Southern Wisconsin Vacation Packages 2026 from $509

Southern Wisconsin flight + hotel vacation packages

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

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$509

per person

Jan 22 - Jan 25

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 Fulton Market

Downtown Chicago

$617

per person

Jan 23 - Jan 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a gym and a seasonal outdoor pool. WiFi in public areas is free. Self parking, a business center, and a picnic area are also offered.

The Emily Hotel

Downtown Chicago

$812

per person

Jan 23 - Jan 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A restaurant and a 24-hour gym are featured at this hotel. 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.

Villa Christina

Greater Grand Crossing

$514

per person

Jan 28 - Jan 31

found 19 hours ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. Laundry facilities are provided for your convenience.

Eurostars Magnificent Mile

Downtown Chicago

Save 100% on your flight

$565

per person

Jan 22 - Jan 25

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A full-service spa and a gym are featured at this boutique hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a sauna on site, and a 24-hour front desk and express check-out are also provided.

Top Southern Wisconsin hotels deals

The Madison Concourse Hotel and Governor's Club

1 W Dayton St Madison WI

Free Cancellation

Reserve now, pay when you stay

$127 nightly

$146 total

Nov 16 - Nov 17

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

AmericInn by Wyndham Brookfield

16865 W Bluemound Rd Brookfield WI

Free Cancellation

Reserve now, pay when you stay

$80 nightly

$93 total

Nov 15 - Nov 16

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.

Pool

Breakfast included

Hyatt Regency Milwaukee

333 W Kilbourn Ave Milwaukee WI

Free Cancellation

Reserve now, pay when you stay

$79 nightly

$93 total

Nov 23 - Nov 24

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.

Pet friendly

Free WiFi

Sheraton Milwaukee Brookfield Hotel

375 S Moorland Rd Brookfield WI

Free Cancellation

Reserve now, pay when you stay

$87 nightly

$100 total

Nov 22 - Nov 23

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

Motel 6 Madison, WI - East

4202 E Towne Blvd Madison WI

Free Cancellation

$53 nightly

$61 total

Dec 4 - Dec 5

Total with taxes and fees

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Express check-in, express check-out, and laundry facilities are also on offer.

Pet friendly

Parking included

Natura Vue Resort & Boathouse

1015 River Rd Wisconsin Dells WI

$85 nightly

$95 total

Nov 15 - Nov 16

Total with taxes and fees

A marina and an indoor pool are featured at this smoke-free hotel. Enjoy a day at the beach water skiing, or relax with sun loungers. Enjoy a meal from the restaurant and perks like free WiFi.

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.

Stay near popular Southern Wisconsin attractions

A coastal landscape with autumn foliage, a beach, and a building.

Kalahari Indoor Waterpark

8.8/10 (445 reviews)

Have a fun-filled day at Kalahari Indoor Waterpark and see why people love this amusement park in Baraboo. Stroll along the riverfront or experience the entertainment choices in this family-friendly area.

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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 $509. 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.