Glenwood Vacations from $216

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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.
Holiday Inn Aurora North - Naperville by IHG
La Banque Hotel
Fairmont Chicago at Millennium Park
Hotel Riu Plaza Chicago
Warwick Allerton - Chicago
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Glenwood Hotel Deals

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
$55 nightly
The price is $62 total per night from Feb 15 to Feb 16
$62 total
Feb 15 - Feb 16
Total with taxes and fees
7/10 Good! (1,390 reviews)
Very clean

Reviewed on Feb 10, 2026

Motel 6 Bridgeview, IL
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
$98 nightly
The price is $110 total per night from Feb 22 to Feb 23
$110 total
Feb 22 - Feb 23
Total with taxes and fees
8.4/10 Very Good! (1,001 reviews)
Staff was very courteous and very helpful. Hotel is older and could use an update. As always, the cookies were delicious!!

Reviewed on Feb 2, 2026

DoubleTree by Hilton Chicago - Alsip
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
$110 nightly
The price is $126 total per night from Feb 18 to Feb 19
$126 total
Feb 18 - Feb 19
Total with taxes and fees
8.2/10 Very Good! (1,213 reviews)
Nice room

Reviewed on Feb 9, 2026

Hilton Chicago/Oak Lawn
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 $216 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.