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Woodstock Square Vacation Packages

Woodstock Square Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
Save 100% on your flight
per person
Jul 18 - Jul 22
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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 helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Art Institute of Chicago are located nearby.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Save 100% on your flight
per person
Jul 18 - Jul 22
found 19 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the restaurant and the bar in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
per person
Jul 18 - Jul 22
found 19 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Kinzie Hotel

Kinzie Hotel

4 out of 5
Save 100% on your flight
per person
Jul 18 - Jul 22
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy room service, a fitness center, and valet parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Save 100% on your flight
per person
Jul 18 - Jul 22
found 19 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

4 out of 5
Save 100% on your flight
per person
Jul 18 - Jul 22
found 19 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
per person
Jul 18 - Jul 22
found 19 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Save 100% on your flight
per person
Jul 18 - Jul 22
found 19 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Willis Tower and Chicago Riverwalk are located nearby.
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
Save 100% on your flight
per person
Jul 18 - Jul 22
found 19 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Stay at this 3-star hotel in Chicago. Enjoy free WiFi, room service, and a 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
Save 100% on your flight
per person
Jul 18 - Jul 22
found 19 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Stay at this 4-star spa aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Save 100% on your flight
per person
Jul 18 - Jul 22
found 19 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Grant Park and Soldier Field are located nearby.
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Save 100% on your flight
per person
Jul 18 - Jul 22
found 19 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, 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.

3-4 Night Vacations in Woodstock Square

Price found within the past 48 hours. Click for updated prices.
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 18 - Jul 22
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Kinzie Hotel

Kinzie Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 18 - Jul 22
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 1 - Aug 4
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 18 - Jul 22
found 19 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)

5-7 Night Vacations in Woodstock Square

Price found within the past 48 hours. Click for updated prices.
Ambassador Chicago, part of JdV by Hyatt

Ambassador Chicago, part of JdV by Hyatt

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 31 - Aug 5
found 1 day ago
Roundtrip non-stop flight included
Sacramento (SMF) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 31 - Aug 5
found 1 day ago
Roundtrip non-stop flight included
Sacramento (SMF) 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
per person
Jul 31 - Aug 5
found 1 day ago
Roundtrip non-stop flight included
Sacramento (SMF) to Chicago (ORD)
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 31 - Aug 5
found 1 day ago
Roundtrip non-stop flight included
Sacramento (SMF) to Chicago (ORD)

Woodstock Square Last Minute Hotel Deals

Country Inn & Suites by Radisson, Elgin, IL
Country Inn & Suites by Radisson, Elgin, IL
2.5 out of 5
2270 Point Blvd, Elgin, IL
Book a stay at this business-friendly hotel in Elgin. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular ...
Country Inn & Suites by Radisson, Elgin, IL
Abbey Resort and Avani Spa
Abbey Resort and Avani Spa
3.5 out of 5
269 Fontana Boulevard, Fontana, WI
Stay at this 3.5-star beach resort in Fontana. Enjoy free parking, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
Abbey Resort and Avani Spa
The Ridge Hotel
The Ridge Hotel
4 out of 5
W4240 WI-50, Lake Geneva, WI
Stay at this 4-star golf resort in Lake Geneva. Enjoy an outdoor pool, breakfast (surcharge), and a fitness center. Our guests praise the pool and the restaurant ...
The Ridge Hotel
Harbor Shores on Lake Geneva
Harbor Shores on Lake Geneva
3.5 out of 5
300 Wrigley Dr, Lake Geneva, WI
Book a stay at this family-friendly hotel in Lake Geneva. Enjoy free WiFi, free parking, and room service. Our guests praise the pool and the helpful staff in ...
Harbor Shores on Lake Geneva
The Geneva Inn
The Geneva Inn
3.5 out of 5
N2009 S Lake Shore Drive, Lake Geneva, WI
Stay at this 3.5-star hotel in Lake Geneva. Enjoy free WiFi, free parking, and room service. Our guests praise the restaurant and the helpful staff in our reviews. ...
The Geneva Inn
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, a full-service spa, and a golf course. Our guests praise the helpful staff and the clean ...
Timber Ridge Lodge and Waterpark
Sonesta Select Chicago Elgin West Dundee
Sonesta Select Chicago Elgin West Dundee
3 out of 5
2175 Marriott Dr, West Dundee, IL
Stay at this 3-star business-friendly hotel in West Dundee. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
Sonesta Select Chicago Elgin West Dundee
The Cove Of Lake Geneva
The Cove Of Lake Geneva
3.5 out of 5
111 Center St, Lake Geneva, WI
Stay at this 3.5-star family-friendly hotel in Lake Geneva. Enjoy an outdoor pool, room service, and a fitness center. Our guests praise the pool and the helpful ...
The Cove Of Lake Geneva
See all 1,704 properties in Woodstock Square
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.

