Glenwood Vacation Packages

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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!

Top Glenwood Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Emily Hotel
Level Chicago – Old Town
Level Chicago - River North
Sable at Navy Pier Chicago, Curio Collection by Hilton
Pendry Chicago

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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
The price is CA $172 per night from Jul 5 to Jul 6
CA $172
CA $216 total
Jul 5 - Jul 6
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
"Poorly managed staff and poorly trained. Took more than two hours to check in due to an employee mistake. Unable to talk to manager. Not help at desk during checkout. Pay for parking was muncher higher for this area and well above other close hotels of higher caliber."

Reviewed on Jun 17, 2026

Holiday Inn Chicago – Midway Airport S by IHG
Sleep Inn Midway Airport Bedford Park

Sleep Inn Midway Airport Bedford Park

2.5 out of 5
6650 S Cicero Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $171 per night from Jun 28 to Jun 29
CA $171
CA $200 total
Jun 28 - Jun 29
includes taxes & fees
8/10 Very Good! (1,920 reviews)
"Love the free shuttle They have the best coffee in town"

Reviewed on Jun 19, 2026

Sleep Inn Midway Airport Bedford Park
Wind Creek Southland Casino and Hotel

Wind Creek Southland Casino and Hotel

4 out of 5
17300 S Halsted St Hazel Crest IL
Fully refundableReserve now, pay when you stay
The price is CA $207 per night from Jun 22 to Jun 23
CA $207
CA $232 total
Jun 22 - Jun 23
includes taxes & fees
9.2/10 Wonderful! (445 reviews)
"Great location off the highway. Short travel distance into downtown Chicago. Great stay!"

Reviewed on Jun 19, 2026

Wind Creek Southland Casino and Hotel
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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.