Homewood Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 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
Top hotels in Homewood
Sleep Inn Midway Airport Bedford Park
6650 S Cicero Ave Chicago IL
Fully refundableReserve now, pay when you stay
S$137
1 Nov - 2 Nov
includes taxes & fees
8/10 Very good! (2,162 reviews)
"Clean quiet friendly staff. We will stay here again"
Reviewed on 6 Oct, 2026
Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
S$203
1 Nov - 2 Nov
includes taxes & fees
7/10 Good! (1,005 reviews)
"Definitely a motel vibe, no elevator. Nice staff and clean rooms."
Reviewed on 5 Oct, 2026
Holiday Inn Chicago – Midway Airport S by IHG
7353 S Cicero Avenue Chicago IL
Fully refundable
S$221
26 Oct - 27 Oct
includes taxes & fees
8.2/10 Very good! (1,000 reviews)
"There was no bottled water available in the room or purchase up front. Limited resources. Won’t stay here again"
Reviewed on 7 Oct, 2026
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
Skydeck Chicago at Willis Tower
S$54
per adult
88% of travellers recommend
Frequently asked questions
How much does a Homewood holiday package cost?
You can snap up a holiday package to this destination 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?
- 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 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.
