Southern Wisconsin Vacation Packages 2026 from $491

Southern Wisconsin flight + hotel vacation packages

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

The Talbott, Autograph Collection

Downtown Chicago

Save 100% on your flight

$491

per person

Nov 16 - Nov 19

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 business center, free WiFi in public areas, and valet parking. Dry cleaning, luggage storage, and wedding services are also on offer.

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

$851

per person

Nov 12 - Nov 15

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. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

Save 100% on your flight

$565

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features 3 restaurants, a bar/lounge, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A coffee shop, express check-out, and luggage storage are also on offer.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$653

per person

Nov 12 - Nov 15

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.

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$547

per person

Dec 19 - Dec 22

just found

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.

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

$53 nightly

$59 total

Oct 5 - Oct 6

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.

The Madison Concourse Hotel and Governor's Club

1 W Dayton St Madison WI

Free Cancellation

Reserve now, pay when you stay

$139 nightly

$161 total

Nov 1 - Nov 2

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

Free Cancellation

Reserve now, pay when you stay

$117 nightly

$133 total

Nov 1 - Nov 2

Total with taxes and fees

This smoke-free hotel includes 2 restaurants, an outdoor pool, and an indoor pool. Enjoy the gym and perks like free self parking and free WiFi. Relax with a drink at the bar/lounge and enjoy the sauna.

Pool

Parking included

Hyatt Regency Milwaukee

333 W Kilbourn Ave Milwaukee WI

Free Cancellation

Reserve now, pay when you stay

$93 nightly

$110 total

Oct 11 - Oct 12

Total with taxes and fees

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Self parking, a coffee shop, and a snack bar/deli are also offered.

Drury Plaza Hotel Milwaukee Downtown

700 N. Water Street Milwaukee WI

Free Cancellation

Reserve now, pay when you stay

$119 nightly

$140 total

Nov 1 - Nov 2

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 and free WiFi in public areas. Enjoy the 24-hour gym and free buffet breakfast each morning.

Timber Ridge Lodge and Waterpark

7020 Grand Geneva Way Lake Geneva WI

Free Cancellation

Reserve now, pay when you stay

$168 nightly

$187 total

Oct 20 - Oct 21

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

Don't see what you're looking for?

See all available properties in Southern Wisconsin

View all properties

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.

Stay near popular Southern Wisconsin attractions

A sign for Miller Park, home of the Milwaukee Brewers, with a baseball and stars.

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 are vacation packages to Southern Wisconsin?

Prepare to be pleasantly surprised — you can recharge your batteries in Southern Wisconsin for just $491. 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.