Winchester-Hood Garden Homes Holidays

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Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
O'Hare
Price was S$2,105, price is now S$1,733 per person
S$1,733
per person
12 Oct - 19 Oct
found 1 day ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
8.8/10 Excellent! (2,288 reviews)
Chip painting in shower/tub

Reviewed on 22 Aug, 2025

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Price was S$2,898, price is now S$2,234 per person
S$2,234
per person
12 Oct - 19 Oct
found 1 day ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
8.2/10 Very Good! (2,099 reviews)
Proximity to all gates at airport

Reviewed on 23 Aug, 2025

Sonesta Chicago O'Hare Airport Rosemont

Sonesta Chicago O'Hare Airport Rosemont

3 out of 5
O'Hare
Price was S$2,301, price is now S$1,843 per person
S$1,843
per person
12 Oct - 19 Oct
found 1 day ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
8.6/10 Excellent! (1,537 reviews)
Not worth the price.

Reviewed on 21 Aug, 2025

Staybridge Suites Chicago O'Hare - Rosemont by IHG

Staybridge Suites Chicago O'Hare - Rosemont by IHG

3 out of 5
O'Hare
Price was S$2,224, price is now S$1,802 per person
S$1,802
per person
12 Oct - 19 Oct
found 1 day ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
8.8/10 Excellent! (1,012 reviews)
It was a very nice place. I don’t agree with the parking fees and then the added on three dollar Eco fee when nursing to be parking right beside it that was the cities and didn’t seem like very of secure parking. It wasn’t fenced in or anything just I don’t understand the fee for the parking Other night. It was a stay

Reviewed on 24 Aug, 2025

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

3.5 out of 5
O'Hare
Price was S$2,181, price is now S$1,844 per person
S$1,844
per person
12 Oct - 19 Oct
found 1 day ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
8.6/10 Excellent! (2,393 reviews)
Pool was extremely chlorinated

Reviewed on 24 Aug, 2025

Where to stay in Winchester-Hood Garden Homes

Find the best Winchester-Hood Garden Homes areas and neighborhoods for the activities you enjoy most. Learn more about Winchester-Hood Garden Homes
Downtown Chicago which includes a city

Downtown Chicago

5 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

Top hotels in Winchester-Hood Garden Homes

The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$227 per night from 1 Sept to 2 Sept
S$227
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (1,218 reviews)
"Friendly"

Reviewed on 24 Aug, 2025

The Wade
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$283 per night from 14 Sept to 15 Sept
S$283
14 Sept - 15 Sept
includes taxes & fees
7.8/10 Good! (8,994 reviews)
"Transportation by bus or subway is within a 5 minute walk, very easy. Hotel is across from a beautiful park. Lobby is nice but the hallways look very rough. It’s an old hotel with basic upgrades. Rooms were clean but shows it age. Beds were comfy. We checked our luggage upon arrival because our room ..."

Reviewed on 23 Aug, 2025

Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$229 per night from 3 Sept to 4 Sept
S$229
3 Sept - 4 Sept
includes taxes & fees
8.4/10 Very Good! (4,774 reviews)
"The staff were very accommodating and nice. The rooms were spacious and comfortable."

Reviewed on 24 Aug, 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,605 properties in Winchester-Hood Garden Homes
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 Winchester-Hood Garden Homes holiday package cost?
Handcraft your Winchester-Hood Garden Homes holiday package from just S$1,733. Pick from any combination of rental cars, flights and hotels to create the escape of your dreams. Be sure to add on a few experiences or tours!
How do I get a cheap travel package to Winchester-Hood Garden Homes?
Our Winchester-Hood Garden Homes holiday packages promise plenty of savings for the savvy explorer. For the best deal, simply bundle your flights, hotels and extras (including activities) into a neat and tidy package. But impressive bargains are only the start of your next awesome adventure. When you book with Expedia, and you'll have over 550 air carriers and 1,000,000 hotels all over the world to choose from. Whatever your style, there's a holiday package that's perfect for you.
Where should I stay in Winchester-Hood Garden Homes?
Choose a hotel within walking distance of Lincoln Park. This fantastic sight is in the heart of the action and on the must-do lists of most travellers.
How far in advance should I book my Winchester-Hood Garden Homes holiday?
Reserving your spot early with Expedia means one less thing to worry about. Many air carriers display prices up to 12 months prior to departure dates. Typically, this is the cheapest time to book. If circumstances have left you booking late, last-minute deals to Winchester-Hood Garden Homes are still known to appear just a few weeks before departure.
What does an Expedia Winchester-Hood Garden Homes travel package include?
Flights, hotels and a cool set of wheels for all your road trip adventures. Simply pick and choose your favourite bundle and get access to incredible deals. Once you've made your booking, add on some sightseeing tours and watch your savings stack up. When it comes to organising your Winchester-Hood Garden Homes break, you're the boss!
What should I know before booking a Winchester-Hood Garden Homes travel package?
A travel package can be easier on the bank balance than separately booking everything you need for your getaway. For example, bundle your hotels, flights and rental cars and save big. Whatever your holiday goals are, you're bound to find a package that's right for you.
Can I choose my airline with a Winchester-Hood Garden Homes Expedia holiday package?
Yes, and with over 550 airlines to select from across the globe, you've got lots of choice. Browse the available options and find out which airline best fits your needs and budget.
If I'm not able to travel, can I cancel my Winchester-Hood Garden Homes holiday package?
If your holiday plans in Winchester-Hood Garden Homes have been upended, it's comforting to know that it's possible to cancel or amend your booking. If you made your booking in the last 24 hours, you may be able to get a refund. If your booking is older than that, your airline, hotel or car rental company may charge a cancellation fee. To find out more, check our Customer Service Portal.

Popular places to visit

Wrigley Field which includes a sporting event, a city and central business district

Wrigley Field

Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.

Wrigley Field
McCormick Place

McCormick Place

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Millennium Park which includes modern architecture, a city and autumn leaves

Millennium Park

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park

Things to do

River tour boat in Chicago

Architecture River Tour

S$53
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

S$52
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

S$58
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Chicago

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.