Glenwood Vacations from $501

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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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $760, price is now $501 per person
$501
per person
Sep 5 - Sep 8
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,854 reviews)
Small quiet rooms, but the location makes up for it.

Reviewed on Jul 28, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,165, price is now $705 per person
$705
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,770 reviews)

The Chicago Hotel Collection - Wrigleyville

The Chicago Hotel Collection - Wrigleyville

3.5 out of 5
Lakeview
Save 100% on your flight
Price was $1,692, price is now $1,127 per person
$1,127
per person
Sep 28 - Oct 5
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
7/10 Good! (1,007 reviews)
Room and bed were very comfortable. Unfortunately, the location ended up being incredibly loud late into the early morning hours.

Reviewed on Jul 27, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $798, price is now $542 per person
$542
per person
Oct 4 - Oct 7
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (504 reviews)

Holiday Inn Chicago North-Evanston by IHG

Holiday Inn Chicago North-Evanston by IHG

3 out of 5
Downtown Evanston
Save 100% on your flight
Price was $919, price is now $632 per person
$632
per person
Oct 13 - Oct 19
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.6/10 Excellent! (2,028 reviews)
Very close to the Northwestern University

Reviewed on Jul 28, 2026

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Glenwood Hotel Deals

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 refundableReserve now, pay when you stay
$113 nightly
The price is $131 total per night from Aug 9 to Aug 10
$131 total
Aug 9 - Aug 10
Total with taxes and fees
Holiday Inn Chicago – Midway Airport S by IHG
Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

3 out of 5
4900 S Lake Shore Dr Chicago IL
$199 nightly
The price is $234 total per night from Aug 4 to Aug 5
$234 total
Aug 4 - Aug 5
Total with taxes and fees
Chicago Lake Shore Hotel
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
$110 nightly
The price is $129 total per night from Aug 18 to Aug 19
$129 total
Aug 18 - Aug 19
Total with taxes and fees
8/10 Very Good! (2,010 reviews)
"This place is outdated and not the safest location. I should've chosen a different location."

Reviewed on Jul 28, 2026

Sleep Inn Midway Airport Bedford Park
See all 911 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 $501 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.