Vacation Packages to Wisconsin for 2025
Wisconsin Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Arlo Chicago
Downtown Chicago
Price was $999, price is now $696 per person
$696
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
The Ritz-Carlton, Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,874, price is now $1,132 per person
$1,132
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,927, price is now $1,240 per person
$1,240
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
New York (JFK) 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.
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $1,197, price is now $783 per person
$783
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions United Center and Chicago Riverwalk are located nearby.
Pendry Chicago
Downtown Chicago
Price was $1,081, price is now $715 per person
$715
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
New York (JFK) 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.
Eurostars Magnificent Mile
Downtown Chicago
Price was $1,034, price is now $739 per person
$739
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Top Hotel Deals
The Madison Concourse Hotel and Governor's Club
1 W Dayton St Madison WI
92.4 km from city center
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 ...
Timber Ridge Lodge and Waterpark
7020 Grand Geneva Way Lake Geneva WI
135.24 km from city center
Book a stay at this spa aparthotel in Lake Geneva. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
The Pfister Hotel
424 E Wisconsin Ave Milwaukee WI
109.29 km from city center
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 ...
Hilton Milwaukee
509 W Wisconsin Ave Milwaukee WI
108.7 km from city center
Book a stay at this luxury hotel in Milwaukee. Enjoy free WiFi, 2 restaurants, and 3 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
Oneida Casino Hotel
2040 Airport Dr Green Bay WI
95.37 km from city center
Book a stay at this business-friendly hotel in Green Bay. Enjoy free WiFi, free parking, and 4 restaurants. Our guests praise the helpful staff and the clean ...
Hyatt Regency Milwaukee
333 W Kilbourn Ave Milwaukee WI
108.62 km from city center
Book a stay at this business-friendly hotel in Milwaukee. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the ...
Drury Plaza Hotel Milwaukee Downtown
700 N. Water Street Milwaukee WI
109.15 km from city center
Book a stay at this business-friendly hotel in Milwaukee. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and ...
Saint Kate - The Arts Hotel
139 E Kilbourn Ave Milwaukee WI
108.78 km from city center
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 ...
Potawatomi Hotel & Casino
1611 West Canal Street Milwaukee WI
108.43 km from city center
Book a stay at this luxury hotel in Milwaukee. Enjoy free WiFi, free parking, and 7 restaurants. Our guests praise the helpful staff and the clean rooms in our ...
The Iron Horse Hotel
500 W Florida Street Milwaukee WI
109.71 km from city center
Book a stay at this boutique hotel in Milwaukee. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Ambassador Hotel Milwaukee, Trademark Collection by Wyndham
2308 W Wisconsin Ave Milwaukee WI
107.41 km from city center
Stay at this hotel in Milwaukee. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular ...
avid Hotel Wisconsin Dells – Lake Delton by IHG
1273 Kalahari Drive Baraboo WI
82.94 km from city center
Book a stay at this business-friendly hotel in Baraboo. Enjoy free breakfast, free WiFi, and a 24-hour front desk. Our guests praise the helpful staff in our ...
Country Inn & Suites by Radisson, Milwaukee West (Brookfield), WI
1250 S Moorland Rd Brookfield WI
101.31 km from city center
Book a stay at this business-friendly hotel in Brookfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Tue, Jan 6 - Mon, Jan 12
DEN
Denver
MSP
Minneapolis
$68 Roundtrip, found 2 days ago
$68
Roundtrip
found 2 days ago
Thu, Dec 18 - Fri, Dec 19
DEN
Denver
MSP
Minneapolis
$127 Roundtrip, found 3 days ago
$127
Roundtrip
found 3 days ago
Sat, Jan 3 - Tue, Jan 13
DEN
Denver
MSP
Minneapolis
$170 Roundtrip, found 2 days ago
$170
Roundtrip
found 2 days ago
Wed, Mar 4 - Sun, Mar 8
SEA
Seattle
MKE
Milwaukee
$207 Roundtrip, just found
$207
Roundtrip
just found
Mon, Mar 2 - Mon, Mar 9
SEA
Seattle
MKE
Milwaukee
$217 Roundtrip, just found
$217
Roundtrip
just found