Vacation Packages to Wisconsin for 2026
Wisconsin Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Sleep Inn & Suites Green Bay South
Price was $753, price is now $558 per person
$558
per person
Mar 16 - Mar 23
found 1 day ago
Roundtrip non-stop flight included
Orlando (ORL) to Green Bay (GRB)
Book a stay at this business-friendly hotel in De Pere. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Lambeau Field and Oneida Casino are located nearby.
Tundra Lodge
Save 100% on your flight
Price was $1,277, price is now $749 per person
$749
per person
Mar 16 - Mar 23
found 1 day ago
Roundtrip non-stop flight included
Orlando (ORL) to Green Bay (GRB)
Book a stay at this family-friendly hotel in Green Bay. Enjoy free WiFi, an outdoor pool, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Lambeau Field and Resch Center are located nearby.
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $897, price is now $572 per person
$572
per person
Mar 22 - Mar 27
found 15 hours ago
Roundtrip flight included
Norfolk (ORF) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,822, price is now $1,175 per person
$1,175
per person
Mar 22 - Mar 27
found 1 day ago
Roundtrip flight included
Norfolk (ORF) 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.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was $1,001, price is now $675 per person
$675
per person
Mar 22 - Mar 27
found 1 day ago
Roundtrip flight included
Norfolk (ORF) 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.
JW Marriott Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,391, price is now $972 per person
$972
per person
Mar 22 - Mar 27
found 1 day ago
Roundtrip flight included
Norfolk (ORF) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Top Hotel Deals
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 ...
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 ...
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 ...
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 ...
Baymont by Wyndham Madison West/Middleton WI West
8102 Excelsior Dr Madison WI
98.57 km from city center
Book a stay at this family-friendly hotel in Madison. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Great Wolf Lodge Wisconsin Dells
1400 Great Wolf Dr Baraboo WI
83.32 km from city center
Book a stay at this family-friendly resort in Baraboo. Enjoy 6 indoor pools, 3 restaurants, and 2 hot tubs. Our guests praise the helpful staff in our reviews. ...
Mt. Olympus Water & Theme Park Resort
655 N. Frontage Road Wisconsin Dells WI
83.02 km from city center
Book a stay at this family-friendly resort in Wisconsin Dells. Enjoy an outdoor pool, free water park access, and parking (surcharge). Our guests praise 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 ...
Oneida Casino Hotel
2040 Airport Dr Green Bay WI
95.42 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 ...
Polynesian Hotel & Suites Wisconsin Dells/Lake Delton
857 N Frontage Rd Wisconsin Dells WI
83.47 km from city center
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 ...
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 ...
Motel 6 Milwaukee, WI - Glendale
5485 N Port Washington Rd Milwaukee WI
102.26 km from city center
Stay at this motel in Milwaukee. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
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.
Wed, Mar 25 - Tue, Apr 14
DEN
Denver
MSP
Minneapolis
$66 Roundtrip, found 3 days ago
$66
Roundtrip
found 3 days ago
Sun, Aug 9 - Sun, Aug 16
ATL
Atlanta
MSP
Minneapolis
$157 Roundtrip, found 2 days ago
$157
Roundtrip
found 2 days ago
Tue, Mar 24 - Wed, Apr 1
EWR
New York
MSN
Madison
$229 Roundtrip, found 1 day ago
$229
Roundtrip
found 1 day ago
Tue, Feb 24 - Tue, Mar 3
DEN
Denver
MSN
Madison
$229 Roundtrip, found 1 day ago
$229
Roundtrip
found 1 day ago
Tue, May 19 - Mon, May 25
SEA
Seattle
MKE
Milwaukee
$242 Roundtrip, found 1 day ago
$242
Roundtrip
found 1 day ago