Homewood Vacations from $277

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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.
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $443, price is now $277 per person
$277
per person
Apr 9 - Apr 12
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (2,059 reviews)
Besides the ambience and location of this gorgeous hotel... we enjoyed winding down the evening with a drink and Bertha's brownie in the lobby/lounge.

Reviewed on Jan 18, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $638, price is now $337 per person
$337
per person
Apr 9 - Apr 12
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Everything was top tier, from the room being spotless, to the professionalism of the staff, to the breakfast buffet. I will be returning to the Chicago location and also trying the resort in Mexico soon!

Reviewed on Jan 20, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,572, price is now $892 per person
$892
per person
Mar 22 - Mar 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Exceptional service, great location, beautiful hotel

Reviewed on Jan 20, 2026

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,160, price is now $726 per person
$726
per person
Mar 23 - Mar 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
Yes didn’t know you get free breakfast

Reviewed on Jan 4, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $929, price is now $587 per person
$587
per person
Mar 23 - Mar 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Property was clean, welcoming, pet friendly

Reviewed on Jan 18, 2026

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Discover the most popular places to visit in Homewood

Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

4.5/5(332 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
Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

4.5/5(2,128 reviews)

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

Wrigley Field
Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(4,870 reviews)

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

Navy Pier

What to do in Homewood

Chicago Bulls Basketball Game at United Center

Chicago Bulls Basketball Game at United Center

$61
per adult
80% of travellers recommend
Chicago Bulls Basketball Game at United Center
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Chicago Blackhawks Ice Hockey Game at United Center

Chicago Blackhawks Ice Hockey Game at United Center

$67
per adult
Chicago Blackhawks Ice Hockey Game at United Center
See all activities in Homewood

Homewood Hotel Deals

The Champagne Lodge & Luxury Suites

The Champagne Lodge & Luxury Suites

3.5 out of 5
16 W 621 S. Frontage Rd Willowbrook IL
$119 nightly
The price is $124 total per night from Jan 21 to Jan 22
$124 total
Jan 21 - Jan 22
Total with taxes and fees
8.4/10 Very Good! (1,380 reviews)
Only rhinf

Reviewed on Jan 14, 2026

The Champagne Lodge & Luxury Suites
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
$53 nightly
The price is $59 total per night from Jan 27 to Jan 28
$59 total
Jan 27 - Jan 28
Total with taxes and fees
6.4/10 (1,023 reviews)
It was excellent just need a little more updating and freshness to the rooms and out side interior

Reviewed on Jan 18, 2026

Red Roof Inn PLUS+ Chicago - Willowbrook
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
$42 nightly
The price is $48 total per night from Jan 27 to Jan 28
$48 total
Jan 27 - Jan 28
Total with taxes and fees
7/10 Good! (1,360 reviews)
It was okay, seemed pretty secure.

Reviewed on Jan 17, 2026

Motel 6 Bridgeview, IL
See all 989 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.

Find the Best Homewood Vacation Packages

Homewood Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Midway Intl. Airport (MDW)
Population
19,400
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
Midwest Carvers Museum, Bronzeville Childrens Museum and William W. Powers State Recreation Area

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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 $277 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.