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Spirit Airlines
Tue, Aug 27 - Wed, Aug 28
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$119 Roundtrip, found 6 days ago
$119
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Tue, Aug 27 from Los Angeles Intl. to O'Hare Intl., returning Wed, Aug 28, priced at $119 found 6 days ago
Frontier Airlines
Wed, Sep 11 - Sat, Sep 14
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$150 Roundtrip, found 2 hours ago
$150
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Wed, Sep 11 from Los Angeles Intl. to O'Hare Intl., returning Sat, Sep 14, priced at $150 found 2 hours ago
United
Sat, Aug 31 - Wed, Sep 4
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$151 Roundtrip, found 3 days ago
$151
Roundtrip
found 3 days ago
Select United flight, departing Sat, Aug 31 from Los Angeles Intl. to O'Hare Intl., returning Wed, Sep 4, priced at $151 found 3 days ago
United
Wed, Jun 26 - Thu, Jul 25
HKG
Hong Kong Intl.
ORD
O'Hare Intl.
$1,146 Roundtrip, found 3 days ago
$1,146
Roundtrip
found 3 days ago
Select United flight, departing Wed, Jun 26 from Hong Kong Intl. to O'Hare Intl., returning Thu, Jul 25, priced at $1,146 found 3 days ago

Book the perfect getaway to Woodstock Square

With Hotwire, booking your next trip to Woodstock is a breeze. When it comes to planning a show-stopping vacay, you’re the reigning champion of doing it on a dime. You love to plan exciting destination adventures while saving money on a budget.

Hotwire is here to help you plan a smooth sailing trip to Woodstock Square while saving some major cash. Doubling up on vacation expenses like hotel and car rentals and fun-filled excursions can save you money—especially when you book one of Hotwire’s vacation packages.

If your trip to is spur-of-the-moment and you’re leaving soon, Hotwire can save you up to 60% off your rentals with Hotwire Hot Rate deals. Book with Hotwire to grab a stellar Woodstock Square flight and hotel package for as low as $446.

Living it up in Woodstock means getting there in style and staying in a hotel that matches your mood. Book one of Hotwire’s Woodstock Square, Woodstock vacation packages to enjoy the best of both worlds. Flight and hotel packages typically include roundtrip non-stop flights and multi-day hotel stays. Packages are priced per person and are perfect for flying solo or traveling with a group of friends or family. Conveniently choose from Hotwire’s inventory of hotels in Woodstock Square for some of the best accommodations and flight deals.

FAQs about cheap Woodstock Square packages:

How to get cheap vacation deals to Woodstock Square?

Save up to 60% off vacation deals with Hotwire Hot Rates. Just plug in your general preferences and let Hotwire choose matching hotels for as low as $75.

How much are Woodstock Square packages?

Vacation packages to Woodstock Square vary in price. They are priced per person and include discounted hotel and flight costs. With Hotwire, you can score a vacation package for as low as $446.

How to find cheap car rentals near Woodstock Square?

Hotwire partners with some of the most reliable car rental companies in Woodstock to bring you the best car rental deals in Woodstock Square for as low as . Select a rental from Hotwire’s extensive inventory of cars for every travel style. If you plan on bringing friends or family along, opt for a spacious SUV. If you’re visiting on business but still plan to make time for off-the-clock adventures, Hotwire offers sleek luxury and convertible rentals.

Is it safe to travel to Woodstock Square now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to Woodstock Square right now?” When it’s time to book your vacation, check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.

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