Vacations Close To Woodstock Square

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Woodstock Square Flight + Hotel packages

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THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Downtown Chicago
Price was $621, price is now $477 per person
$477
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
This place is absolutely disgusting. It’s great when you walk in, but the rooms are literally falling apart. The bar has extreme overpriced drinks. We had to mojitos and it was $46. Worse than Nashville- LOL. There was hair on the beds, the walls and light covers are peeling and there is hardly any space to walk in the rooms. This place is trash. I’m in Chicago a lot and I will never return to this “hotel” (motel?)

Reviewed on Sep 12, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,228, price is now $806 per person
$806
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Very accommodating

Reviewed on Sep 13, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $852, price is now $603 per person
$603
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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
Save 100% on your flight
Price was $933, price is now $682 per person
$682
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)

Renaissance Chicago Downtown Hotel

Renaissance Chicago Downtown Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $951, price is now $701 per person
$701
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)

River Hotel

River Hotel

4 out of 5
Downtown Chicago
Price was $732, price is now $553 per person
$553
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)

Stay One Chicago

Stay One Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,215, price is now $919 per person
$919
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)

The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,451, price is now $1,109 per person
$1,109
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Excellent staff.

Reviewed on Sep 8, 2026

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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 ...
Comfort Suites Elgin Northwest

Comfort Suites Elgin Northwest

2.5 out of 5
2480 Bushwood Drive Elgin IL
26.38 km from Woodstock Square
Book a stay at this business-friendly hotel in Elgin. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
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 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 ...
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 ...
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 ...
Fairfield Inn & Suites by Marriott Lake Geneva

Fairfield Inn & Suites by Marriott Lake Geneva

3 out of 5
1111 NORTH EDWARDS BOULEVARD Lake Geneva WI
29.26 km from Woodstock Square
Book a stay at this business-friendly hotel in Lake Geneva. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
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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.