Homewood Vacations from $486
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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.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
$873
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,960 reviews)
Great location in downtown Chicago. Building was very quaint and the staff was extremely friendly and accommodating!
Reviewed on Aug 30, 2026
The Peninsula Chicago
Downtown Chicago
$2,925
per person
Nov 3 - Nov 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.8/10 Exceptional! (1,006 reviews)
The service and the staff iare incredible, do professional!!
So many details!
My husband and I were so happy!!
Reviewed on Aug 25, 2026
Stay near popular Homewood attractions
Ravisloe Country Club
7.6/10 (4 reviews)
This Donald Ross-designed golf course challenges players with its rolling mounds and deep bunkers. Experience classic golfing on meticulously maintained greens, then enjoy a meal at the elegant clubhouse.
What to do in Homewood
Chicago: Willis Tower Skydeck and The Ledge Ticket
$47
per adult
88% of travellers recommend
Homewood Hotel Deals
Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
$169 nightly
$199 total
Aug 31 - Sep 1
Total with taxes and fees
Holiday Inn Chicago – Midway Airport S by IHG
7353 S Cicero Avenue Chicago IL
Fully refundable
$137 nightly
$159 total
Sep 7 - Sep 8
Total with taxes and fees
8.2/10 Very Good! (1,012 reviews)
"Our only complaints were the coffee bar was not open while we were there and the bistro was hard to tell they were open. The breakfast buffet was 30min late to start. We asked for shuttle service and it was not running on Saturday morning."
Reviewed on Aug 30, 2026
Sleep Inn Midway Airport Bedford Park
6650 S Cicero Ave Chicago IL
Fully refundable
$127 nightly
$149 total
Sep 27 - Sep 28
Total with taxes and fees
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 $486 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.
Explore a world of travel with Expedia
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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.
