Southwest Wisconsin Vacation Packages 2025/2026 from $484

Southwest Wisconsin flight + hotel vacation packages

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

Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

Save 100% on your flight

$484

per person

Sep 24 - Sep 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 24-hour business center, free WiFi in public areas, and valet parking. A terrace, a snack bar/deli, and a free grocery shopping service are also on offer.

Trump International Hotel & Tower Chicago

Downtown Chicago

$1,098

per person

Sep 24 - Sep 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. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.

Pendry Chicago

Downtown Chicago

Save 100% on your flight

$814

per person

Sep 24 - Sep 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. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.

Bluegreen Vacations Hotel Blake, Ascend Resort Collection

Downtown Chicago

Save 100% on your flight

$658

per person

Oct 2 - Oct 9

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 24-hour business center, free WiFi in public areas, and valet parking. A coffee shop, limo/town car service, and express check-out are also on offer.

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

$793

per person

Sep 24 - Sep 29

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A full-service spa, 2 restaurants, and a gym are all featured at this luxury hotel. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi. A business center, a terrace, and dry cleaning are also on offer.

Top Southwest Wisconsin hotels deals

Mt. Olympus Water & Theme Park Resort

655 N. Frontage Road, Wisconsin Dells, WI

Free Cancellation

Reserve now, pay when you stay

$40 nightly

$45 total

Sep 1 - Sep 2

Total includes 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

Free Cancellation

Reserve now, pay when you stay

$139 nightly

$161 total

Aug 31 - Sep 1

Total includes 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

Days Inn & Suites by Wyndham Wisconsin Dells

2504 Wisconsin Dells Parkway, Wisconsin Dells, WI

Free Cancellation

Reserve now, pay when you stay

$48 nightly

$54 total

Sep 8 - Sep 9

Total includes taxes and fees

This hotel features an indoor pool and a gym. Families will appreciate the mini golf and onsite laundry facilities. Enjoy the hot tub and free perks like continental breakfast and free self parking.

Pool

Hot Tub

Natura Treescape Resort

400 County Road A, Wisconsin Dells, WI

$65 nightly

$73 total

Sep 1 - Sep 2

Total includes taxes and fees

A private beach, 2 indoor pools, and 2 hot tubs are all featured at this smoke-free hotel. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the seasonal outdoor pool and perks like free WiFi.

On private beach

Pool

The VUE Boutique Hotel & Boathouse

1015 River Rd, Wisconsin Dells, WI

$65 nightly

$73 total

Sep 1 - Sep 2

Total includes 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

Polynesian Hotel & Suites Wisconsin Dells/Lake Delton

857 N Frontage Rd, Wisconsin Dells, WI

Get rates

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

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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 riverfront or experience its entertainment choices.

Devil's Lake

Commune with nature and explore the great outdoors at Devil's Lake during your travels in Baraboo. Discover the entertainment venues in this family-friendly area, or seek out its hiking trails.

Frequently asked questions

How much are vacation packages to Southwest Wisconsin?

Vacation packages, which include hotels and flights in Southwest Wisconsin, start from $484. Turn your travel dreams into reality and book your trip with Travelocity today.

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

There are terrific Southwest Wisconsin package deals waiting for you with Travelocity. Did you know we partner with as many as 400 airlines and 1,000,000 properties in all corners of the globe? Keep this in mind the next time you're ready to check another destination off the old bucket list.

Why should I purchase my Southwest Wisconsin vacation bundle with Travelocity?

We've got 24/7 customer support, excellent service and a Price Match Guarantee. Life is one big journey — and we have amazing destinations for you to journey to in all four corners of the globe. Roam with us and your wallet will thank you for it.

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

You can with our Southwest Wisconsin vacation packages. With one of these, there are lots of ways to make your travel budget go further. Bundle any two or more car, flight, hotel and tour bookings and see the savings start to pile up. With a rental car, all the popular attractions around Southwest Wisconsin are just a road trip away.

Which airport is best for Southwest Wisconsin?

Southwest Wisconsin has two main hubs — Dane County Regional Airport (MSN) and La Crosse Municipal Airport (LSE).

What is there to do in Southwest Wisconsin?

Southwest Wisconsin has hidden gems around every corner, but make sure you get to Mt. Olympus Water and Theme Park and The House on the Rock during your stay. These attractions are very popular with visitors to the region.