Vacations Close To Old World Wisconsin

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Old World Wisconsin Flight + Hotel packages

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 $802, price is now $628 per person
$628
per person
Dec 1 - Dec 5
found 1 day ago
Roundtrip flight included
Little Rock (LIT) to Chicago (ORD)

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,530, price is now $998 per person
$998
per person
Dec 1 - Dec 5
found 1 day ago
Roundtrip flight included
Little Rock (LIT) to Chicago (ORD)
Great staff they accommodating us.

Reviewed on Oct 30, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was $1,115, price is now $800 per person
$800
per person
Dec 1 - Dec 5
found 1 day ago
Roundtrip flight included
Little Rock (LIT) to Chicago (ORD)
Staff was great and the room was clean!

Reviewed on Oct 29, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was $1,082, price is now $799 per person
$799
per person
Dec 1 - Dec 5
found 1 day ago
Roundtrip flight included
Little Rock (LIT) to Chicago (ORD)

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 out of 5
Downtown Chicago
Price was $1,097, price is now $857 per person
$857
per person
Dec 1 - Dec 5
found 1 day ago
Roundtrip flight included
Little Rock (LIT) to Chicago (ORD)

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was $1,314, price is now $1,027 per person
$1,027
per person
Dec 1 - Dec 5
found 1 day ago
Roundtrip flight included
Little Rock (LIT) to Chicago (ORD)

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Downtown Chicago
Price was $1,202, price is now $946 per person
$946
per person
Dec 1 - Dec 5
found 20 hours ago
Roundtrip flight included
Little Rock (LIT) to Chicago (ORD)

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was $1,087, price is now $856 per person
$856
per person
Dec 1 - Dec 5
found 1 day ago
Roundtrip flight included
Little Rock (LIT) to Chicago (ORD)

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Best Lodging Options Near Old World Wisconsin

Fairview Inn & Suites Whitewater

Fairview Inn & Suites Whitewater

2 out of 5
917 E Milwaukee St Whitewater WI
18.7 km from Old World Wisconsin
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. ...
Hampton Inn Elkhorn Lake Geneva Area

Hampton Inn Elkhorn Lake Geneva Area

2.5 out of 5
40 W Hidden Trail Elkhorn WI
19.42 km from Old World Wisconsin
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. ...
Staybridge Suites Milwaukee West-Oconomowoc by IHG

Staybridge Suites Milwaukee West-Oconomowoc by IHG

3 out of 5
1141 Blue Ribbon Drive Oconomowoc WI
22.27 km from Old World Wisconsin
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 ...
Grand Geneva Resort & Spa

Grand Geneva Resort & Spa

4 out of 5
7036 Grand Geneva Wy Lake Geneva WI
29.03 km from Old World Wisconsin
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 ...
The Ingleside Hotel

The Ingleside Hotel

4 out of 5
2810 Golf Road Pewaukee WI
26.76 km from Old World Wisconsin
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 ...
Lake Lawn Resort

Lake Lawn Resort

3.5 out of 5
2400 E Geneva St Delavan WI
27.86 km from Old World Wisconsin
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 ...
Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark

3.5 out of 5
7020 Grand Geneva Way Lake Geneva WI
30.05 km from Old World Wisconsin
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 ...
Best Western Waukesha Grand

Best Western Waukesha Grand

2.5 out of 5
2840 N Grandview Boulevard Pewaukee WI
27.46 km from Old World Wisconsin
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 ...
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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.