Vacations Close To Woodstock Square

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Woodstock Square 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
Downtown Chicago
Price was $665, price is now $530 per person
$530
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Little Rock (LIT) to Chicago (ORD)
Roman everything was clean everything was made that was all and it was very

Reviewed on Nov 4, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,033, price is now $731 per person
$731
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Little Rock (LIT) to Chicago (ORD)
1

Reviewed on Nov 4, 2026

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was $974, price is now $703 per person
$703
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Little Rock (LIT) to Chicago (ORD)

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was $833, price is now $650 per person
$650
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Little Rock (LIT) to Chicago (ORD)
Breakfast was good

Reviewed on Nov 4, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was $727, price is now $572 per person
$572
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Little Rock (LIT) to Chicago (ORD)

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was $822, price is now $676 per person
$676
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Little Rock (LIT) to Chicago (ORD)
This is my 3rd time staying at Eurostars and it was excellent as it always has been! Clean rooms, I appreciate the overnight valet, and it is in a great/safe location.

Reviewed on Nov 4, 2026

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Price was $861, price is now $715 per person
$715
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip non-stop 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 $786, price is now $653 per person
$653
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Little Rock (LIT) to Chicago (ORD)

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Best Lodging Options Near Woodstock Square

Abbey Resort and Avani Spa

Abbey Resort and Avani Spa

3.5 out of 5
269 Fontana Boulevard Fontana WI
28.04 km from Woodstock Square
Book a stay at this beach resort in Fontana. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the pool and the helpful staff in ...
The Geneva Inn

The Geneva Inn

3.5 out of 5
N2009 S Lake Shore Drive Lake Geneva WI
27.71 km from Woodstock Square
Stay at this hotel in Lake Geneva. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Geneva ...
Best Western Plus Elgin - Chicago

Best Western Plus Elgin - Chicago

3 out of 5
2175 Marriott Dr West Dundee IL
29.71 km from Woodstock Square
Book a stay at this business-friendly hotel in West Dundee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Harbor Shores on Lake Geneva

Harbor Shores on Lake Geneva

3.5 out of 5
300 Wrigley Dr Lake Geneva WI
30.49 km from Woodstock Square
Book a stay at this family-friendly hotel in Lake Geneva. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the pool and the helpful staff ...
The Cove Of Lake Geneva

The Cove Of Lake Geneva

3.5 out of 5
111 Center St Lake Geneva WI
30.54 km from Woodstock Square
Book a stay at this family-friendly hotel in Lake Geneva. Enjoy an outdoor pool, 2 hot tubs, and room service. Our guests praise the pool and the helpful staff ...
Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark

3.5 out of 5
7020 Grand Geneva Way Lake Geneva WI
32.01 km from Woodstock Square
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 ...
Extended Stay America Suites Chicago Elgin West Dundee

Extended Stay America Suites Chicago Elgin West Dundee

2.5 out of 5
2185 Marriott Dr West Dundee IL
29.72 km from Woodstock Square
Book a stay at this business-friendly hotel in West Dundee. Enjoy free breakfast, free parking, and a 24-hour fitness center. Popular attractions Santa's Village ...
Lodge Geneva National

Lodge Geneva National

4 out of 5
W4240 WI-50 Lake Geneva WI
30.32 km from Woodstock Square
Book a stay at this golf resort in Lake Geneva. Enjoy an outdoor pool, breakfast (surcharge), and a fitness center. Our guests praise the pool and the restaurant ...
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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.