Southwest Wisconsin Vacation Packages 2025/2026 from $173

Southwest Wisconsin flight + hotel vacation packages

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

theWit Chicago, a Hilton Hotel

Downtown Chicago

Save 100% on your flight

$173

per person

Jan 22 - Jan 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, express check-in, and valet parking. Limo/town car service, WiFi in public areas, and express check-out are also on offer.

Pendry Chicago

Downtown Chicago

Save 100% on your flight

$319

per person

Jan 13 - Jan 17

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.

The Talbott, Autograph Collection

Downtown Chicago

Save 100% on your flight

$187

per person

Feb 6 - Feb 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 business center, free WiFi in public areas, and valet parking. Dry cleaning, luggage storage, and wedding services are also on offer.

The Emily Hotel

Downtown Chicago

Save 100% on your flight

$303

per person

Jan 22 - Jan 26

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.

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$287

per person

Feb 6 - Feb 9

found 1 day ago

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 Southwest Wisconsin hotels deals

The Madison Concourse Hotel and Governor's Club

1 W Dayton St, Madison, WI

$139 nightly

$161 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

Polynesian Hotel & Suites Wisconsin Dells/Lake Delton

857 N Frontage Rd, Wisconsin Dells, WI

$77 nightly

$86 total

Nov 21 - Nov 22

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

avid Hotel Wisconsin Dells – Lake Delton by IHG

1273 Kalahari Drive, Baraboo, WI

Free Cancellation

$89 nightly

$100 total

Nov 16 - Nov 17

Total with taxes and fees

This hotel features free WiFi in public areas, a computer station, and laundry facilities. Enjoy the free continental breakfast each morning. Staff at the 24-hour front desk can provide around-the-clock assistance.

Mt. Olympus Water & Theme Park Resort

655 N. Frontage Road, Wisconsin Dells, WI

Free Cancellation

Reserve now, pay when you stay

$55 nightly

$62 total

Nov 12 - Nov 13

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.

Best Western Plus InnTowner Madison

2424 University Avenue, Madison, WI

Free Cancellation

Reserve now, pay when you stay

$117 nightly

$135 total

Nov 16 - Nov 17

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and free perks like buffet breakfast and free self parking. Enjoy the hot tub and conveniences like a 24-hour front desk and laundry facilities.

Pool

Hot Tub

Grand Marquis Waterpark Hotel & Suites

840 Wisconsin Dells Parkway South, Wisconsin Dells, WI

Get rates

Free water park access and an indoor pool are featured at this smoke-free hotel. There's fun for all ages with a children's pool and a waterslide, and families will appreciate the onsite laundry facilities. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi.

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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

4.5/5(872 reviews)

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

4/5(146 reviews)

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.

Top Secret

3.5/5(178 reviews)

Enjoy a stop at Top Secret, an entertaining place to visit in Wisconsin Dells. Stroll along the riverfront in this family-friendly area, or check out its top-notch restaurants.

Frequently asked questions

How much are vacation packages to Southwest Wisconsin?

Vacation packages, which include hotels and flights in Southwest Wisconsin, start from $173. 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.