Homewood Vacations from $236

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Your Homewood Vacation

Come and discover this interesting city for yourself with a Homewood vacation package. Think about basing yourself in the neighborhood of South Deering, which is good for golfing and nature, and your time here is bound to be unforgettable. A trip to Homewood is an excellent opportunity to do a bit of sightseeing. Be sure to look around popular attractions like Hollywood Casino Amphitheatre, Coyote Run Golf Course and River Oaks Center. Your Homewood vacation is a few clicks away. Browse airfares, hotels and more on Expedia for a getaway that's tailored to suit your travel style.

The Latest Homewood vacation packages

Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Wind Creek Southland Casino and Hotel
Hotel Riu Plaza Chicago
The Emily Hotel
Trump International Hotel & Tower Chicago
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What to do in Homewood

Homewood Hotel Deals

Holiday Inn Chicago SW-Countryside ConfCtr by IHG

Holiday Inn Chicago SW-Countryside ConfCtr by IHG

3.5 out of 5
6201 Joliet Rd Countryside IL
Fully refundable
$95 nightly
The price is $106 total per night from Dec 12 to Dec 13
$106 total
Dec 12 - Dec 13
Total with taxes and fees
7.8/10 Good! (1,291 reviews)
Very satisfying! Clean room actually the best hotel in Illinois I been to well return again

Reviewed on Dec 1, 2025

Holiday Inn Chicago SW-Countryside ConfCtr by IHG
The Champagne Lodge & Luxury Suites

The Champagne Lodge & Luxury Suites

3.5 out of 5
16 W 621 S. Frontage Rd Willowbrook IL
$120 nightly
The price is $126 total per night from Dec 8 to Dec 9
$126 total
Dec 8 - Dec 9
Total with taxes and fees
8.4/10 Very Good! (1,353 reviews)
Staff was very helpful. A little disappointed that they took out the steamroom but i still enjoyed the jetted tub.

Reviewed on Nov 30, 2025

The Champagne Lodge & Luxury Suites
Hyatt Place Chicago Midway Airport

Hyatt Place Chicago Midway Airport

3 out of 5
6550 S Cicero Ave Chicago IL
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $149 total per night from Dec 8 to Dec 9
$149 total
Dec 8 - Dec 9
Total with taxes and fees
9/10 Wonderful! (1,195 reviews)
Fast, easy check in. Very clean and reasonably priced hotel. The staff was very friendly and helpful. It’s also very close to Midway Airport.

Reviewed on Dec 1, 2025

Hyatt Place Chicago Midway Airport
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.

Find the Best Homewood Vacation Packages

Homewood Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Midway Intl. Airport (MDW)
Population
19,400
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
Midwest Carvers Museum, Bronzeville Childrens Museum and William W. Powers State Recreation Area

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Frequently asked questions

How much does a Homewood vacation package cost?
You can snap up a vacation package to this destination from $236 on Expedia. But how much your vacation 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?
You can generally find lower prices and better availability in March, June and December. Take a look at our cheap Homewood vacation packages and you could score some excellent off-season deals.
How many days is enough for Homewood?
With a well-organized travel plan, you can easily hit the top Homewood attractions in a few days. But if you want to venture off the beaten track or take day trips, consider booking your Homewood vacation for longer.
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 traveling on a weekday, when prices are generally lower.
Is it cheaper to book a Homewood vacation as a package?
Expedia vacation 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 vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation 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.
Does Expedia offer Book Now, Pay Later Homewood vacation packages?
If you're like us, you love exploring new places but are not a fan of the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the cost of your Homewood vacation across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure great vacation packages with payment plans as soon as you see them.

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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.