Glenwood Holidays from £966

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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.
SureStay Plus Hotel by Best Western Chicago Lombard

SureStay Plus Hotel by Best Western Chicago Lombard

2.5 out of 5
Highland Hills
per person
4 Nov - 7 Nov
found 7 hours ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (2,161 reviews)
Room needed updating.

Reviewed on 9 Aug 2025

Chez Hotel Arlington Heights

Chez Hotel Arlington Heights

4 out of 5
per person
4 Nov - 7 Nov
found 7 hours ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (396 reviews)
Very nice hotel. New, very clean, staff did offer new roof bar and restaurant that recently opened. No ironing board and iron but that wasn’t a big deal.

Reviewed on 7 Aug 2025

Bluegreen Vacations Hotel Blake, Ascend Resort Collection

Bluegreen Vacations Hotel Blake, Ascend Resort Collection

4 out of 5
Downtown Chicago
per person
4 Nov - 7 Nov
found 7 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (1,005 reviews)
Great hotel To stay at :)

Reviewed on 9 Aug 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
4 Nov - 7 Nov
found 7 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,270 reviews)
This was my first time staying. The staff was very friendly and helpful. Our room was very nice and perfectly located downtown. Also, the breakfast buffet was amazing and a nice surprise.

Reviewed on 9 Aug 2025

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
Downtown Chicago
per person
4 Nov - 7 Nov
found 7 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,927 reviews)
Nice, traditional property with friendly valets

Reviewed on 10 Aug 2025

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

Motel 6 Bridgeview, IL

Motel 6 Bridgeview, IL

2 out of 5
9625 S 76th Ave, Bridgeview, IL
Fully refundableReserve now, pay when you stay
The price is £45 per night from 27 Aug to 28 Aug
£45
27 Aug - 28 Aug
includes taxes & fees
6.8/10 (1,197 reviews)
Saved
"Staff was super helpful and made us feel welcomed after checking out of another motel in the area."

Reviewed on 4 Aug 2025

Motel 6 Bridgeview, IL
Hilton Chicago/Oak Lawn

Hilton Chicago/Oak Lawn

3.5 out of 5
9333 S Cicero Ave, Oak Lawn, IL
Fully refundableReserve now, pay when you stay
The price is £109 per night from 17 Aug to 18 Aug
£109
17 Aug - 18 Aug
includes taxes & fees
8/10 Very Good! (1,002 reviews)
"Great place, great area too."

Reviewed on 6 Aug 2025

Hilton Chicago/Oak Lawn
Ameristar Casino Hotel East Chicago

Ameristar Casino Hotel East Chicago

4 out of 5
777 Ameristar Blvd., East Chicago, IN
Fully refundableReserve now, pay when you stay
The price is £100 per night from 1 Sept to 2 Sept
£100
1 Sept - 2 Sept
includes taxes & fees
8.4/10 Very Good! (1,004 reviews)
"It was very nice , smaller casino great service at the bar !! Very friendly people"

Reviewed on 7 Aug 2025

Ameristar Casino Hotel East Chicago
See all 887 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Glenwood travel package cost?
We make it easy to travel somewhere new, with Glenwood travel packages starting from as low as £966. You'll have the flexibility to combine your favourite hotels, airlines and car rental. For the ultimate getaway, why not add some experiences and tours to your travel itinerary?
If I'm not able to travel, can I cancel my Glenwood travel package?
We get it — life sometimes gets in the way of your plans. If you've locked in a Glenwood travel package and have to change or cancel it, we're here to help. We recommend checking out our Customer Service Portal first for information. But generally, if you've booked your package in the last 24 hours, you may be able to change your itinerary free of charge. If it's been longer than 24 hours, your hotel, airline or car rental company may impose a charge.
How do I get a cheap travel package to Glenwood?
Booking a Glenwood travel package with Expedia is a simple way to save. We have access to more than 550 partner airlines and 1,000,000 hotel options globally. With such a huge range to pick from, you'll have no trouble putting together your next dream trip.
Does Expedia offer Book Now, Pay Later Glenwood holidays?
Your bank balance shouldn't stop you from escaping on holiday, so Expedia has worked out a solution to help. Thanks to our partnership with online lender Klarna, it's easier than ever to book a dream getaway without drying up your savings. Klarna offers flexible payment options during the checkout process that take the stress out of budgeting for your escape. Check out these flexible payment options:

  • Pay monthly holidays: Realise your holiday dreams sooner with Klarna's easy monthly instalment plans. If making bite-sized repayments each month works for you, pick this option during the checkout process.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna allows you to pay off your trip over multiple transactions.
  • Low deposit holidays: Clicking on the "book now" button is easier with this plan. Just put down a small deposit on your escape and then get on your way.

Where should I stay in Glenwood?
Most visitors to Glenwood include both Millennium Park and Wrigley Field on their must-see lists. Why not select a hotel that's close to these top attractions?
What are the top hotels in Glenwood?
If it's your first time in Glenwood, book a room at Hyatt Regency Chicago or The Godfrey Hotel Chicago. Both offer comfy beds and are top options with many savvy travellers.
How far in advance should I book my Glenwood holiday?
Search Expedia to compare international airfares as soon as you've got your travel dates. You can usually purchase a ticket up to a year in advance. If it's too early for your preferred air carrier, or you've left things to the last minute, don't worry. Low prices to Glenwood sometimes appear just weeks before departure.
What does an Expedia Glenwood travel package include?
Hotels, flights and a shiny set of wheels for all your road trip adventures. Simply choose your favourite bundle and get access to great discounts. Once you've made your booking, add on a couple of experiences and tours and watch your savings grow. When it comes to creating your Glenwood escape, the choice is all yours!
What should I know before booking a Glenwood travel package?
You'll save big with an Expedia travel package. Combine your airfares, rental cars and hotels and enjoy fabulous discounts. Hotels aren't your only choice, though. Book with us and choose from beachfront villas, rural cottages and even castles and houseboats!
Can I choose my airline with a Glenwood Expedia travel package?
Expedia offers access to more than 550 airline partners globally, so you sure can! Simply pick your preferred carrier and put together your ideal Glenwood trip.

* 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.