Wing Foil Vacations - Vacation Rentals in Glendale

Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10 From US $271
         

Amazing Place to stay near Downtown Chicago! From US $100
         

DoubleTree by Hilton Chicago Midway Airport From US $169
         

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9.2 (1003 Reviews)
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Stylish comfortable 3BR with tons of natural light From US $265
         

Cozy 3 Bedroom Family Sized Duplex/9 mins from Midway airport!nn From US $286
         

10.0 (1 Review)
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Cozy Urban Retreat Near Midway – Perfect for Travelers! From US $194
         

10.0 (1 Review)
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  • TV
  • Balcony/Terrace
3BR Monthly Rental Near Midway Airport/Downtown From US $192
         

10.0 (1 Review)
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  • Air Conditioner
  • Pet Friendly
  • TV

Luxury Places to Stay in Glendale

Over 91+ Luxury Places to Stay in or Near Glendale
Spacious 5-bedroom bungalow in delightful Chicago with AC, WiFi From US $394
         

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Smokers Preferred-Spacious 3-bedroom apartment with WiFi, AC in awesome Chicago From US $339
         

8.0 (3 Reviews)
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Hampton Inn Chicago-Midway Airport From US $339
         

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7.9 (317 Reviews)
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Slick, Modern Retreat Near Downtown Sleeps 8 From US $335
         

Your Home Away from home -12 mins from Downtown From US $312
         

9.4 (3 Reviews)
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W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade From US $286
         

Top-Rated Vacation Rentals with a Pool in Glendale

Over 13+ Top-Rated Vacation Rentals with a Pool in or Near Glendale
Hyatt Place Chicago Midway Airport From US $189
         

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9.0 (1190 Reviews)
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Residence Inn Chicago Midway Airport From US $217
         

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8.9 (97 Reviews)
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Residence Inn Marriott Chicago Midway From US $194
         

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8.8 (618 Reviews)
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DoubleTree by Hilton Chicago Midway Airport, IL From US $198
         

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8.8 (165 Reviews)
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  • Pool
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Hyatt Place Chicago Midway Airport From US $181
         

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8.6 (769 Reviews)
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Hilton Garden Inn Chicago/Midway Airport From US $179
         

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8.4 (1004 Reviews)
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Chicago Marriott Midway From US $189
         

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8.4 (947 Reviews)
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Courtyard by Marriott Chicago Midway Airport From US $179
         

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8.2 (1006 Reviews)
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Pet-Friendly Vacation Rentals in Glendale

Over 26+ Pet-Friendly Vacation Rentals in or Near Glendale
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6 From US $211
         

8.6 (21 Reviews)
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  • Pet Friendly
Sleep Inn Midway Airport From US $116
         

7.8 (620 Reviews)
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Small hidden Gem. Location! From US $138
         

8.6 (17 Reviews)
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Charming 2-bedroom apartment in fabulous Chicago with WiFi, Game Space From US $206
         

Stylish & Comfy Stay: Close to Downtown From US $101
         

4.0 (1 Review)
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Large Group Home From US $228
         

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Chic & Cozy Chicago Stay Close to Downtown From US $107
         

See More Pet-Friendly Vacation Rentals in Glendale on PetFriendly.io

Large Vacation Homes & Villas in Glendale

Over 5+ Large Vacation Homes & Villas in or Near Glendale
Spacious 4-bedroom apartment with AC and WiFi in terrific Chicago From US $243
         

Beautiful Apartment in Chicago From US $167
         

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Dalia Flat - Sleeps 10 - 10 minutes to Downtown From US $238
         

8.8 (15 Reviews)
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Wheelchair Accessible Vacation Homes in Glendale

Over 9+ Wheelchair Accessible Vacation Homes in or Near Glendale
Holiday Inn Express & Suites Chicago-Midway Airport by IHG From US $199
         

8.0 (280 Reviews)
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Fairfield Inn & Suites Chicago Midway Airport From US $149
         

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7.8 (271 Reviews)
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  • Pet Friendly
Hampton Inn by Hilton Chicago-Midway Airport From US $169
         

8.6 (1247 Reviews)
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Hilton Garden Inn Chicago/Midway Airport From US $220
         

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7.6 (260 Reviews)
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Sleep Inn Midway Airport Bedford Park From US $133
         

8.0 (1847 Reviews)
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Courtyard Chicago Midway Airport From US $230
         

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7.5 (205 Reviews)
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Carlton Inn Midway From US $99
         

5.1 (705 Reviews)
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Glendale Vacation Rentals and Airbnb Places to Stay Under $200

Over 35+ Glendale Vacation Rentals and Airbnb Places to Stay Under $200
Condo Apartment Near Midway Airport From US $139
         

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8.9 (13 Reviews)
Apartment
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Carlton Inn Midway From US $115
         

6.2 (1005 Reviews)
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Chicago Midway Oasis From US $171
         

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Updated Spacious 2-bedroom apartment in charming Chicago From US $155
         

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8 Minutes from Midway Airport! From US $149
         

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Instantly Bookable Vacation Homes in Glendale

Over 24+ Instantly Bookable Vacation Homes in or Near Glendale
Cozy 2- bedroom w/patio mins from Midway Airport From US $205
         

9.8 (12 Reviews)
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  • TV
Luxurious 3Br with parking on premises 🌔 From US $250
         

9.2 (14 Reviews)
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  • Air Conditioner
  • Parking
  • TV
Charming 2-bedroom townhome in brilliant Chicago with WiFi, AC From US $286
         

10.0 (1 Review)
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  • Pet Friendly
  • Security/Safety
2-bedroom apartment in charming Chicago with WiFi, AC From US $228
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Security/Safety
  • Fireplace/Heating
5 minutes from Midway Int'l Airport Single Family Home. From US $219
         

9.4 (6 Reviews)
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  • Balcony/Terrace
Style. Culture. History. Affordable City Living. Gorgeous Stain Glass Windows. From US $92
         

Chic & Cozy Chicago Stay: Close to Downtown From US $107
         

4.0 (1 Review)
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  • Air Conditioner
  • Parking
  • Pet Friendly

About Glendale Vacation Rentals

With more than 100 Glendale vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Wingfoilvacations and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Glendale.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Wingfoilvacations Glendale, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Glendale. Places to stay near Glendale are 267.47 ft² on average, with prices averaging US $195 a night.

Wingfoilvacations makes it easy and safe to find and compare vacation rentals in Glendale with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Glendale

Type Count
Holiday Apartments 51
Hotels 24
Vacation Homes 23

Use these Quick Filters to Find a Vacation Rental in Glendale

Pro Tip: Wingfoilvacations makes it easy to compare the best listings on Wingfoilvacations homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Wingfoilvacations homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Glendale.

Weather in Glendale

View the weather forecast for Glendale before booking your Glendale Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Glendale Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Glendale?
How many vacation rentals are available in Glendale?

Currently, the total number of properties listed in 2026 is over 100 in the Glendale area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Glendale.