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Old World Wisconsin Vacation Packages

Old World Wisconsin Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
Save 100% on your flight
per person
Feb 11 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) 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 helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
W Chicago - Lakeshore

W Chicago - Lakeshore

4.5 out of 5
per person
Feb 10 - Feb 16
found 13 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy breakfast (surcharge), room service, and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Navy Pier are located nearby.
Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Save 100% on your flight
per person
Feb 11 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a nightclub, and a rooftop terrace. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
per person
Feb 11 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hilton Chicago

Hilton Chicago

4 out of 5
Save 100% on your flight
per person
Feb 11 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
Stay at this 4-star historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
Save 100% on your flight
per person
Feb 11 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Kinzie Hotel

Kinzie Hotel

4 out of 5
Save 100% on your flight
per person
Feb 11 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy room service, a fitness center, and valet parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Save 100% on your flight
per person
Feb 11 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
Book a stay at this spa 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.
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
per person
Feb 11 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
Stay at this 4-star 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 Chicago Riverwalk and Michigan Avenue are located nearby.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
per person
Feb 11 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
Stay at this 5-star 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.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Save 100% on your flight
per person
Feb 11 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
Book a stay at this spa 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 Millennium Park and Chicago Riverwalk are located nearby.
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
Save 100% on your flight
per person
Feb 11 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.

3-4 Night Vacations in Old World Wisconsin

Price found within the past 48 hours. Click for updated prices.
Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
per person
Feb 7 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
per person
Feb 7 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Feb 14 - Feb 17
found 6 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
per person
Feb 7 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)

5-7 Night Vacations in Old World Wisconsin

Price found within the past 48 hours. Click for updated prices.
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Feb 11 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Feb 11 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
per person
Feb 11 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Feb 11 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)

Old World Wisconsin Last Minute Hotel Deals

Holiday Inn Express & Suites Elkhorn - Lake Geneva Area, an IHG Hotel
Holiday Inn Express & Suites Elkhorn - Lake Geneva Area, an IHG Hotel
2.5 out of 5
200 W O CONNOR DRIVE, Elkhorn, WI
Book a stay at this business-friendly hotel in Elkhorn. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Holiday Inn Express & Suites Elkhorn - Lake Geneva Area, an IHG Hotel
AmericInn by Wyndham Elkhorn Near Lake Geneva
AmericInn by Wyndham Elkhorn Near Lake Geneva
2.5 out of 5
210 East Commerce Court, Elkhorn, WI
Book a stay at this business-friendly motel in Elkhorn. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
AmericInn by Wyndham Elkhorn Near Lake Geneva
Timber Ridge Lodge and Waterpark
Timber Ridge Lodge and Waterpark
3.5 out of 5
7020 Grand Geneva Way, Lake Geneva, WI
Stay at this 3.5-star spa aparthotel in Lake Geneva. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the helpful staff and the ...
Timber Ridge Lodge and Waterpark
The Ingleside Hotel
The Ingleside Hotel
4 out of 5
2810 Golf Road, Pewaukee, WI
Stay at this 4-star business-friendly hotel in Pewaukee. Enjoy free WiFi, free parking, and water park access (surcharge). Our guests praise the helpful staff ...
The Ingleside Hotel
Grand Geneva Resort & Spa
Grand Geneva Resort & Spa
4 out of 5
7036 Grand Geneva Wy, Lake Geneva, WI
Stay at this 4-star spa resort in Lake Geneva. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
Grand Geneva Resort & Spa
Lake Lawn Resort
Lake Lawn Resort
3.5 out of 5
2400 E Geneva St, Delavan, WI
Stay at this 3.5-star beach resort in Delavan. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the pool and the bar in our reviews. ...
Lake Lawn Resort
Harbor Shores on Lake Geneva
Harbor Shores on Lake Geneva
3.5 out of 5
300 Wrigley Dr, Lake Geneva, WI
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 ...
Harbor Shores on Lake Geneva
Best Western Waukesha Grand
Best Western Waukesha Grand
2.5 out of 5
2840 N Grandview Boulevard, Pewaukee, WI
Book a stay at this business-friendly hotel in Pewaukee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Best Western Waukesha Grand
See all 1,690 properties in Old World Wisconsin
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.