Homewood Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €900 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 Flight + Hotel Deals in Homewood
Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection
Downtown Chicago
€974
per person
17 Sept - 21 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.4/10 Very good! (3,933 reviews)
The hotel was good and staff was helpful. My only complaint was the shower! There was little to no water pressure and at times we had to wait for any water at all.
Reviewed on 11 Aug 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
€1,216
per person
17 Sept - 21 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,631 reviews)
Overall the views were wonderful. The proximity was great. The room wasn’t clean. Bedding had stains on it. No one cleaned our room. No towels. Front desk was definitely not friendly. The elevator stopped working.
Reviewed on 11 Aug 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
€1,194
per person
17 Sept - 21 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,808 reviews)
Loved the hotel, loved the restaurants and room service
Staff was very kind. Perfect location
Reviewed on 11 Aug 2026
Top hotels in Homewood
Red Roof Inn PLUS+ Chicago - Willowbrook
7535 Kingery Highway Willowbrook IL
Fully refundableReserve now, pay when you stay
€61
17 Aug - 18 Aug
includes taxes & fees
Holiday Inn Chicago – Midway Airport S by IHG
7353 S Cicero Avenue Chicago IL
Fully refundable
€117
8 Sept - 9 Sept
includes taxes & fees
8.2/10 Very good! (1,036 reviews)
"Yes all was good"
Reviewed on 11 Aug 2026
Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
€172
31 Aug - 1 Sept
includes taxes & fees
7/10 Good! (1,021 reviews)
"First off, I have to say the two staff members at the front desk at check-in and -out were some of the friendliest, most welcoming, helpful hotel personnel I've ever encountered. Truly, ever. I wouldn't even be writing this review if not for them. Give them a raise. The room was fine. Very accessible. ..."
Reviewed on 10 Aug 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
Chicago: Navy Pier Centennial Wheel Ticket
€21
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 from €974 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.
