Glenwood Holidays from £939
Book a Hotel + Flight or Car together to unlock savings
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- Better togetherSave up to £750 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages with flights are ATOL protected
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.
Level Chicago – Old Town
Downtown Chicago
£1,116
per person
3 Nov - 8 Nov
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (527 reviews)
The location is perfect and the building is quite nice. The rooms are also comfortable. This is not a hotel, but rather occupies several floors in a large apartment building. We had a couple issues with our room (malfunctioning, smoke alarm and empty body wash) and neither were dealt with despite a asking multiple times.
Reviewed on 27 Sept 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
Sleep Inn Midway Airport Bedford Park
6650 S Cicero Ave Chicago IL
Fully refundableReserve now, pay when you stay
£94
25 Oct - 26 Oct
includes taxes & fees
8/10 Very good! (2,138 reviews)
"Staff was great, even gave me water bottles when I checked out for no charge but the beds had bed bugs I’m pretty sure since I left I’ve been itchy all day."
Reviewed on 27 Sept 2026
Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
£150
29 Sept - 30 Sept
includes taxes & fees
Holiday Inn Chicago – Midway Airport S by IHG
7353 S Cicero Avenue Chicago IL
Fully refundable
£131
27 Oct - 28 Oct
includes taxes & fees
8/10 Very good! (1,008 reviews)
"Broken toilet seat. Found out late, after almost getting injured. All lights have switches, hard to locate. I had no breakfast paid ahead.. not set up at 645 am. paided 5o. online then signed up repay again at hotel 26.00."
Reviewed on 27 Sept 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.
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 £939. 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.
