Glenwood Vacations from $238
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.
The Blackstone, Autograph Collection
Downtown Chicago
Save 100% on your flight
Price was $457, price is now $238 per person
$238
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,008 reviews)
Fabulous hotel we will be back
Reviewed on Oct 20, 2025
Pendry Chicago
Downtown Chicago
Price was $1,226, price is now $606 per person
$606
per person
Nov 25 - Dec 2
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
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $996, price is now $535 per person
$535
per person
Nov 25 - Dec 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,188 reviews)
Food from restaurant wasn’t fresh and was a little overpriced. Also check in is at 4:00 pm which is inconvenient if you reach early. Had to pay extra for early check in at 12:00 noon.
Reviewed on Oct 20, 2025
Hampton Inn & Suites Chicago Medical District UIC
Near West Side
Save 100% on your flight
Price was $673, price is now $369 per person
$369
per person
Nov 25 - Dec 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (281 reviews)
From the time we came through the front door we were greeted with a smile can’t remember their names but very good customer service rooms were great housekeeping gave me what I needed everyone greeted us every time we enter the lobby area Mike an Ashley checked us out with smiles they took time and ask how was our stay very knowledgeable about the billing also breakfast was excellent everything and everyone was great Thank you Jacqueline Robinson
Reviewed on Oct 21, 2025
Glenwood Hotel Deals
Hilton Chicago/Oak Lawn
9333 S Cicero Ave, Oak Lawn, IL
Fully refundableReserve now, pay when you stay
$123 nightly
The price is $142 total per night from Oct 29 to Oct 30
$142 total
Oct 29 - Oct 30
Total with taxes and fees
8.2/10 Very Good! (1,081 reviews)
"Room was clean and quiet. Key card stopped working and was required to operate elevator. That was slightly inconvenient but overall an enjoyable stay."
Reviewed on Oct 18, 2025
Motel 6 Bridgeview, IL
9625 S 76th Ave, Bridgeview, IL
Fully refundableReserve now, pay when you stay
$52 nightly
The price is $58 total per night from Nov 18 to Nov 19
$58 total
Nov 18 - Nov 19
Total with taxes and fees
7/10 Good! (1,260 reviews)
"Staff was very friendly, check in was easy and quick and included the WiFi info. TV screen is broken and bedsheet quality is iffy but otherwise it’s fine for a night."
Reviewed on Oct 13, 2025
Hampton Inn by Hilton Chicago-Midway Airport
6540 S Cicero Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
$145 nightly
The price is $170 total per night from Nov 9 to Nov 10
$170 total
Nov 9 - Nov 10
Total with taxes and fees
8.4/10 Very Good! (1,289 reviews)
"Airport shuttle was easy to access. Breakfast as good."
Reviewed on Oct 20, 2025
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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.