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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.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Price was $505, price is now $351 per person
$351
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Price was $1,062, price is now $573 per person
$573
per person
Dec 18 - Dec 22
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy 3 restaurants, 2 bars/lounges, and breakfast (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

Hotel Riu Plaza Chicago

4 out of 5
Price was $1,060, price is now $665 per person
$665
per person
Dec 4 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,052, price is now $686 per person
$686
per person
Dec 23 - Dec 28
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $1,757, price is now $1,162 per person
$1,162
per person
Dec 23 - Dec 28
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Price was $749, price is now $510 per person
$510
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Nobu Hotel Chicago

Nobu Hotel Chicago

5 out of 5
Save 100% on your flight
Price was $1,436, price is now $1,003 per person
$1,003
per person
Dec 23 - Dec 28
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Chicago Riverwalk and United Center are located nearby.
The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago

5 out of 5
Save 100% on your flight
Price was $1,309, price is now $933 per person
$933
per person
Dec 23 - Dec 28
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Price was $502, price is now $360 per person
$360
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Save 100% on your flight
Price was $724, price is now $521 per person
$521
per person
Dec 24 - Dec 29
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Price was $644, price is now $464 per person
$464
per person
Dec 18 - Dec 22
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury 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 Michigan Avenue and Chicago Riverwalk are located nearby.
Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $633, price is now $457 per person
$457
per person
Dec 23 - Dec 28
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly 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 Michigan Avenue 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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was $413, price is now $294 per person
$294
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was $1,491, price is now $479 per person
$479
per person
Dec 20 - Dec 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was $793, price is now $561 per person
$561
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Kinzie Hotel

Kinzie Hotel

4 out of 5
Downtown Chicago
Price was $609, price is now $448 per person
$448
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

5-7 Night Vacations in Old World Wisconsin

Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $580, price is now $367 per person
$367
per person
Dec 23 - Dec 28
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was $3,147, price is now $734 per person
$734
per person
Dec 21 - Dec 26
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,039, price is now $603 per person
$603
per person
Dec 23 - Dec 28
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $635, price is now $401 per person
$401
per person
Dec 24 - Dec 29
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Old World Wisconsin Last Minute Hotel Deals

Fairview Inn & Suites Whitewater

Fairview Inn & Suites Whitewater

2 out of 5
917 E Milwaukee St Whitewater WI
Book a stay at this business-friendly hotel in Whitewater. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Fairview Inn & Suites Whitewater
Hampton Inn Elkhorn Lake Geneva Area

Hampton Inn Elkhorn Lake Geneva Area

2.5 out of 5
40 W Hidden Trail 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 in our reviews. ...
Hampton Inn Elkhorn Lake Geneva Area
Staybridge Suites Milwaukee West-Oconomowoc by IHG

Staybridge Suites Milwaukee West-Oconomowoc by IHG

3 out of 5
1141 Blue Ribbon Drive Oconomowoc WI
Stay at this hotel in Oconomowoc. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
Staybridge Suites Milwaukee West-Oconomowoc by IHG
Grand Geneva Resort & Spa

Grand Geneva Resort & Spa

4 out of 5
7036 Grand Geneva Wy Lake Geneva WI
Book a stay at this 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
The Ingleside Hotel

The Ingleside Hotel

4 out of 5
2810 Golf Road Pewaukee WI
Book a stay at this business-friendly hotel in Pewaukee. Enjoy free WiFi, free parking, and water park access (surcharge). Our guests praise the helpful staff ...
The Ingleside Hotel
Lake Lawn Resort

Lake Lawn Resort

3.5 out of 5
2400 E Geneva St Delavan WI
Book a stay at this beach resort in Delavan. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the pool and the helpful staff in ...
Lake Lawn Resort
Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark

3.5 out of 5
7020 Grand Geneva Way Lake Geneva WI
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 ...
Timber Ridge Lodge and Waterpark
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 1,724 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.