Greenwood Vacations from US$329

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Your Greenwood Vacation

Prepare to experience Greenwood in your own style with a custom Greenwood vacation package! Discovering the best parts of this city is simpler with a base in a neighborhood such as Powers Lake, which is great for watersports, among plenty of other things. A trip to Greenwood is a great opportunity to sightsee. Be sure to visit renowned attractions like McHenry County Fairgrounds, Petersen Park Beach and McCullom Lake. Whatever your travel plans or budget, putting together the ultimate tailored Greenwood vacation is a breeze with Expedia.

The Latest Greenwood Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 25 - Aug 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
7.8/10 Good! (1,017 reviews)
The rooms could use a refrigerator

Reviewed on 1 Jun 2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
Jul 11 - Jul 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (208 reviews)
Loved all the neighborhood dogs & farmers market

Reviewed on 20 May 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 25 - Aug 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,212 reviews)
Bid room but not cleaned nor updated. Late check out is only at 1pm. No room upgrade offered. There was 1 day that room was not serviced until late evening. Good location

Reviewed on 2 Jun 2024

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
per person
Jul 11 - Jul 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,006 reviews)
Love the location close to all things necessities

Reviewed on 29 May 2024

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
per person
Jul 11 - Jul 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,142 reviews)
beautiful room and great staff

Reviewed on 3 Jun 2024

Greenwood Essential Information

Language
English
Currency
U.S dollars
Top Sights
Volo Auto Museum, McHenry Shores Beach Park and Petersen Park Beach

Greenwood Hotel Deals

The Ridge Hotel
The Ridge Hotel
4 out of 5
W4240 WI-50, Lake Geneva, WI
Fully refundableReserve now, pay when you stay
The price is $144 per night from Jun 9 to Jun 10
$144
$184 total
includes taxes & fees
9 Jun - 10 Jun
9/10 Wonderful! (1,018 reviews)
"We used to live in Lake Geneva so we already knew about what used to be called Interlaken. Some things are still outdated. The air conditioning units are dated go back many years and are extremely loud. They will wake you up"

Reviewed on 2 Jun 2024

The Ridge Hotel
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 $169 per night from Jun 17 to Jun 18
$169
$221 total
includes taxes & fees
17 Jun - 18 Jun
8.4/10 Very Good! (2,315 reviews)
"The little timber area was perfect for my 4yo. She really enjoyed it. They also have different activities for the kids during the day so it gives you some options if you don't want to be in the water park all day. Downtown Lake Geneva is also a short drive away if you want to get out of the resort. ..."

Reviewed on 1 Jun 2024

Timber Ridge Lodge and Waterpark
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
The price is $152 per night from Jun 4 to Jun 5
$152
$192 total
includes taxes & fees
4 Jun - 5 Jun
9/10 Wonderful! (1,199 reviews)
Great stay!
"Staff was great and room was clean."

Reviewed on 30 May 2024

Harbor Shores on Lake Geneva
See all 986 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Greenwood vacation package cost?
Less than you might think — from as low as US$329, actually! By bundling hotels, flights and car rentals into your own customized vacation package, your getaway to Greenwood is only clicks away.
How do I get a cheap travel package to Greenwood?
If you love getting an amazing deal, bundle your bookings into a Greenwood vacation package. Whether you’re searching for hotels, flights, rental cars or day tours, you can book them all in one place. You’ll have loads of choice at your fingertips as well. Expedia has over 550 air carriers and 1,000,000 properties globally to take your pick of. Fly with who you want, check in where you like and save precious money — now that’s the ideal getaway!
Where should I stay in Greenwood?
Cross Six Flags Great America off your must-see list and then stay moments from it. Experience the buzzing vibe around this well-known attraction and visit whenever you please!
How far in advance should I book my Greenwood vacation?
It all depends on the airline, but you can usually look up international airfares on Expedia up to 12 months in advance. While it’s advisable to book ahead of time, lucky customers will sometimes score a cheaper seat only weeks before departure dates.
What does an Expedia Greenwood travel package include?
It comes down to what you want. If you’re traveling alone, you might decide to combine hotels and flights. Bringing the entire family to Greenwood? A travel package that includes rental cars, flights and hotels might suit you better. Expedia gives you the flexibility to build your own travel package.
What should I know before booking a Greenwood travel package?
You can save a tidy sum by bundling your hotels, airfares and rental cars. Once you’ve created your package, you can add on tours and activities. Your next awesome adventure is only a few clicks away.
Can I choose my airline with a Greenwood Expedia vacation package?
Expedia has access to more than 550 partner airlines worldwide, so you certainly can. Simply select your preferred carrier and craft your ideal Greenwood trip.
If I'm not able to travel, can I cancel my Greenwood vacation package?
You sure can, and we’re here to help. You may be able to cancel or amend your Greenwood vacation package for free if you booked in the last 24 hours. But you may be charged a fee by your airline, hotel or car rental company if you booked more than 24 hours ago. If life gets in the way of your vacation, visit our Customer Service Portal for more information.

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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.