Homewood Vacation Packages
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- Plan, book, travel with confidence
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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.
Trump International Hotel & Tower Chicago
Downtown Chicago
CA $2,124
per person
Nov 19 - Nov 24
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
We had the most memorable time… we flew out from California to see my 5 yr old granddaughter for the weekend . Thank you Sharon and staff for making my weekend with her a day she will always remember. I have highly recommended this hotel to all my law enforcement partners. Thank you and we will be back.
Reviewed on Oct 7, 2026
Ready to book your vacation to Homewood?
Homewood Hotel Deals
Sleep Inn Midway Airport Bedford Park
6650 S Cicero Ave Chicago IL
Fully refundableReserve now, pay when you stay
CA $129
CA $152 total
Nov 1 - Nov 2
includes taxes & fees
8/10 Very good! (2,154 reviews)
"Clean quiet friendly staff. We will stay here again"
Reviewed on Oct 6, 2026
Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
CA $192
CA $225 total
Nov 1 - Nov 2
includes taxes & fees
7/10 Good! (1,005 reviews)
"Definitely a motel vibe, no elevator. Nice staff and clean rooms."
Reviewed on Oct 5, 2026
Holiday Inn Chicago – Midway Airport S by IHG
7353 S Cicero Avenue Chicago IL
Fully refundable
CA $198
CA $246 total
Oct 25 - Oct 26
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 Oct 7, 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)
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
Skydeck Chicago at Willis Tower
CA $59
per adult
88% 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 $1,067 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.
