central business district with cultural, financial, and historical landmarks, Downtown Milwaukee offers shopping at The Shops of Grand Avenue, art galleries in the Historic Third Ward, high-end dining, and vibrant nightlife. Explore the Milwaukee Public Market and Riverwalk, or hop on the free streetcar system.

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Southern Wisconsin Hotel Deals

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 $156 per night from Aug 4 to Aug 5
CA $156
CA $175 total
Aug 4 - Aug 5
includes taxes & fees
7/10 Good! (2,869 reviews)
"Clean room, easy check in, no complaints"

Reviewed on Jul 13, 2026

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 CA $205 per night from Aug 2 to Aug 3
CA $205
CA $236 total
Aug 2 - Aug 3
includes taxes & fees
9.4/10 Exceptional! (4,005 reviews)
"Lots of great things at this place. The only reason we docked a point is because we felt the staff in the bar were bit condescending after they realized that i was not drinking. Obviously, their choice to run their joint as they wish, but it didn’t sit well with us."

Reviewed on Jul 14, 2026

The Madison Concourse Hotel and Governor's Club
Harbor Shores on Lake Geneva

Harbor Shores on Lake Geneva

3.5 out of 5
300 Wrigley Dr Lake Geneva WI
Fully refundableReserve now, pay when you stay
The price is CA $253 per night from Jul 20 to Jul 21
CA $253
CA $319 total
Jul 20 - Jul 21
includes taxes & fees
9.2/10 Wonderful! (1,378 reviews)
"We stayed at Harbor Shores for two nights and it was great! It’s literally across the street from the lake and a minutes walk from anywhere in downtown. The staff provided a list of suggestions on where to go for the best dining and each place we tried was excellent. The room was nice and had everything ..."

Reviewed on Jul 13, 2026

Harbor Shores on Lake Geneva
See all 7,703 properties in Southern 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.
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Stay near popular Southern Wisconsin attractions

A baseball game in a stadium with a person holding a hot dog and a drink.
Photo by Tim Ard
Open Photo by Tim Ard

American Family Field

9.0/10 (2,832 reviews)
Catch an event at American Family Field during your trip to Milwaukee. Attend a baseball game or simply enjoy the lively breweries while you're in the area.
See properties

Frequently asked questions

How much does a Southern Wisconsin vacation package cost?
Choose from any combination of flights, hotels and car rentals, and you can be vacationing in Southern Wisconsin from just CA $687. And the more you bundle, the more you save. Your dream escape has never been more affordable.
How do I get a cheap travel package to Southern Wisconsin?
Our Southern Wisconsin vacation packages promise plenty of savings for the savvy traveler. For the best deal, simply bundle your flights, hotels and activities into one neat package. But great bargains are only the start of your next awesome adventure. When you book with Expedia, and you'll have over 550 airlines and 1,000,000 hotels throughout the world to choose from. Whatever your style, there's a vacation package with your name on it.
Where should I stay in Southern Wisconsin?
To see popular sights like Milwaukee Art Museum and American Family Field, Milwaukee is the place to be. Lots of travelers also love visiting Appleton, home to Gardens of the Fox Cities and Hearthstone Historic House Museum. If time is on your side, why not visit both cities?
What are the top hotels in Southern Wisconsin?
When it comes to hotels in Milwaukee, Potawatomi Hotel & Casino and Best Western Plus Milwaukee Airport Hotel & Conference Ctr are among the favorites. If you're also staying in Wisconsin Dells, Inn of the Pines and Silver Spruce Resort are waiting to welcome you.
How far in advance should I book my Southern Wisconsin vacation?
Savvy travelers often book early. You can usually start comparing international fares on Expedia up to a year before your intended flight. If you're late to book, don't despair. Cheap prices sometimes occur just weeks before departure.
What does an Expedia Southern Wisconsin travel package include?
From hotels and flights to car rentals, Expedia can help you put together a Southern Wisconsin package that works for you. Heading away for a few weeks? Check out a flight, rental car and hotel bundle. If you can only squeeze in a quick getaway, a flight and hotel deal could be more your style. Tours and activities can be added once you've made your booking. Our packages make it simple to save and plan.
What should I know before booking a Southern Wisconsin travel package?
So many places to travel to, so many things to do. With a travel package, you can cross more of them off your list. Combine your flights, rental cars and hotels and see how much you save.
If I'm not able to travel, can I cancel my Southern Wisconsin vacation package?
Yes, you can cancel your Southern Wisconsin booking if your travel plans have changed. Whether you'll incur a fee or not depends on your airline, hotel or car rental company. You may be able to cancel or change free of charge if you booked in the last 24 hours. Visit our Customer Service Portal to find out more.

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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.