Greenwood Holidays

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Top Flight + Hotel Deals in Greenwood

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

The Emily Hotel

4 out of 5
Downtown Chicago
Price was €1,228, price is now €755 per person
€755
per person
6 Nov - 10 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,159 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend. Also the coffee bags ? PERFECTION. Just had to add that

Reviewed on 22 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was €1,927, price is now €1,159 per person
€1,159
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.

Reviewed on 19 Aug 2025

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Price was €1,428, price is now €866 per person
€866
per person
4 Oct - 10 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (2,028 reviews)
Close to walk most places. Lots of restaurants in the surrounding area. Staff very nice. Rooms clean and spacious.

Reviewed on 22 Aug 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was €1,968, price is now €1,235 per person
€1,235
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on 10 Aug 2025

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
Price was €1,712, price is now €1,116 per person
€1,116
per person
4 Oct - 10 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
A beautiful step back in time with modern amenities. Amazing staff and easy access to anything you want to do in the city.

Reviewed on 21 Aug 2025

Top hotels in Greenwood

Harbor Shores on Lake Geneva

Harbor Shores on Lake Geneva

3.5 out of 5
300 Wrigley Dr, Lake Geneva, WI
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (1,222 reviews)
"Accessibility"

Reviewed on 20 Aug 2025

Get rates
Harbor Shores on Lake Geneva
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 €122 per night from 23 Sept to 24 Sept
€122
23 Sept - 24 Sept
includes taxes & fees
8.4/10 Very Good! (1,469 reviews)
"Perfect place for a quick romantic getaway, to spend time with family and friends , quick girlfriend weekend, kids friendly"

Reviewed on 22 Aug 2025

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 €172 per night from 23 Sept to 24 Sept
€172
23 Sept - 24 Sept
includes taxes & fees
8.6/10 Excellent! (2,960 reviews)
"We love the waterpark for our 5 and 3 year olds! The room was great with the separate bedroom and the full sized fridge!"

Reviewed on 20 Aug 2025

Timber Ridge Lodge and Waterpark
See all 1,038 properties in Greenwood
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.

Frequently asked questions

How much does a Greenwood holiday package cost?
You'll find cheap prices from €755 on Expedia for your Greenwood escape. However, factors like your choice of hotel, the season and length of stay will influence how much your holiday to Greenwood costs.
What are the cheapest months to go to Greenwood?
January, February and March are great times to search for cheap Greenwood holiday packages. Choosing to travel in quieter periods means you can typically find lower prices on flights and accommodation.
How many days is enough for Greenwood?
The ideal length of your Greenwood holiday depends on what you'd like to see and do. Typically, a handful of days to a week will give you plenty of time to go to all the top sights and explore some hidden treasures along the way.
How to find the best Greenwood package deals?
Begin your search for a Greenwood package deal by entering your travel dates and destination under our "Packages" tab. Then add some filters, like "Popular locations" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Greenwood package deal straight away, just switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Greenwood escape underway.
Is it cheaper to book a Greenwood holiday as a package?
Expedia holiday packages are designed to help you keep more cash in your pocket. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll typically snag a better deal than booking each component individually. And you'll still have the freedom to create a personalised Greenwood holiday by choosing your preferred accommodation type, airline and car class.
When to book a holiday package to Greenwood?
If you're considering a spur-of-the-moment Greenwood getaway, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can find amazing deals on your hotels and flights by booking ahead.
How to plan a trip to Greenwood?

  1. Choose your dates: What you want to do in Greenwood and your favourite season can help you decide when to get away.
  2. Set your budget: Consider costs such as food, flights and transportation when calculating how much to save for your trip to Greenwood. Then, select a property that suits your budget, whether that's a low-cost option or a swankier retreat.
  3. Determine how many days away: Start by making a list of all the activities and sights you'd like to experience in Greenwood. Then, estimate how long you'll need at each, including any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a customised Greenwood holiday package.

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