Homewood Vacations from $520

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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.
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $827, price is now $520 per person
$520
per person
Aug 8 - Aug 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (394 reviews)
The room was very nice and smelled very nice.

Reviewed on May 8, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $833, price is now $534 per person
$534
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,127 reviews)
Staff very friendly, more than willing to help and/or assist in any way. Beautiful hotel, love LOVE the roof top bar and patio. BEST buffet breakfast I've had in a very long time. I will definitely be booking with this hotel chain again!

Reviewed on May 22, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $995, price is now $648 per person
$648
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (474 reviews)
Minimum effort. Pleasant stay. Very quiet. Enjoyed the 8th floor common area. Service at the front desk was really great. Convenient coffee shop / bakery in the lobby.

Reviewed on May 18, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $875, price is now $575 per person
$575
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (480 reviews)
The rooms were very clean!

Reviewed on May 4, 2026

JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $885, price is now $582 per person
$582
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)
Good location close to many attractions like sears tower, the bean, river boat tours... nuce rooms ... public parking 1/2 block from premises .. just an overal great property with excellent convenience for tourists type activities

Reviewed on May 3, 2026

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Discover the most popular places to visit in Homewood

Wrigley Field

Wrigley Field

4.5/5(2,149 reviews)

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

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

4.5/5(461 reviews)

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Navy Pier

Navy Pier

4.5/5(4,925 reviews)

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

Navy Pier

What to do in Homewood

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$27
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

$44
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Art Institute of Chicago

Art Institute of Chicago

$40
per adult
92% of travellers recommend
Art Institute of Chicago
See all activities in Homewood

Homewood Hotel Deals

Sleep Inn Midway Airport Bedford Park

Sleep Inn Midway Airport Bedford Park

2.5 out of 5
6650 S Cicero Ave Chicago IL
Fully refundable
$111 nightly
The price is $131 total per night from May 25 to May 26
$131 total
May 25 - May 26
Total with taxes and fees
8/10 Very Good! (1,875 reviews)
"It had a decent am breakfast downstairs. Water pressure was good in shower. Very close to Midway airport. Just didnt like the additional hold of $100 on my card. Probably because of alot of bad instances there."

Reviewed on May 21, 2026

Sleep Inn Midway Airport Bedford Park
Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

2.5 out of 5
7353 S Cicero Avenue Chicago IL
Fully refundable
$145 nightly
The price is $168 total per night from Jun 7 to Jun 8
$168 total
Jun 7 - Jun 8
Total with taxes and fees
8.2/10 Very Good! (1,001 reviews)
"Very beautiful right when we arrived, we were greeted bar was great. The drinks were great. Happy hour. You do have to pay for parking, which is a very cheap price. The rooms were very clean. Love the full size mirrors."

Reviewed on May 21, 2026

Holiday Inn Chicago – Midway Airport S by IHG
DoubleTree by Hilton Chicago - Alsip

DoubleTree by Hilton Chicago - Alsip

4 out of 5
5000 W 127th St Alsip IL
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $138 total per night from May 31 to Jun 1
$138 total
May 31 - Jun 1
Total with taxes and fees
8.4/10 Very Good! (1,056 reviews)
"It was safe and people were friendly"

Reviewed on May 19, 2026

DoubleTree by Hilton Chicago - Alsip
See all 1,012 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 $520 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.