Exclusive Woodstock Square Vacation Deals
Woodstock Square vacation package deals
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,219, price is now CA $755 per person
CA $755
per person
Mar 11 - Mar 18
found 4 hours ago
Roundtrip flight included
Detroit (DTW) 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.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,906, price is now CA $1,059 per person
CA $1,059
per person
Mar 11 - Mar 18
found 4 hours ago
Roundtrip flight included
Detroit (DTW) 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.
Level Chicago – Old Town
Downtown Chicago
Price was CA $2,040, price is now CA $1,163 per person
CA $1,163
per person
Mar 11 - Mar 18
found 4 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
Book a stay at this 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.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $3,020, price is now CA $1,766 per person
CA $1,766
per person
Mar 11 - Mar 18
found 4 hours ago
Roundtrip flight included
Detroit (DTW) 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.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,556, price is now CA $926 per person
CA $926
per person
Mar 11 - Mar 18
found 4 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
Book a stay at this 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.
The Emily Hotel
Downtown Chicago
Price was CA $2,084, price is now CA $1,292 per person
CA $1,292
per person
Mar 11 - Mar 18
found 4 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
Book a stay at this business-friendly 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 United Center and Chicago Riverwalk are located nearby.
Frequently asked questions
Top Woodstock Square hotel deals
AmericInn by Wyndham Woodstock IL
990 Lake Avenue Woodstock IL
Free cancellation
Reserve now, pay when you stay
The price is CA $123 per night
CA $123
CA $137 total
Jan 6 - Jan 7, 2026
includes taxes & fees
Book a stay at this ski hotel in Woodstock. Enjoy free breakfast, free parking, and a casino. Our guests praise the clean rooms in our reviews. Popular attractions McHenry County Fairgrounds and Woodstock Opera House are located nearby.
Pool
Breakfast included
Hampton Inn McHenry
1555 South Route 31 McHenry IL
Free cancellation
Reserve now, pay when you stay
The price is CA $167 per night
CA $167
CA $185 total
Jan 1 - Jan 2, 2026
includes taxes & fees
Stay at this hotel in McHenry. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions McHenry Shores Beach Park and Moraine Hills State Park are located nearby.
Pool
Breakfast included
Don't see what you're looking for?
See all available properties in Woodstock Square
View all propertiesLowest 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.