Book Exclusive Wisconsin Vacation Packages

Choose one or more items to build your trip:

Search vacation packages deals in Wisconsin's top destinations

Milwaukee Art Museum which includes art and modern architecture

Milwaukee

Vacations
Milwaukee

Wisconsin flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was CA $1,127, price is now CA $704 per person
CA $704
per person
Mar 5 - Mar 10
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $2,966, price is now CA $1,868 per person
CA $1,868
per person
Mar 1 - Mar 7
found 5 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,785, price is now CA $1,181 per person
CA $1,181
per person
Mar 1 - Mar 7
found 5 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,720, price is now CA $1,140 per person
CA $1,140
per person
Mar 1 - Mar 7
found 5 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Price was CA $3,344, price is now CA $2,223 per person
CA $2,223
per person
Mar 1 - Mar 7
found 5 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Top Wisconsin hotels deals

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
424 E Wisconsin Ave Milwaukee WI
Free cancellation
Reserve now, pay when you stay
The price is CA $210 per night
CA $210
CA $248 total
Jan 9 - Jan 10, 2026
includes taxes & fees
Book a stay at this luxury hotel in Milwaukee. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Fiserv Forum and Harley-Davidson Museum are located nearby.
Pool
Spa
Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
139 E Kilbourn Ave Milwaukee WI
Free cancellation
Reserve now, pay when you stay
The price is CA $177 per night
CA $177
CA $208 total
Dec 28 - Dec 29
includes taxes & fees
Stay at this hotel in Milwaukee. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Fiserv Forum and Harley-Davidson Museum are located nearby.
Pet-friendly
Free WiFi
The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

3.5 out of 5
1 W Dayton St Madison WI
Free cancellation
Reserve now, pay when you stay
The price is CA $206 per night
CA $206
CA $238 total
Dec 25 - Dec 26
includes taxes & fees
Book a stay at this luxury hotel in Madison. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast and the pool in our reviews. Popular attractions Camp Randall Stadium and Alliant Energy Center are located nearby.
Pool
Hot tub
Polynesian Hotel & Suites Wisconsin Dells/Lake Delton

Polynesian Hotel & Suites Wisconsin Dells/Lake Delton

3 out of 5
857 N Frontage Rd Wisconsin Dells WI
The price is CA $73 per night
CA $73
CA $110 total
Dec 28 - Dec 29
includes taxes & fees
Book a stay at this family-friendly hotel in Wisconsin Dells. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Kalahari Indoor Waterpark and Mt. Olympus Water and Theme Park are located nearby.
Pool
Pet-friendly
DoubleTree by Hilton Madison East

DoubleTree by Hilton Madison East

4 out of 5
4402 E Washington Ave Madison WI
Free cancellation
Reserve now, pay when you stay
The price is CA $146 per night
CA $146
CA $169 total
Dec 28 - Dec 29
includes taxes & fees
Book a stay at this business-friendly hotel in Madison. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions East Towne Mall and Olbrich Botanical Gardens are located nearby.
Pool
Pet-friendly
Grand Marquis Waterpark Hotel & Suites

Grand Marquis Waterpark Hotel & Suites

2.5 out of 5
840 Wisconsin Dells Parkway South Wisconsin Dells WI
Free cancellation
Reserve now, pay when you stay
Get rates
Book a stay at this family-friendly hotel in Wisconsin Dells. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Kalahari Indoor Waterpark and Noah's Ark Waterpark are located nearby.
Pool
Parking included
Don't see what you're looking for?
See all available properties in Wisconsin
View all properties
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

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.

University of Wisconsin-Madison
Lambeau Field

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.

Lambeau Field
Granite Peak Ski Area

Granite Peak Ski Area

Hit the slopes in Rib Mountain with a visit to Granite Peak Ski Area. Attend a sporting event while you're in the area, or simply enjoy its local cheese shops.

Granite Peak Ski Area

Photos of local treasures

Browse Wisconsin vacation photos for more inspiration

Milwaukee Art Museum
Photo provided by NC Tourism - Bill Russ
Photo provided by NC Tourism - Bill Russ
Milwaukee Art Museum which includes art and modern architecture
Discovery World featuring modern architecture
Photo provided by NC Tourism - Bill Russ
Photo provided by NC Tourism - Bill Russ

Frequently asked questions

How much are vacation packages to Wisconsin?
Your vacation dreams can be realized in Wisconsin from as little as CA $704. Packages include flights and hotels, so organizing everything should be easy as pie. All you'll have to concentrate on is what amazing attraction you'll head to first.
Where can I get the best vacation package deals for Wisconsin?
You can't beat Travelocity when it comes to putting together your Wisconsin package deal. There are at least 400 air carriers and 1,000,000 properties around the world to select from. Secure your trip now and get ready to tick another amazing destination off your bucket list.
Why should I purchase my Wisconsin vacation package via Travelocity?
We've got 24/7 customer support, first-rate service and a Price Match Guarantee. Life is all about the journey — and we have amazing destinations for you to journey to all over the world. Wander with us and make your hip pocket happy.
Will I save money on my Wisconsin car rental if I combine it with hotels and flights?
You sure can with our Wisconsin vacation packages. With one of these, there are plenty of ways to stretch your budget further. Combine any two or more car, flight, hotel and tour bookings and watch your savings pile up. With your own set of wheels, all the landmarks in and around Wisconsin are an unforgettable road trip away.
Which airport is best for Wisconsin?
Dane County Regional Airport (MSN), Appleton Intl. Airport (ATW) and Austin Straubel Intl. Airport (GRB) are the most popular airports for people jetting to and from Wisconsin.
What is there to do in Wisconsin?
Wisconsin has hidden surprises around every turn, but make sure you get to Gardens of the Fox Cities and University of Wisconsin-Madison during your stay. These attractions should be on your to-do list.