Wisconsin Vacation Packages & Trips 2025 from $253

Name: Days Inn & Suites by Wyndham Wisconsin Dells
Price range: CA $66
Rating: 7

Your Wisconsin Vacation

Our Wisconsin vacation packages provide an affordable, easy and engaging way to enjoy everything this destination has to offer. If it's distilleries and craft breweries and dining you're after, this is the place to come. With so much to explore on a trip to Wisconsin, it can be difficult to know where to start. Kick off your journey in Milwaukee at American Family Field and Wisconsin State Fair Park — two popular attractions here. Another city worthy of a spot on your itinerary is Madison. Be sure not to miss Camp Randall Stadium and Wisconsin State Capitol. Expedia has hotels, flights and all your other travel needs to help you put together your own customized Wisconsin vacation today.

Top vacation destinations in Wisconsin

Milwaukee Art Museum which includes art and modern architecture

Top Wisconsin Vacation Deals

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

The Emily Hotel

Downtown Chicago

per person

Oct 24 - Oct 27

found 21 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,159 reviews)

Food prices parking prices

Reviewed on Aug. 13, 2025

Park Hyatt Chicago

Downtown Chicago

per person

Oct 5 - Oct 11

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.6/10 Exceptional! (1,000 reviews)

Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on Aug. 10, 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

per person

Oct 2 - Oct 5

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,679 reviews)

It was totally worth the money as it had the best amenities, great views overlooking the city, and the river, staff was phenomenal, and couldn’t ask for more!

Reviewed on Aug. 15, 2025

Hilton Chicago

Downtown Chicago

per person

Sep 18 - Sep 24

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

8.4/10 Very Good! (2,048 reviews)

Our family loves to stay at the Hilton. It's close to many classic Chicago sites. You have a wonderful deep dish pizza around the corner. The staff are always friendly and efficient.

Reviewed on Aug. 15, 2025

The Langham, Chicago

Downtown Chicago

per person

Oct 5 - Oct 11

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.8/10 Exceptional! (1,004 reviews)

Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.

Reviewed on Aug. 12, 2025

Where to stay in Wisconsin

Find the best Wisconsin areas and neighborhoods for the activities you enjoy most. Learn more about Wisconsin

Downtown Milwaukee

Central business district with cultural, financial, and historical landmarks, Downtown Milwaukee offers shopping at The Shops of Grand Avenue, art galleries in the Historic Third Ward, high-end dining, and vibrant nightlife. Explore the Milwaukee Public Market and Riverwalk, or hop on the free streetcar system.

Wisconsin Hotel Deals

Mt. Olympus Water & Theme Park Resort

655 N. Frontage Road, Wisconsin Dells, WI

Fully refundableReserve now, pay when you stay

CA $55

CA $62 total

Sep 1 - Sep 2

includes taxes & fees

6.8/10 (2,341 reviews)

"All 10 of us adults and kids had such a great time. Every worker was so pleasant to be around. The Hotel Rome room was fantastic since I had 2 rooms and they adjoined each other. Price were pretty good for food and drinks. Had the rented table and umbrella - oh that was a big plus the extra money ..."

Reviewed on Aug. 12, 2025

Harbor Shores on Lake Geneva

300 Wrigley Dr, Lake Geneva, WI

Fully refundableReserve now, pay when you stay

CA $184

CA $236 total

Sep 11 - Sep 12

includes taxes & fees

9/10 Wonderful! (1,220 reviews)

"Wonderful AC. Relaxing pool time. Excellent location to lake, walking path, shopping, and restaurants."

Reviewed on Aug. 12, 2025

Days Inn & Suites by Wyndham Wisconsin Dells

2504 Wisconsin Dells Parkway, Wisconsin Dells, WI

Fully refundableReserve now, pay when you stay

CA $66

CA $74 total

Sep 1 - Sep 2

includes taxes & fees

7/10 Good! (1,502 reviews)

"Fast check in , friendly staff"

Reviewed on Aug. 14, 2025

See all 15,739 properties in Wisconsin

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.

Frequently asked questions

How much does a Wisconsin vacation package cost?

Starting from as low as CA $862, a package is your portal to low-cost travel. Custom make your Wisconsin adventure by choosing from our extensive range of flights, hotels and rental cars.

