Glenwood Holidays from £1,296
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Your Glenwood Holiday
Lock in a Glenwood holiday package and get ready to experience this amazing city the easy way. Think about staying in the neighbourhood of South Deering, which is good for golfing and nature. Fill up your itinerary with tours of Coyote Run Golf Course, River Oaks Centre 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 holiday plans into motion!
Top Glenwood Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was £1,712, price is now £1,296 per person
£1,296
per person
30 Jul - 3 Aug
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,727 reviews)
We stayed in this hotel in our daughter's wedding weekend. It was wonderful, the river and city view from our 18th story room was spectacular. I recommend it to.all ages.
Reviewed on 7 Jun 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was £1,876, price is now £1,398 per person
£1,398
per person
30 Jul - 3 Aug
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,519 reviews)
This is an amazing place. Everything you can think of all under 1 roof. My hotel view was amazing. I am looking forward to coming annually.
Reviewed on 8 Jun 2026
Level Chicago – Old Town
Downtown Chicago
Price was £1,964, price is now £1,495 per person
£1,495
per person
20 Aug - 25 Aug
found 6 hours ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (481 reviews)
Very clean and loved the location and amenities with the store on the first floor was fantastic
Reviewed on 3 Jun 2026
Omni Chicago Hotel
Downtown Chicago
Price was £1,701, price is now £1,330 per person
£1,330
per person
30 Jul - 3 Aug
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,791 reviews)
beautiful room
city view
excellent location
quiet and comfortable
Reviewed on 9 Jun 2026
Glenwood Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Midway Intl. Airport (MDW) |
Population | 9,000 |
Max Temp Winter | -1.11ºC |
Max Temp Summer | 27ºC |
Top Sights | Odyssey Fun World, Midwest Carvers Museum and William W. Powers State Recreation Area |
Top hotels in Glenwood
Holiday Inn Chicago – Midway Airport S by IHG
7353 S Cicero Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is £101 per night from 28 Jun to 29 Jun
£101
28 Jun - 29 Jun
includes taxes & fees
8.2/10 Very Good! (1,021 reviews)
"Property had horrible beds, rooms small, bathroom light horrible. Bathroom small. Just not comfortable or inviting. Would not stay again. Smokers blocking door so have to walk through cigarette smoke just to get to room."
Reviewed on 8 Jun 2026
Sleep Inn Midway Airport Bedford Park
6650 S Cicero Ave Chicago IL
Fully refundable
The price is £100 per night from 30 Jun to 1 Jul
£100
30 Jun - 1 Jul
includes taxes & fees
8/10 Very Good! (1,913 reviews)
"The hotel was okey, honestly I’m trying to sleep and the other guess was so loud. I didn’t sleep at all."
Reviewed on 8 Jun 2026
DoubleTree by Hilton Chicago - Alsip
5000 W 127th St Alsip IL
Fully refundableReserve now, pay when you stay
The price is £115 per night from 6 Jul to 7 Jul
£115
6 Jul - 7 Jul
includes taxes & fees
8.4/10 Very Good! (1,080 reviews)
"A very nice hotel. Easy to find and well-maintained. Big, beautiful indoor pool. We enjoyed before leaving in the morning for the Chicago Blues Festival."
Reviewed on 8 Jun 2026
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. Flight-inclusive packages are ATOL protected.
