Hotel Cancun Rosa - Vacation Rentals in Far Southwest Side

Days Inn by Wyndham Calumet Park From US $103
         

10.0 (1 Review)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
DoubleTree by Hilton Chicago Midway Airport From US $263
         

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9.2 (1000 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Luxury Places to Stay in Far Southwest Side

Over 564+ Luxury Places to Stay in or Near Far Southwest Side
Wonderful 2-bedroom apartment with AC in lovely Alsip From US $1,467
         

New
Apartment
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Gorgeous 5 Bedroom Gem Sleeps 18 with Pool, Ping Pong, Pac Man, Tons of Games! From US $962
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Designated Smoking Area
Parisian Retreat 6min to Main Quandrangle U of C From US $870
         

9.7 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Security/Safety
The Brown House - A luxurious UChicago Campus stay From US $686
         

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10.0 (5 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Security/Safety

Top-Rated Vacation Rentals with a Pool in Far Southwest Side

Over 21+ Top-Rated Vacation Rentals with a Pool in or Near Far Southwest Side
Hyatt Place Chicago Midway Airport From US $210
         

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9.0 (1228 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Residence Inn Marriott Chicago Midway From US $247
         

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8.8 (642 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
DoubleTree by Hilton Chicago Midway Airport, IL From US $198
         

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8.8 (163 Reviews)
Hotel
  • Air Conditioner
  • Pool
  • Designated Smoking Area
Residence Inn Chicago Midway Airport From US $217
         

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8.8 (99 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Hyatt Place Chicago Midway Airport From US $181
         

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8.6 (769 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Hilton Chicago/Oak Lawn From US $178
         

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8.4 (1366 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
DoubleTree by Hilton Chicago - Alsip From US $147
         

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8.4 (1110 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Hilton Garden Inn Chicago/Midway Airport From US $192
         

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8.4 (1010 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Far Southwest Side

Over 175+ Pet-Friendly Vacation Rentals in or Near Far Southwest Side
Charming 3-bedroom apartment in superb Chicago with WiFi From US $207
         

10.0 (5 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxe Loft vibe with King Suite - 4BR 3Ba From US $405
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Red Roof Inn Chicago - Alsip From US $81
         

6.2 (689 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Cozy & Near Downtown, Hyde Park & the Metra From US $225
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
3BR Monthly Rental Near Midway Airport/Downtown From US $184
         

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

Large Vacation Homes & Villas in Far Southwest Side

Over 82+ Large Vacation Homes & Villas in or Near Far Southwest Side
Woodlawn Oasis.10 Minutes to Dining & Downtown From US $580
         

9.2 (14 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
LaSalle Lodge II From US $19
         

5.8 (62 Reviews)
Hostel
  • Parking
  • Child Friendly
  • Internet
Large 5BR Retreat. Perfect for Long Stays & Groups From US $582
         

Charming 2-bedroom apartment in marvelous Blue Island with WiFi From US $341
         

8.0 (6 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Cozy 5BR Chicago Retreat Sleeps 10 From US $492
         

7.4 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

Wheelchair Accessible Vacation Homes in Far Southwest Side

Over 37+ Wheelchair Accessible Vacation Homes in or Near Far Southwest Side
Chateau de Woodlawn - Peaceful 3 bedroom apartment. From US $126
         

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8.9 (15 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Stylish 4BR South Loop Home From US $520
         

10.0 (2 Reviews)
Apartment
  • TV
  • Wheelchair Accessible
  • Accessibility
Chateau de Woodlawn - Room III - The Dream Catcher From US $73
         

Hampton Inn by Hilton Chicago-Midway Airport From US $195
         

8.6 (1266 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Best Western Inn & Suites - Midway Airport From US $145
         

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8.2 (470 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Chicago Marriott Midway From US $234
         

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8.4 (981 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Far Southwest Side Vacation Rentals and Airbnb Places to Stay Under $200

Over 272+ Far Southwest Side Vacation Rentals and Airbnb Places to Stay Under $200
Cozy Urban Retreat Near Midway – Perfect for Travelers! From US $185
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • TV
  • Balcony/Terrace
Afrique Francaise de Woodlawn 1 From US $86
         

9.3 (13 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Bluestar Motel From US $103
         

8.6 (118 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area

Instantly Bookable Vacation Homes in Far Southwest Side

Over 225+ Instantly Bookable Vacation Homes in or Near Far Southwest Side
High-end 2Bdrm Garden Apt. Where Comfort Meets Style From US $255
         

10.0 (5 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Cozy 3BR Near Obama Presidential Center, Hyde Park & UChicago From US $341
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Security/Safety
Chicago Home Near Navy Pier & Shedd Aquarium! From US $247
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Superb townhome with Near Lake in vibrant Chicago From US $244
         

2 Mi to Calumet Park & Beach: Windy City Escape! From US $346
         

About Far Southwest Side Vacation Rentals

With more than 72 Far Southwest Side vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Hotelcancunrosa 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 Far Southwest Side.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Hotelcancunrosa Far Southwest Side, 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 Far Southwest Side. Places to stay near Far Southwest Side are 142.65 ft² on average, with prices averaging US $141 a night.

Hotelcancunrosa makes it easy and safe to find and compare vacation rentals in Far Southwest Side 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 Far Southwest Side

Type Count
Hotels 72

Use these Quick Filters to Find a Vacation Rental in Far Southwest Side

Pro Tip: Hotelcancunrosa makes it easy to compare the best listings on Hotelcancunrosa homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Hotelcancunrosa 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 Far Southwest Side.

Weather in Far Southwest Side

View the weather forecast for Far Southwest Side before booking your Far Southwest Side 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

Far Southwest Side Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Far Southwest Side?
How many vacation rentals are available in Far Southwest Side?

Currently, the total number of properties listed in 2026 is over 72 in the Far Southwest Side area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Far Southwest Side.