Book Exclusive Wisconsin Vacation Packages
Search vacation packages deals in Wisconsin's top destinations
Milwaukee
Vacations
Wisconsin flight + hotel packages
Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was CA $999, price is now CA $677 per person
CA $677
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) 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
Downtown Chicago
Price was CA $1,956, price is now CA $1,265 per person
CA $1,265
per person
Mar 2 - Mar 6
found 1 day 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.
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was CA $1,103, price is now CA $718 per person
CA $718
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,088, price is now CA $721 per person
CA $721
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Pendry Chicago
Downtown Chicago
Price was CA $1,311, price is now CA $881 per person
CA $881
per person
Mar 2 - Mar 6
found 1 day 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.
Top Wisconsin hotels deals
The Pfister Hotel
424 E Wisconsin Ave Milwaukee WI
Free cancellation
Reserve now, pay when you stay
The price is CA $209 per night
CA $209
CA $247 total
Jan 11 - Jan 12, 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
139 E Kilbourn Ave Milwaukee WI
Free cancellation
Reserve now, pay when you stay
The price is CA $176 per night
CA $176
CA $208 total
Dec 29 - Dec 30
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
1 W Dayton St Madison WI
Free cancellation
Reserve now, pay when you stay
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
857 N Frontage Rd Wisconsin Dells WI
The price is CA $73 per night
CA $73
CA $109 total
Dec 30 - Dec 31
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
4402 E Washington Ave Madison WI
Free cancellation
Reserve now, pay when you stay
The price is CA $145 per night
CA $145
CA $168 total
Dec 25 - Dec 26
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
840 Wisconsin Dells Parkway South Wisconsin Dells WI
Free cancellation
Reserve now, pay when you stay
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
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.
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.
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.
Photos of local treasures
Browse Wisconsin vacation photos for more inspiration
