Homewood Vacations from $308

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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.

The Latest Homewood vacation packages

Price found within the past 48 hours. Click for updated prices.
Hampton Inn Chicago-Carol Stream

Hampton Inn Chicago-Carol Stream

2.5 out of 5
Save 100% on your flight
Price was $465, price is now $308 per person
$308
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (1,010 reviews)
Nicely renovated rooms! A pleasure to stay!

Reviewed on Aug 24, 2025

Hyatt Regency Deerfield

Hyatt Regency Deerfield

4 out of 5
Save 100% on your flight
Price was $724, price is now $420 per person
$420
per person
Nov 10 - Nov 16
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (1,002 reviews)
⭐️⭐️⭐️⭐️⭐️ Hotel Review: Hyatt Regency Deerfield I stayed at the Hyatt Regency Deerfield from Friday to Sunday, and it was truly a wonderful experience! The rooms were cozy, spotless, and very comfortable, making it easy to relax after a busy weekend. The staff was exceptional—warm, welcoming, and attentive in every interaction. The dining facility was excellent, with both the food and service exceeding expectations. After attending the John Legend concert, returning to the hotel felt like coming to a home away from home. Kudos to the entire team at Hyatt Regency Deerfield for making the stay memorable. I’ll definitely return and highly recommend this hotel!

Reviewed on Aug 25, 2025

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Save 100% on your flight
Price was $1,058, price is now $642 per person
$642
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,099 reviews)
Proximity to all gates at airport

Reviewed on Aug 23, 2025

Harrah's Joliet Casino & Hotel

Harrah's Joliet Casino & Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,030, price is now $681 per person
$681
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (CHI)
8.4/10 Very Good! (998 reviews)
Very nice and quiet. Staff very friendly

Reviewed on Aug 9, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,144, price is now $757 per person
$757
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
It is a beautiful, well maintained property. The staff is the true gem of the property. They elevate the visitors experience to a new level of excellence.

Reviewed on Aug 25, 2025

Don't see what you're looking for?
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Discover the most popular places to visit in Homewood

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

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

Wrigley Field
Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

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
Navy Pier featuring a sunset and rides

Navy Pier

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

Navy Pier

What to do in Homewood

River tour boat in Chicago

Architecture River Tour

$41
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

$41
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

$45
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Homewood

Homewood Hotel Deals

Red Roof Inn PLUS+ Chicago - Willowbrook

Red Roof Inn PLUS+ Chicago - Willowbrook

2.5 out of 5
7535 Kingery Highway, Willowbrook, IL
Fully refundableReserve now, pay when you stay
$59 nightly
The price is $66 total per night from Sep 1 to Sep 2
$66 total
Sep 1 - Sep 2
Total with taxes and fees
6.2/10 (1,007 reviews)
"Good coffee"

Reviewed on Aug 24, 2025

Red Roof Inn PLUS+ Chicago - Willowbrook
The Champagne Lodge & Luxury Suites

The Champagne Lodge & Luxury Suites

3.5 out of 5
16 W 621 S. Frontage Rd, Willowbrook, IL
$124 nightly
The price is $130 total per night from Sep 8 to Sep 9
$130 total
Sep 8 - Sep 9
Total with taxes and fees
8.4/10 Very Good! (1,213 reviews)
"Our stay was wonderful. The property was very clean. Staff were polite and welcoming. We really enjoyed soaking in the hot tub & winding down from our busy lives. I would highly recommend a getaway!"

Reviewed on Aug 24, 2025

The Champagne Lodge & Luxury Suites
Hilton Chicago/Oak Lawn

Hilton Chicago/Oak Lawn

3.5 out of 5
9333 S Cicero Ave, Oak Lawn, IL
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $146 total per night from Sep 1 to Sep 2
$146 total
Sep 1 - Sep 2
Total with taxes and fees
Hilton Chicago/Oak Lawn
See all 966 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.

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Frequently asked questions

How much does a Homewood vacation package cost?
You can snap up a vacation package to this destination from $308 on Expedia. But how much your vacation 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?
You can generally find lower prices and better availability in March, June and December. Take a look at our cheap Homewood vacation packages and you could score some excellent off-season deals.
How many days is enough for Homewood?
With a well-organized travel plan, you can easily hit the top Homewood attractions in a few days. But if you want to venture off the beaten track or take day trips, consider booking your Homewood vacation for longer.
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 traveling on a weekday, when prices are generally lower.
Is it cheaper to book a Homewood vacation as a package?
Expedia vacation 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 vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation 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.
Does Expedia offer Book Now, Pay Later Homewood vacation packages?
If you're like us, you love exploring new places but are not a fan of the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the cost of your Homewood vacation across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.