Glenwood Vacations from $352

Book a Hotel + Flight or Car together to unlock savings

Your Glenwood Vacation

Lock in a Glenwood vacation package and get ready to experience this amazing city the easy way. Think about staying in the neighborhood of South Deering, which is good for golfing and nature. Fill up your itinerary with tours of Coyote Run Golf Course, River Oaks Center and Ravisloe Country Club, some of the things you really should see during a trip to Glenwood. Stop daydreaming and start doing. Explore the multitude of options on Expedia today and finally put your Glenwood vacation plans into motion!

The Latest Glenwood vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $735, price is now $352 per person
$352
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,602 reviews)
Very pleased with our stay. From the beginning to the end, the customer service was amazing. Room very clean and modern as well as the bathroom. You can definitely walk around and there are quite a few of dining options. Breakfast was amazing. Great quality for a free buffet. Will definitely return.

Reviewed on Oct 25, 2025

Art Villa

Art Villa

5 out of 5
West Town
Save 100% on your flight
Price was $964, price is now $456 per person
$456
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
10/10 Exceptional! (2 reviews)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was $1,020, price is now $483 per person
$483
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,110 reviews)
Ideal area if it’s your first time visiting Chicago. Hotel staff was very friendly.

Reviewed on Oct 16, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was $805, price is now $411 per person
$411
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (303 reviews)
Food price was high but everything was fine

Reviewed on Oct 4, 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $736, price is now $375 per person
$375
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,011 reviews)
Our guests that are not from Chicago there should be some sort of a quick tips handout that gives an overview of the events that are taking place over the next week popular restaurants things that are within walking distance of the hotel

Reviewed on Oct 20, 2025

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Glenwood Hotel Deals

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 Nov 2 to Nov 3
$146 total
Nov 2 - Nov 3
Total with taxes and fees
8.2/10 Very Good! (1,085 reviews)
Food overpriced. Breakfast and dinner.
$30 for a breakfast plate from the buffet. I’m counting my tip, is ridiculous.

Reviewed on Oct 22, 2025

Hilton Chicago/Oak Lawn
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
$52 nightly
The price is $58 total per night from Nov 17 to Nov 18
$58 total
Nov 17 - Nov 18
Total with taxes and fees
7/10 Good! (1,280 reviews)
Yes shopping near me.

Reviewed on Oct 25, 2025

Motel 6 Bridgeview, IL
Hampton Inn by Hilton Chicago-Midway Airport

Hampton Inn by Hilton Chicago-Midway Airport

2.5 out of 5
6540 S Cicero Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
$145 nightly
The price is $170 total per night from Nov 16 to Nov 17
$170 total
Nov 16 - Nov 17
Total with taxes and fees
8.4/10 Very Good! (1,282 reviews)
Airport shuttle was great

Reviewed on Oct 21, 2025

Hampton Inn by Hilton Chicago-Midway Airport
See all 880 properties in Glenwood
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 Glenwood Vacation Packages

Glenwood Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Midway Intl. Airport (MDW)
Population
9,000
Top Sights
Odyssey Fun World, Midwest Carvers Museum and William W. Powers State Recreation Area

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Frequently asked questions

How much does a Glenwood vacation package cost?
You can pick up a vacation package to this top destination from $352 on Expedia. But how much your vacation to Glenwood costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Glenwood?
December, January and February are the best times to look for cheap Glenwood vacation packages. Choosing to travel in quieter months means you can typically find better prices on accommodations and flights.
How many days is enough for Glenwood?
With a well-organized schedule, you can easily tick off the top Glenwood sights in a handful of days. But if you prefer to discover hidden spots or go on day tours, consider booking your Glenwood vacation for longer.
How to find the best Glenwood package deals?
Use Expedia's filters to help you find some of the best Glenwood package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or browse for Glenwood package deals in the low season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Glenwood vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll usually score a better deal than booking each component individually. And you'll still enjoy the flexibility to create a tailored Glenwood vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Glenwood?
If you've got your Glenwood vacation dates finalized, book early to snap up some awesome deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spontaneous adventures? Our last-minute deals are great for quick escapes.
Does Expedia offer Book Now, Pay Later Glenwood vacation packages?
If you're anything like us, you love traveling the world but are not a fan of the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the cost of your Glenwood break over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.