Name: Sleep Inn Midway Airport Bedford Park
Price range: CA $171
Rating: 8

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

Downtown Chicago

CA $921

per person

Aug 24 - Aug 27

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,327 reviews)

We stayed at this hotel for a small wedding venue. I booked the larger room and was glad I did. The hotel was close for walking to restaurants and some bars. The front desk was very friendly and helpful.

Reviewed on Jun 19, 2026

Level Chicago – Old Town

Downtown Chicago

CA $1,337

per person

Sep 2 - Sep 6

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (489 reviews)

We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.

Reviewed on Jun 11, 2026

Level Chicago - River North

Downtown Chicago

CA $1,262

per person

Aug 27 - Aug 31

found 17 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,019 reviews)

Really plan ahead when it comes to parking. You’ll get ticketed for just trying to put your things in your vehicle.

Reviewed on Jun 19, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

CA $1,667

per person

Jul 31 - Aug 3

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (2,535 reviews)

Great location and food court in area. Great for family fun

Reviewed on Jun 17, 2026

Pendry Chicago

Downtown Chicago

CA $1,138

per person

Aug 6 - Aug 9

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,127 reviews)

We were celebrating an anniversary. We had a greay stay. It was close to all the shopping and restaurants, staff were great and helpful. We will be back again!

Reviewed on Jun 18, 2026

Ready to book your vacation to Glenwood?

Choose your dates

Glenwood Hotel Deals

Holiday Inn Chicago – Midway Airport S by IHG

7353 S Cicero Avenue Chicago IL

Fully refundableReserve now, pay when you stay

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

Sleep Inn Midway Airport Bedford Park

6650 S Cicero Ave Chicago IL

Fully refundableReserve now, pay when you stay

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

Wind Creek Southland Casino and Hotel

17300 S Halsted St Hazel Crest IL

Fully refundableReserve now, pay when you stay

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

See all 921 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.