Woodstock Holidays

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Top Flight + Hotel Deals in Woodstock

Price found within the past 48 hours. Click for updated prices.
The Wade

The Wade

4.5 out of 5
Downtown Chicago
Price was €1,174, price is now €919 per person
€919
per person
7 Apr - 13 Apr
found 1 day ago
Return direct flight included
Porto (OPO) to Chicago (ORD)
8.4/10 Very Good! (1,444 reviews)
Room was very clean would return again

Reviewed on 23 Feb 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was €1,471, price is now €992 per person
€992
per person
7 Apr - 13 Apr
found 1 day ago
Return direct flight included
Porto (OPO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Clean amenities, amazing food, and great service!

Reviewed on 27 Feb 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was €1,284, price is now €919 per person
€919
per person
7 Apr - 13 Apr
found 1 day ago
Return direct flight included
Porto (OPO) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Room smelled like food but overall very clean, very great service and staff both night and morning shift.

Reviewed on 16 Feb 2026

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was €1,264, price is now €960 per person
€960
per person
7 Apr - 13 Apr
found 1 day ago
Return direct flight included
Porto (OPO) to Chicago (ORD)
9.2/10 Wonderful! (1,862 reviews)
Everything was great, I really enjoyed my stay!

Reviewed on 25 Feb 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was €1,250, price is now €962 per person
€962
per person
7 Apr - 13 Apr
found 1 day ago
Return direct flight included
Porto (OPO) to Chicago (ORD)
8.6/10 Excellent! (2,008 reviews)
amazing stay 10/10 would recommend

Reviewed on 26 Feb 2026

Top hotels in Woodstock

AmericInn by Wyndham Woodstock IL

AmericInn by Wyndham Woodstock IL

2.5 out of 5
990 Lake Avenue Woodstock IL
Fully refundableReserve now, pay when you stay
The price is €85 per night from 26 Mar to 27 Mar
€85
26 Mar - 27 Mar
includes taxes & fees
8/10 Very Good! (1,001 reviews)
.

Reviewed on 24 Feb 2026

AmericInn by Wyndham Woodstock IL
Abbey Resort and Avani Spa

Abbey Resort and Avani Spa

3.5 out of 5
269 Fontana Boulevard Fontana WI
Fully refundableReserve now, pay when you stay
The price is €116 per night from 15 Mar to 16 Mar
€116
15 Mar - 16 Mar
includes taxes & fees
8.6/10 Excellent! (1,756 reviews)
The room was great and front desk staff were very accommodating. Great location in town. Will be coming back next year.

Reviewed on 27 Feb 2026

Abbey Resort and Avani Spa
Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark

3.5 out of 5
7020 Grand Geneva Way Lake Geneva WI
Fully refundableReserve now, pay when you stay
The price is €166 per night from 3 Mar to 4 Mar
€166
3 Mar - 4 Mar
includes taxes & fees
Timber Ridge Lodge and Waterpark
See all 1,161 properties in Woodstock
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.

Popular places to visit

Crystal Woods Golf Club

Enjoy a round of golf in Woodstock at Crystal Woods Golf Club. Amble around the area's lakeside or attend a sporting event.

Crystal Woods Golf Club

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.