Southern Wisconsin Vacation Packages 2026 from $399

Southern Wisconsin flight + hotel vacation packages

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

Pendry Chicago

Downtown Chicago

$399

per person

Mar 13 - Mar 15

found 22 hours ago

Roundtrip flight included

Charlotte (CLT) to Chicago (ORD)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$472

per person

Mar 13 - Mar 15

found 22 hours ago

Roundtrip flight included

Charlotte (CLT) 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.

Swissotel - Chicago

Downtown Chicago

Save 100% on your flight

$402

per person

Feb 13 - Feb 17

found 1 day ago

Roundtrip flight included

Charlotte (CLT) to Chicago (ORD)

This hotel features 2 bars/lounges and a 24-hour gym. Traveling on business? Take advantage of the business center, express check-in, and valet parking. A restaurant, a 24-hour front desk, and laundry facilities are also provided.

The Emily Hotel

Downtown Chicago

Save 100% on your flight

$439

per person

Mar 13 - Mar 15

found 22 hours ago

Roundtrip flight included

Charlotte (CLT) 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.

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

$638

per person

Feb 4 - Feb 7

found 1 day ago

Roundtrip non-stop flight included

Charlotte (CLT) 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.

Top Southern Wisconsin hotels deals

The Pfister Hotel

424 E Wisconsin Ave Milwaukee WI

Free Cancellation

Reserve now, pay when you stay

$169 nightly

$199 total

Jan 13 - Jan 14, 2026

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

Saint Kate - The Arts Hotel

139 E Kilbourn Ave Milwaukee WI

Free Cancellation

Reserve now, pay when you stay

$148 nightly

$174 total

Jan 18 - Jan 19, 2026

Total with taxes and fees

This smoke-free hotel's 3 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. WiFi in public areas is free. Valet parking, a coffee shop, and express check-out are also offered.

Pet friendly

Free WiFi

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

Dec 28 - Dec 29

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

Polynesian Hotel & Suites Wisconsin Dells/Lake Delton

857 N Frontage Rd Wisconsin Dells WI

$77 nightly

$86 total

Dec 30 - Dec 31

Total with taxes and fees

This hotel features an indoor pool and a lazy river. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. Staff at the 24-hour front desk can provide around-the-clock assistance.

Pool

Pet friendly

Crowne Plaza Milwaukee Airport by IHG

6401 S 13th Street Milwaukee WI

Free Cancellation

$76 nightly

$90 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

This hotel features an indoor pool, a hot tub, and a restaurant. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and free airport shuttle. There's a gym on site, and a 24-hour front desk and a snack bar/deli are also provided.

Pool

Hot Tub

DoubleTree by Hilton Madison East

4402 E Washington Ave Madison WI

Free Cancellation

Reserve now, pay when you stay

$106 nightly

$122 total

Dec 25 - Dec 26

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 gym and perks like free self parking.

Pool

Pet friendly

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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

Bring the kids to Mt. Olympus Water and Theme Park and have a fun-filled day at this amusement park in Wisconsin Dells. Stroll along the area's riverfront 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 $399. 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.