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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.
Four Points by Sheraton Chicago Westchester/Oak Brook

Four Points by Sheraton Chicago Westchester/Oak Brook

3 out of 5
Save 100% on your flight
Price was $344, price is now $210 per person
$210
per person
Dec 3 - Dec 8
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Westchester. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Oak Brook Golf Course and Graue Mill and Museum are located nearby.
Hilton Orrington / Evanston

Hilton Orrington / Evanston

4 out of 5
Price was $671, price is now $384 per person
$384
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Evanston. 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 Clark Street Beach and Halim Time & Glass Museum are located nearby.
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Price was $486, price is now $313 per person
$313
per person
Dec 9 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star 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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Price was $1,322, price is now $651 per person
$651
per person
Nov 25 - Dec 2
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star 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.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $401, price is now $215 per person
$215
per person
Dec 18 - Dec 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star 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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $558, price is now $314 per person
$314
per person
Dec 18 - Dec 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Save 100% on your flight
Price was $481, price is now $281 per person
$281
per person
Dec 18 - Dec 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star 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.
DoubleTree by Hilton Chicago - North Shore Conference Center

DoubleTree by Hilton Chicago - North Shore Conference Center

4 out of 5
Save 100% on your flight
Price was $467, price is now $277 per person
$277
per person
Dec 3 - Dec 8
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Skokie. Enjoy free parking, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions North Shore Center for the Performing Arts and Skokie Theatre are located nearby.
The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago

5 out of 5
Save 100% on your flight
Price was $2,049, price is now $1,217 per person
$1,217
per person
Nov 25 - Dec 2
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 5-star 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.
The Wade

The Wade

4.5 out of 5
Save 100% on your flight
Price was $548, price is now $332 per person
$332
per person
Dec 3 - Dec 8
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Navy Pier are located nearby.
DoubleTree by Hilton Chicago - Alsip

DoubleTree by Hilton Chicago - Alsip

4 out of 5
Save 100% on your flight
Price was $567, price is now $346 per person
$346
per person
Nov 24 - Nov 29
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (MDW)
Stay at this 4-star business-friendly hotel in Alsip. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hollywood Park and Gaelic Park are located nearby.
Holiday Inn Express Chicago - Magnificent Mile by IHG

Holiday Inn Express Chicago - Magnificent Mile by IHG

2.5 out of 5
Save 100% on your flight
Price was $509, price is now $318 per person
$318
per person
Dec 3 - Dec 8
found 23 hours 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 a fitness center. Our guests praise the breakfast and the helpful staff 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.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $267, price is now $177 per person
$177
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $840, price is now $345 per person
$345
per person
Nov 24 - Nov 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $415, price is now $243 per person
$243
per person
Nov 24 - Nov 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $322, price is now $213 per person
$213
per person
Nov 24 - Nov 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.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was $785, price is now $382 per person
$382
per person
Dec 3 - Dec 8
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hilton Orrington / Evanston

Hilton Orrington / Evanston

4 out of 5
Downtown Evanston
Price was $671, price is now $384 per person
$384
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,041, price is now $459 per person
$459
per person
Dec 3 - Dec 8
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was $1,322, price is now $651 per person
$651
per person
Nov 25 - Dec 2
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Old World Wisconsin Last Minute Hotel Deals

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
Holiday Inn Express & Suites Elkhorn - Lake Geneva Area by IHG

Holiday Inn Express & Suites Elkhorn - Lake Geneva Area by IHG

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 by IHG
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
Baymont by Wyndham Waterford/Burlington WI

Baymont by Wyndham Waterford/Burlington WI

2.5 out of 5
750 Fox Lane, Waterford, WI
Book a stay at this business-friendly hotel in Waterford. Enjoy free breakfast, free WiFi, and free parking. Popular attraction Green Meadows Petting Farm is ...
Baymont by Wyndham Waterford/Burlington WI
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
Skyview Inn

Skyview Inn

2.5 out of 5
733 Milwaukee Ave, Burlington, WI
Stay at this motel in Burlington. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Echo Veterans Memorial Park and Logic Puzzle Museum ...
Skyview Inn
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
See all 1,689 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.