Glenwood Vacations from $365

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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.
La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $597, price is now $365 per person
$365
per person
Nov 12 - Nov 15
found 15 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
9.4/10 Exceptional! (434 reviews)
Very nice hotel. Would definitely stay there again!

Reviewed on Aug 26, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was $1,466, price is now $748 per person
$748
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,192 reviews)
I loved the location - it was very walkable and lots of restaurants/shops nearby. The room itself was average - beds were very low and the furniture was kind of odd - mostly plywood built ins. But the one room served it's purpose and was clean. The issue was, I had reserved TWO rooms, but when I arrived I was informed they only had one room for me. Apparently they didn't accept the second room reservation... Neither the Emily nor Expedia notified me that one of my "PREPAID" rooms was not reserved. There were NO rooms available in the Hotel for Saturday, nor in the entire city of Chicago on Labor Day weekend, so we were left scrambling to find a place to accomodate the six of us (i.e friends couches, etc.). Not sure which company is ultimately to blame, but needless to say, ALWAYS double check your reservation with this place before you travel.

Reviewed on Sep 3, 2025

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $913, price is now $537 per person
$537
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,002 reviews)
A beautiful step back in time with modern amenities. Amazing staff and easy access to anything you want to do in the city.

Reviewed on Aug 21, 2025

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Save 100% on your flight
Price was $1,012, price is now $614 per person
$614
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,103 reviews)
easy going to downtown, airport… Thanks for the convenient experience

Reviewed on Sep 1, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $782, price is now $477 per person
$477
per person
Oct 31 - Nov 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,342 reviews)
Have stay at multiple Riu hotel in my many travel. Always a great value. Their breakfast is exceptional and the service is always above average.

Reviewed on Sep 4, 2025

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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 $365 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.