Glenwood Holidays from AU$3,688

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Your Glenwood Holiday

Let our holiday packages to Glenwood inspire your next great adventure. You'll find loads to love about this lively city, starting with the neighbourhood of South Deering, which is good for golfing and nature. You'll want to sightsee during your trip to Glenwood. Carve out some time for famous attractions like Coyote Run Golf Course, River Oaks Centre and Lansing Square Shopping Centre. Stop daydreaming and start travelling. Check out the wide range of options on Expedia today and finally put your Glenwood holiday plans in motion!

The Latest Glenwood Holiday Deals

Price found within the past 48 hours. Click for updated prices.
The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

4.5 out of 5
Downtown Chicago
Price was AU$4,440, price is now AU$3,688 per person
AU$3,688
per person
28 Dec - 3 Jan
found 8 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
8.8/10 Excellent! (2,580 reviews)

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was AU$7,537, price is now AU$5,906 per person
AU$5,906
per person
28 Dec - 3 Jan
found 8 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was AU$4,711, price is now AU$3,889 per person
AU$3,889
per person
28 Dec - 3 Jan
found 8 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9/10 Wonderful! (3,572 reviews)

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was AU$4,555, price is now AU$3,773 per person
AU$3,773
per person
28 Dec - 3 Jan
found 8 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (2,419 reviews)
Great.

Reviewed on 10 Nov 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was AU$4,446, price is now AU$3,695 per person
AU$3,695
per person
28 Dec - 3 Jan
found 8 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (185 reviews)

Glenwood Holiday

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 Munson Beach

Our pick of the best Glenwood Hotel Deals

Wind Creek Chicago Southland Casino and Hotel

Wind Creek Chicago Southland Casino and Hotel

4.5 out of 5
17300 S Halsted St Hazel Crest IL
Fully refundableReserve now, pay when you stay
The price is AU$234 per night from 24 Nov to 25 Nov
AU$234
24 Nov - 25 Nov
includes taxes & fees
Wind Creek Chicago Southland Casino and Hotel
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 AU$100 per night from 30 Nov to 1 Dec
AU$100
30 Nov - 1 Dec
includes taxes & fees
Motel 6 Bridgeview, IL
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 refundable
The price is AU$196 per night from 9 Dec to 10 Dec
AU$196
9 Dec - 10 Dec
includes taxes & fees
8/10 Very good! (1,000 reviews)
"Thank you,"

Reviewed on 10 Nov 2026

Holiday Inn Chicago – Midway Airport S by IHG
See all 977 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
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Glenwood holiday package cost?
You can pick up a holiday package to this top destination from AU$3,688 on Expedia. But how much your holiday to Glenwood costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Glenwood?
January, February and November are great times to look for cheap Glenwood holiday packages. Choosing to travel in quieter months means you can typically find reduced prices on hotels and flights.
How many days is enough for Glenwood?
With a well-planned itinerary, you can easily visit the main Glenwood sights in a handful of days. But if you'd like to discover lesser-known spots or go on day trips, consider booking your Glenwood holiday for longer.
How to find the best Glenwood package deals?
Use Expedia's filters to help you find some of the best Glenwood package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or browse for Glenwood package deals in the low season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your holiday package well in advance.
Is it cheaper to book a Glenwood holiday as a package?
Expedia holiday packages are designed to help you keep more money in your pocket. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll usually score a better deal than booking each component individually. And you'll still enjoy the flexibility to create a tailored Glenwood holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday package to Glenwood?
If you've got your Glenwood holiday dates finalized, book early to snap up some awesome deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spontaneous adventures? Our last-minute deals are great for quick escapes.
How to plan a trip to Glenwood?

  1. Pick the right time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to go to Glenwood.
  2. Set a budget: Factor in costs such as flights, food and transportation when calculating how much to put aside for your trip to Glenwood. Then, choose a hotel that fits your budget, whether that's a low-cost option or a deluxe retreat.
  3. Decide how many days away: Start by compiling a list of the activities and attractions you'd like to experience in Glenwood. Then, estimate how long you'll need for each, along with any travel time.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to pick a Glenwood holiday package that brings all your bookings together.

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