Homewood Holidays

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Homewood Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
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 19 hours 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 19 hours 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 19 hours 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 19 hours 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 19 hours 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

Top hotels in Homewood

Red Roof Inn PLUS+ Chicago - Willowbrook

Red Roof Inn PLUS+ Chicago - Willowbrook

2.5 out of 5
7535 Kingery Highway, Willowbrook, IL
Fully refundableReserve now, pay when you stay
The price is S$85 per night from 1 Sept to 2 Sept
S$85
1 Sept - 2 Sept
includes taxes & fees
6.2/10 (1,005 reviews)
"Chilis Target"

Reviewed on 16 Aug, 2025

Red Roof Inn PLUS+ Chicago - Willowbrook
The Champagne Lodge & Luxury Suites

The Champagne Lodge & Luxury Suites

3.5 out of 5
16 W 621 S. Frontage Rd, Willowbrook, IL
The price is S$153 per night from 8 Sept to 9 Sept
S$153
8 Sept - 9 Sept
includes taxes & fees
8.4/10 Very Good! (1,206 reviews)
"It was a great stay, the room was nice the tub was amazing. Will be staying again!"

Reviewed on 22 Aug, 2025

The Champagne Lodge & Luxury Suites
Hilton Chicago/Oak Lawn

Hilton Chicago/Oak Lawn

3.5 out of 5
9333 S Cicero Ave, Oak Lawn, IL
Fully refundableReserve now, pay when you stay
The price is S$187 per night from 1 Sept to 2 Sept
S$187
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (1,013 reviews)
"Nice"

Reviewed on 22 Aug, 2025

Hilton Chicago/Oak Lawn
See all 966 properties in Homewood
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

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

Wrigley Field

4.5/5(40 reviews)

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

4.5/5(36 reviews)

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

4.5/5(147 reviews)

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

Millennium Park

What to do in Homewood

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 Homewood

Frequently asked questions

How much does a Homewood holiday package cost?
You can snap up a holiday package to this destination from S$1,733 on Expedia. But how much your holiday to Homewood costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Homewood?
January, June and September are the best times to look for cheap Homewood holiday packages. Travelling in less busy periods means you'll typically find lower prices on flights and hotels.
How many days is enough for Homewood?
Typically, a handful of days is enough to explore the main attractions during your Homewood holiday. However, if you'd like to have some time to unwind or take day tours, consider extending your trip.
How to find the best Homewood package deals?
Bagging a cheap Homewood package deal is easy with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget, add a few filters and browse what's available. You can tailor your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Homewood package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Homewood holiday as a package?
Expedia holiday packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component individually. And you'll still have the freedom to create a tailored Homewood holiday by choosing your preferred airline, accommodation type and car class.
When to book a holiday package to Homewood?
If you're planning a spur-of-the-moment Homewood getaway, browse our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can find incredible deals on your flights and hotels by booking well in advance.
How to plan a trip to Homewood?

  1. Choose when to get away: Check your calendar and get packing. Your preferred season and the available activities will also help you decide when to escape to Homewood.
  2. Budget wisely: Besides the cost of your stay, you should consider other expenses too. These include flights, transportation and food. Also, set aside a little extra for unexpected expenses that may arise during your trip to Homewood.
  3. Set the duration of your trip: Start by making a list of all the activities and sights you want to experience in Homewood. 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 hotels, car rental, flights and more into a personalised Homewood holiday package.

* 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.