Homewood Vacation Packages
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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.
Top Homewood Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
CA $1,702
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
They charge a facilities fee which is about 20 bucks a night for the amenities. I generally don't have a problem with that as it includes breakfast. BUT, I was annoyed that in the hotel gym (which isn't bad), the bikes had some problems. It's a slight nitpick, admittedly, but that's what it is. The hotel is very close to transit and the LOOP which is the main area of Chicago. Staff were amazing and helpful, the breakfast was very filling. The gym has weights that go up to 20KG, which is pretty nice and they do have those gymbro slogans on the walls which is kind of fun.
Reviewed on Aug 22, 2026
The Talbott, Autograph Collection
Downtown Chicago
CA $1,447
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (157 reviews)
Front desk manager agreed to change my date with on-line service from the next weekend to the current weekend, so I booked and checked in.
4 days later, the on-line booking co. Said the manager did not agree to release my reservation.
Unethical procedurers.
Reviewed on Aug 12, 2026
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
CA $1,265
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very good! (2,089 reviews)
The location could not be better--close to Michigan Avenue and the Red Line L--and the property is clean, quiet, and safe. The only thing that rankled were the elevators, for which one typically has to wait years for: ended up taking the stairs often, and I was staying on the 9th floor.
Reviewed on Aug 21, 2026
Ready to book your vacation to Homewood?
Homewood Hotel Deals
Red Roof Inn PLUS+ Chicago - Willowbrook
7535 Kingery Highway Willowbrook IL
Fully refundableReserve now, pay when you stay
CA $87
CA $97 total
Aug 30 - Aug 31
includes taxes & fees
Holiday Inn Chicago – Midway Airport S by IHG
7353 S Cicero Avenue Chicago IL
Fully refundable
CA $157
CA $198 total
Sep 8 - Sep 9
includes taxes & fees
William Tell Hotel MOD Collection by Sonesta
6201 Joliet Rd Countryside IL
Fully refundableReserve now, pay when you stay
CA $146
CA $163 total
Sep 10 - Sep 11
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)
Enjoy a round of golf in Homewood at Ravisloe Country Club. Discover the area's great live music and shops.
What to do in Homewood
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $63
per adult
94% of travellers recommend
Frequently asked questions
How much does a Homewood vacation package cost?
Offering excellent value package deals from CA $1,099 on Expedia, you'll be pleasantly surprised at how much a vacation to Homewood costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Homewood?
If you're looking to book a cheap Homewood vacation package, consider travelling in January, June and September. You'll generally find lower rates on hotels and airfares during these quieter months — perfect for a budget-friendly getaway.
How many days is enough for Homewood?
To fully enjoy your Homewood vacation, we suggest booking for 2 days. Split your time between visiting Lansing Square Shopping Centre, Midwest Carvers Museum and other major sights, as well as exploring neighbourhoods like East Hazel Crest and Country Club Hills. If you've got some spare time, add a day trip or tour to your Homewood vacation itinerary.
How to find the best Homewood package deals?
Use Expedia's handy filters to help you find some great Homewood package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or search for Homewood package deals in the off-peak season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to book your vacation package as early as possible.
Is it cheaper to book a Homewood vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking flights and accommodations separately. Better still, you can customize your Homewood trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Homewood?
If you have your Homewood travel dates confirmed, book as early as you can to score some incredible deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are great for travelling on a whim.
How to plan a trip to Homewood?
- Choose your dates: The things you want to do in Homewood and your preferred season can help you decide when to get away.
- Set a budget: Factor in costs like flights, food and transportation when calculating how much to put aside for your trip to Homewood. Then, pick a hotel that suits your budget, whether that's an economical stay or a deluxe getaway.
- Work out your trip length: Consider how much time you'd like to spend exploring Homewood. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace.
- Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a tailored Homewood vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
