Vacation Packages to Wisconsin for 2026
Wisconsin Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $687, price is now $432 per person
$432
per person
Feb 4 - Feb 9
found 1 day ago
Roundtrip flight included
Denver (DEN) 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.
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $764, price is now $460 per person
$460
per person
Feb 4 - Feb 9
found 1 day ago
Roundtrip flight included
Denver (DEN) 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.
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $841, price is now $516 per person
$516
per person
Feb 4 - Feb 9
found 1 day ago
Roundtrip flight included
Denver (DEN) 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.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Save 100% on your flight
Price was $705, price is now $435 per person
$435
per person
Feb 4 - Feb 9
found 1 day ago
Roundtrip flight included
Denver (DEN) 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.
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $810, price is now $500 per person
$500
per person
Feb 4 - Feb 9
found 1 day ago
Roundtrip flight included
Denver (DEN) 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.
Palmer House a Hilton Hotel
Downtown Chicago
Save 100% on your flight
Price was $721, price is now $477 per person
$477
per person
Feb 4 - Feb 9
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and the clean rooms 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 ...
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 ...
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 ...
Hampton Inn & Suites Madison-West
483 Commerce Dr Madison WI
100.45 km from city center
Book a stay at this business-friendly hotel in Madison. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 27 - Tue, Feb 3
DEN
Denver
MSP
Minneapolis
$68 Roundtrip, found 5 days ago
$68
Roundtrip
found 5 days ago
Wed, Aug 5 - Sat, Aug 8
EWR
New York
MSP
Minneapolis
$187 Roundtrip, found 3 days ago
$187
Roundtrip
found 3 days ago
Thu, Dec 25 - Thu, Jan 1
PHX
Phoenix
MKE
Milwaukee
$231 Roundtrip, found 5 days ago
$231
Roundtrip
found 5 days ago
Wed, Jan 28 - Fri, Feb 27
LGA
New York
ATW
Appleton
$249 Roundtrip, found 6 days ago
$249
Roundtrip
found 6 days ago
Mon, Jan 26 - Sun, Feb 8
JFK
New York
ATW
Appleton
$274 Roundtrip, found 6 days ago
$274
Roundtrip
found 6 days ago