Glenwood Holidays from AU$1,876

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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.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
per person
2 Mar - 9 Mar
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (3,575 reviews)
Perfect location and an exceptional hotel!

Reviewed on 7 Jan. 2025

Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
2 Mar - 9 Mar
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (1,005 reviews)
We liked how attentive thw staff was. My date had a tag still attatched to him that we missed while heading out for brunch and shopping and the gentleman at the desk waived him over and let him know. Paid attention to the guest. We will definitely be back. Great staff

Reviewed on 6 Jan. 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
per person
2 Mar - 9 Mar
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.2/10 Wonderful! (1,253 reviews)
Always friendly and clean hotel. Love the club access on the too floor.

Reviewed on 5 Jan. 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
2 Mar - 9 Mar
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (1,469 reviews)
The view for the fireworks was amazing! I didn't like the fact that my wife and I both woke up with some kind of bug bites on our lower legs and on top of our feet!

Reviewed on 7 Jan. 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
2 Mar - 9 Mar
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (1,259 reviews)
Clean and convenient location.

Reviewed on 8 Jan. 2025

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

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$90 per night from 16 Jan to 17 Jan
AU$90
includes taxes & fees
16 Jan - 17 Jan
6.8/10 (1,074 reviews)
Good place for a quick stay.
"It was a place to sleep, no amenities and breakfast was not much. They did have the waffle machine so my husband was pleased. Comfortable bed, though not a mid or upper spend. It served our needs for the time needed."

Reviewed on 4 Jan. 2025

Motel 6 Bridgeview, IL
Sleep Inn Midway Airport Bedford Park
Sleep Inn Midway Airport Bedford Park
2.5 out of 5
6650 S Cicero Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$157 per night from 10 Jan to 11 Jan
AU$157
includes taxes & fees
10 Jan - 11 Jan
7.6/10 Good! (1,313 reviews)
"Great value for the price. Not top of the line, but neat and clean, and staff is polite and friendly. Convenient to walkable restaurants."

Reviewed on 6 Jan. 2025

Sleep Inn Midway Airport Bedford Park
Hyatt Place Chicago Midway Airport
Hyatt Place Chicago Midway Airport
3 out of 5
6550 S Cicero Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$239 per night from 14 Jan to 15 Jan
AU$239
includes taxes & fees
14 Jan - 15 Jan
9/10 Wonderful! (1,045 reviews)
"Good breakfast options Juice is a little watery"

Reviewed on 5 Jan. 2025

Hyatt Place Chicago Midway Airport
See all 759 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$1,876 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.