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.
Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)
The hotel staff were very pleasant, the room was clean, and the hotel was located in a convenient area.

Reviewed on Jul. 17, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
The room is spacious and the bedding is comfortable. The washroom is sparkling clean. The breakfast buffet is an excellent addition to our stay. We all love it.

Reviewed on Jul. 18, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
The property was very clean and well-maintained, offering an amazing view that made our stay truly memorable. Highly recommend for anyone looking for a relaxing and scenic getaway

Reviewed on Jul. 18, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Superb customer service, clean hotel!

Reviewed on Jun. 13, 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,785 reviews)
The servers and bartenders at the property were amazing! Gentleman who stored our luggage was polite and extremely attentive!

Reviewed on Jul. 16, 2025

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Homewood Hotel Deals

Holiday Inn Chicago SW-Countryside ConfCtr by IHG

Holiday Inn Chicago SW-Countryside ConfCtr by IHG

3.5 out of 5
6201 Joliet Rd, Countryside, IL
Fully refundable
The price is CA $158 per night from Aug 10 to Aug 11
CA $158
CA $177 total
Aug 10 - Aug 11
includes taxes & fees
7.8/10 Good! (1,037 reviews)
"Bien"

Reviewed on Jul. 16, 2025

Holiday Inn Chicago SW-Countryside ConfCtr by IHG
The Champagne Lodge & Luxury Suites

The Champagne Lodge & Luxury Suites

3.5 out of 5
16 W 621 S. Frontage Rd, Willowbrook, IL
The price is CA $117 per night from Jul 22 to Jul 23
CA $117
CA $159 total
Jul 22 - Jul 23
includes taxes & fees
8.4/10 Very Good! (1,161 reviews)
"I love it here!!!"

Reviewed on Jul. 15, 2025

The Champagne Lodge & Luxury Suites
Motel 6 Bridgeview, IL

Motel 6 Bridgeview, IL

2 out of 5
9625 S 76th Ave, Bridgeview, IL
Fully refundableReserve now, pay when you stay
The price is CA $87 per night from Jul 23 to Jul 24
CA $87
CA $97 total
Jul 23 - Jul 24
includes taxes & fees
6.8/10 (1,173 reviews)
Great
"Clean and comfortable, friendly staff."

Reviewed on Jul. 16, 2025

Motel 6 Bridgeview, IL
See all 922 properties in Homewood
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Discover the most popular places to visit in Homewood

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

4.5/5(158 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Navy Pier

Navy Pier

4.5/5(459 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
Magnificent Mile - River North which includes signage, a city and night scenes

Michigan Avenue

4.5/5(19 reviews)

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue

What to do in Homewood

River tour boat in Chicago

Architecture River Tour

CA $67
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $62
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

CA $62
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Homewood

Frequently asked questions

How much does a Homewood vacation package cost?
Offering excellent value package deals from CA $706 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?

  1. Choose your dates: The things you want to do in Homewood and your preferred season can help you decide when to get away.
  2. 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.
  3. 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.
  4. 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.