Homewood Vacations from ￥551,993
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Homewood Vacation Packages
Price found within the past 48 hours. Click for updated prices.
AC Hotels by Marriott Chicago Downtown
Downtown Chicago
￥554,988
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.8/10 Excellent! (1,009 reviews)
My family and I had a wonderful stay. The staff were awesome and the location is excellent. Rooms clean and comfortable. Chris the bell hop made our time there even more enjoyable. We are already planning our return trip!
Reviewed on Sep 12, 2026
Find the Best Homewood Vacation Packages
Homewood Hotel Deals
Holiday Inn Chicago – Midway Airport S by IHG
7353 S Cicero Avenue Chicago IL
Fully refundable
￥23,349
￥28,945 total
Sep 27 - Sep 28
includes taxes & fees
Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
￥25,983
￥30,502 total
Sep 20 - Sep 21
includes taxes & fees
7/10 Good! (1,002 reviews)
"Good"
Reviewed on Sep 12, 2026
Red Roof Inn PLUS+ Chicago - Willowbrook
7535 Kingery Highway Willowbrook IL
Fully refundableReserve now, pay when you stay
￥9,662
￥10,819 total
Sep 20 - Sep 21
includes taxes & 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.
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
￥7,453
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
￥3,886
per adult
90% of travellers recommend
Frequently asked questions
How much does a Homewood vacation package cost?
You can snap up a vacation package to this destination from ￥551,993 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?
January, June and September are the best times to look for cheap Homewood vacation packages. Traveling 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 vacation. 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 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.
How to plan a trip to Homewood?
- 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.
- 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.
- 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.
- Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a personalized Homewood vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
