Vacation Packages to Wisconsin for 2026
Wisconsin Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was $1,054, price is now $791 per person
$791
per person
Jul 21 - Jul 25
found 15 hours ago
Roundtrip non-stop flight included
Palm Springs (PSP) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,407, price is now $932 per person
$932
per person
Jul 21 - Jul 25
found 15 hours ago
Roundtrip non-stop flight included
Palm Springs (PSP) 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.
Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,283, price is now $870 per person
$870
per person
Jul 21 - Jul 25
found 15 hours ago
Roundtrip non-stop flight included
Palm Springs (PSP) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,419, price is now $985 per person
$985
per person
Jul 21 - Jul 25
found 15 hours ago
Roundtrip non-stop flight included
Palm Springs (PSP) 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.
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,461, price is now $1,069 per person
$1,069
per person
Jul 21 - Jul 25
found 15 hours ago
Roundtrip non-stop flight included
Palm Springs (PSP) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. 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 Chicago Riverwalk and Michigan Avenue are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,451, price is now $1,062 per person
$1,062
per person
Jul 21 - Jul 25
found 15 hours ago
Roundtrip non-stop flight included
Palm Springs (PSP) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue 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 ...
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 ...
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 ...
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 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 ...
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 free WiFi, 6 indoor pools, and 3 restaurants. Our guests praise the helpful staff in our reviews. ...
Harbor Shores on Lake Geneva
300 Wrigley Dr Lake Geneva WI
136.01 km from city center
Book a stay at this family-friendly hotel in Lake Geneva. Enjoy free WiFi, free parking, and room service. Our guests praise the pool and the helpful staff 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 ...
Sheraton Milwaukee Brookfield Hotel
375 S Moorland Rd Brookfield WI
100.53 km from city center
Book a stay at this golf hotel in Brookfield. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in ...
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 ...
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 ...
Natura Treescape Resort
400 County Road A Wisconsin Dells WI
82.13 km from city center
Book a stay at this beach hotel in Wisconsin Dells. Enjoy free WiFi, 2 indoor pools, and a private beach. Our guests praise the pool and the helpful staff in ...
Crowne Plaza Milwaukee Airport by IHG
6401 S 13th Street Milwaukee WI
117.75 km from city center
Book a stay at this business-friendly hotel in Milwaukee. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
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, Oct 7 - Thu, Oct 22
DEN
Denver
MSP
Minneapolis
$148 Roundtrip, found 23 hours ago
$148
Roundtrip
found 23 hours ago
Mon, Sep 14 - Tue, Sep 29
PHX
Phoenix
MSP
Minneapolis
$227 Roundtrip, found 19 hours ago
$227
Roundtrip
found 19 hours ago
Thu, Sep 17 - Thu, Sep 24
DEN
Denver
RFD
Rockford
$236 Roundtrip, found 5 days ago
$236
Roundtrip
found 5 days ago
Tue, Jun 23 - Tue, Jun 30
DEN
Denver
MSN
Madison
$269 Roundtrip, found 1 day ago
$269
Roundtrip
found 1 day ago
Wed, Sep 16 - Tue, Sep 22
PHX
Phoenix
MKE
Milwaukee
$279 Roundtrip, found 3 days ago
$279
Roundtrip
found 3 days ago