Name: Hilton Chicago/Oak Lawn
Price range: CA $149
Rating: 8.2

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!

Top Glenwood Vacation Deals

Price found within the past 48 hours. Click for updated prices.

La Banque Hotel

CA $727

per person

Apr 22 - Apr 25

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Chicago (ORD)

9.4/10 Exceptional! (447 reviews)

Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.

Reviewed on Jan 26, 2026

The Emily Hotel

Downtown Chicago

CA $1,160

per person

Apr 14 - Apr 19

found 5 hours ago

Roundtrip non-stop flight included

Calgary (YYC) to Chicago (ORD)

9.2/10 Wonderful! (1,264 reviews)

Amazing hotel. Always stay here when I make a trip to Chicago.

Reviewed on Feb 10, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

CA $790

per person

Apr 23 - Apr 26

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (2,790 reviews)

Room was clean, staff was so polite and kind and very helpful. We took our 3 year old daughter with us and they were kind to her and welcoming! (That means a lot - not all hotels are welcoming to small children.) they made sure to open the doors for us each time we came in with our stroller. We will absolutely be back to the Riu in Chicago! 10/10

Reviewed on Feb 9, 2026

Aloft Chicago Downtown River North

Downtown Chicago

CA $764

per person

Mar 31 - Apr 4

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,159 reviews)

Staff was great but next to fire station. Beware very noisy if staying city view

Reviewed on Feb 8, 2026

Hyatt Centric Chicago Magnificent Mile

Downtown Chicago

CA $1,085

per person

Apr 16 - Apr 21

found 8 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (1,034 reviews)

All good. bar staff was not that friendlly

Reviewed on Feb 3, 2026

Ready to book your vacation to Glenwood?

Choose your dates

Glenwood Hotel Deals

Motel 6 Bridgeview, IL

9625 S 76th Ave Bridgeview IL

Fully refundableReserve now, pay when you stay

CA $67

CA $76 total

Feb 15 - Feb 16

includes taxes & fees

7/10 Good! (1,378 reviews)

Nice

Reviewed on Jan 29, 2026

DoubleTree by Hilton Chicago - Alsip

5000 W 127th St Alsip IL

Fully refundableReserve now, pay when you stay

CA $132

CA $150 total

Feb 22 - Feb 23

includes taxes & fees

8.4/10 Very Good! (1,002 reviews)

everything

Reviewed on Feb 6, 2026

Hilton Chicago/Oak Lawn

9333 S Cicero Ave Oak Lawn IL

Fully refundableReserve now, pay when you stay

CA $149

CA $171 total

Feb 18 - Feb 19

includes taxes & fees

8.2/10 Very Good! (1,205 reviews)

Clean room

Reviewed on Feb 6, 2026

See all 950 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.