Southern Wisconsin Vacation Packages 2025/2026 from $231

Southern Wisconsin flight + hotel vacation packages

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

Illinois Beach Hotel

Save 100% on your flight

$231

per person

Nov 11 - Nov 15

found 8 hours ago

Roundtrip flight included

New Orleans (MSY) to Chicago (ORD)

A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area is provided and the front desk is staffed around-the-clock.

Hampton Inn & Suites Chicago Medical District UIC

Near West Side

$528

per person

Oct 22 - Oct 29

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the free full breakfast each morning.

The Emily Hotel

Downtown Chicago

$1,075

per person

Oct 22 - Oct 29

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$425

per person

Oct 17 - Oct 19

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.

The Langham, Chicago

Downtown Chicago

Save 100% on your flight

$1,578

per person

Oct 22 - Oct 29

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the gym, bar/lounge, and laundry facilities.

Top Southern Wisconsin hotels deals

Mt. Olympus Water & Theme Park Resort

655 N. Frontage Road, Wisconsin Dells, WI

Free Cancellation

Reserve now, pay when you stay

$65 nightly

$73 total

Sep 10 - Sep 11

Total with taxes and fees

Free water park access and a lazy river are featured at this smoke-free resort. Bring the family and enjoy the children's pool, waterslide, and playground. There's a restaurant and a bar/lounge for dining and drinks, and also a seasonal outdoor pool on site.

Pool

Restaurant

The Madison Concourse Hotel and Governor's Club

1 W Dayton St, Madison, WI

$139 nightly

$161 total

Sep 14 - Sep 15

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. There's a gym on site, and a 24-hour front desk and a coffee shop are also provided.

Pool

Hot Tub

Harbor Shores on Lake Geneva

300 Wrigley Dr, Lake Geneva, WI

$144 nightly

$164 total

Sep 21 - Sep 22

Total with taxes and fees

This hotel features an outdoor pool, an indoor pool, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.

Pool

Parking included

The Pfister Hotel

424 E Wisconsin Ave, Milwaukee, WI

Free Cancellation

Reserve now, pay when you stay

$205 nightly

$242 total

Oct 1 - Oct 2

Total with taxes and fees

A full-service spa, 2 restaurants, and an indoor pool are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Enjoy the 24-hour gym and visit the 3 bars/lounges and poolside bar for drinks.

Pool

Spa

Baymont by Wyndham Madison West/Middleton WI West

8102 Excelsior Dr, Madison, WI

Free Cancellation

Reserve now, pay when you stay

$61 nightly

$71 total

Sep 11 - Sep 12

Total with taxes and fees

This hotel features an indoor pool and a gym. Families will appreciate the arcade/game room and barbecue grills. Enjoy the hot tub and free perks like continental breakfast and free self parking.

Pool

Hot Tub

Timber Ridge Lodge and Waterpark

7020 Grand Geneva Way, Lake Geneva, WI

Free Cancellation

Reserve now, pay when you stay

$187 nightly

$209 total

Oct 8 - Oct 9

Total with taxes and fees

This smoke-free aparthotel features a golf course, free water park access, and a full-service spa. Take advantage of ski lessons, ski rentals and ski storage on site, and enjoy downhill skiing. Bring the family and enjoy the lazy river, mini golf, and kid-friendly dining.

Pool

Hot Tub

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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.

Popular places to visit

University of Wisconsin-Madison

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.

Mt. Olympus Water and Theme Park

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 lakeside or experience its entertainment choices.

Harley-Davidson Museum

Delve into the history of one of the world’s most famous motorcycle brands via interactive exhibits, photo galleries, workshops and behind-the-scenes tours.

Frequently asked questions

How much are vacation packages to Southern Wisconsin?

Prepare to be pleasantly surprised — you can recharge your batteries in Southern Wisconsin for just $231. Allow Travelocity to save you time and money with our excellent vacation packages. With flights, hotels and tours all ready to go, why wait any longer?

Where can I get the best vacation package deals for Southern Wisconsin?

With at least 400 airlines and 1,000,000 properties all over the world, it's hard to go past Travelocity. Make the most of our comprehensive range and create your dream Southern Wisconsin package deal. Isn't it great when trip planning is that easy?

Why should I book my Southern Wisconsin vacation bundle via Travelocity?

We have experiences and destinations for every type of traveler, top-quality service and 24/7 support. In addition to that, we'll match any cheaper price you discover with our Price Match Guarantee.

Can I save money on my Southern Wisconsin car rental if I combine it with my hotel or flight?

Combining your bookings into a Southern Wisconsin vacation package will leave you with some serious savings. Bundle a flight and car; a flight, hotel and car; or a car and hotel. There's no better way to discover the greater Southern Wisconsin area than with your own rental car. You can also add tours and experiences to your Travelocity package.

Which airport is best for Southern Wisconsin?

The top airports for Southern Wisconsin are General Mitchell Intl. Airport (MKE) and Dane County Regional Airport (MSN).

What is there to do in Southern Wisconsin?

Southern Wisconsin boasts hidden gems around every turn, however ensure you get to Gardens of the Fox Cities and American Family Field while you're here. These attractions are a must-see.