How do I get a cheap travel package to Wisconsin?

Bundling your flight and hotel with Expedia won't just save precious time — it'll save you cash too. A Wisconsin vacation package makes it easy to organize your dream adventure. With more than 550 airlines throughout the world to choose from, finding convenient flights that fit your busy schedule won't be an issue. Not only that, we've got over 1,000,000 properties globally to select from. Talk about choice! No matter who you are, Expedia puts the world within your reach.

Where should I stay in Wisconsin?

Milwaukee is a fantastic place to include in your itinerary. It's where you'll find impressive sights such as Milwaukee Art Museum and American Family Field. Madison also attracts many jetsetters eager to explore some of the best attractions in Wisconsin. Some of the best are University of Wisconsin-Madison and Camp Randall Stadium.

What are the top hotels in Wisconsin?

Potawatomi Hotel & Casino and Best Western Plus Milwaukee Airport Hotel & Conference Ctr know how to make their guests feel at home in Milwaukee. If your itinerary also includes Wisconsin Dells, take a look at Inn of the Pines and Silver Spruce Resort. Both are popular with travelers.

How far in advance should I book my Wisconsin vacation?

Savvy travelers will likely want to reserve their seats as early as possible. You can normally compare international fares on Expedia up to a year before your intended flight. If you're booking at the last minute, fear not. Low prices occasionally become available just weeks before departure dates.

What does an Expedia Wisconsin travel package include?

Expedia has all you need to arrange your Wisconsin getaway, but what your package looks like is totally up to you. Choose from a combination of hotels, flights and rental cars. Searching for some activities to fill in your time? Once you've made your booking, you can add them on too. No matter your style or budget, there's a package deal to match your needs.

What should I know before booking a Wisconsin travel package?

Discover deals to match your budget with an Expedia package. Flights, hotels, rental cars — we have everything you need to plan your break. You'll save a tidy sum just for bundling your bookings. Whether you're taking off on a ski trip or sunning yourself on a warm beach, your ideal vacation is only a few clicks away.

Can I choose my airline with a Wisconsin Expedia vacation package?

Yes, you sure can. We have more than 550 partner airlines globally, so go with the carrier that suits your needs.

If I'm not able to travel, can I cancel my Wisconsin vacation package?

Certainly, and we'll help you every step of the way. You may be able to cancel and rebook your Wisconsin vacation package for free if you booked in the last 24 hours. But you may incur a fee from your airline, hotel or car rental company if your booking is older than that. If life gets in the way of your vacation, look up our Customer Service Portal for more information.

Discover the most popular places to visit in Wisconsin

Lambeau Field

Catch an event at Lambeau Field during your trip to Green Bay. Amble around this family-friendly area's riverfront or attend a sporting event.

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.

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.

What to do in Wisconsin

Grohmann Museum at Milwaukee School of Engineering

Skip the Line: Museum Admission Ticket - Grohmann Museum

CA $7

per adult

Haunted Madison Capitol Building on Madison Ghosts Haunted Walking Tour

Madison Ghosts: Haunts, Spirits, and Poltergeists Walking Tour

CA $36

per adult

The Grand Walk: A Self-Guided Audio Tour through Milwaukee

CA $12

per adult

80% of travellers recommend

See all activities in Wisconsin

Other vacations you might like

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Wisconsin Vacation Packages

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Your Wisconsin Vacation

Top vacation destinations in Wisconsin

Milwaukee

Top Wisconsin Vacation Deals

The Emily Hotel

Park Hyatt Chicago

Trump International Hotel & Tower Chicago

Hilton Chicago

The Langham, Chicago

Where to stay in Wisconsin

Downtown Milwaukee

Wisconsin Hotel Deals

Mt. Olympus Water & Theme Park Resort

Harbor Shores on Lake Geneva

Days Inn & Suites by Wyndham Wisconsin Dells

Frequently asked questions

Discover the most popular places to visit in Wisconsin

Lambeau Field

Mt. Olympus Water and Theme Park

Harley-Davidson Museum

What to do in Wisconsin

Skip the Line: Museum Admission Ticket - Grohmann Museum

Madison Ghosts: Haunts, Spirits, and Poltergeists Walking Tour

The Grand Walk: A Self-Guided Audio Tour through Milwaukee

Other vacations you might like

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