1521+ Private Villas and Holiday Rentals in Armour Square |
Armour Square Holiday Rentals
New
Apartment
1 Bedroom
1 Bath
2 Guests
500 ft²
Fireplace/Heating
Kitchen
Air Conditioner
Internet
US $474/Night
7 Nights - US $3,318
Apartment
10.0Exceptional
(4 Reviews)
13 Bedrooms
12 Baths
32 Guests
1435.19 ft²
Private Pool
Hot Tub- Fireplace/Heating
Pool
US $1,582/Night
7 Nights - US $11,076
House
- Chicago
- ·
- Bronzeville
- 0.16 mi to center
8.6Fabulous
(89 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
Balcony/Terrace- Kitchen
Parking
US $190/Night
7 Nights - US $1,331
New
Apartment
1 Bedroom
1 Bath
2 Guests
500 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $434/Night
7 Nights - US $3,037
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
10.0Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
8 Guests
8611.13 ft²
- Fireplace/Heating
Pet Friendly- Parking
- Air Conditioner
US $443/Night
7 Nights - US $3,103
Apartment
- Chicago
- ·
- Bridgeport
- 0.64 mi to center
2 Bedrooms
1 Bath
3 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $223/Night
7 Nights - US $1,558
New
Apartment
- Chicago
- ·
- Bronzeville
- 0.52 mi to center
3 Bedrooms
2 Baths
5 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
Child Friendly
US $149/Night
7 Nights - US $1,043
New
Hotel
- Chicago
- ·
- Near South Side
- 0.54 mi to center
2 Baths
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
Unlock the Best Price
New
Hotel
- Chicago
- ·
- South Loop
- 0.55 mi to center
2 Baths
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $1,318/Night
7 Nights - US $9,224
Luxury Holiday Rentals in Armour Square
Over 1512+ Luxury Holiday Rentals in or Near Armour Square
New
Hotel
- Chicago
- ·
- Near South Side
- 0.48 mi to center
3 Baths
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
Unlock the Best Price
New
Apartment
2 Bedrooms
2 Baths
8 Guests
1205.56 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
US $6,350/Night
7 Nights - US $44,450
Condo
10.0Exceptional
(3 Reviews)
10 Bedrooms
9 Baths
16 Guests
3337 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $3,563/Night
7 Nights - US $24,944
Condo
9 Bedrooms
5 Baths
16 Guests
2831 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $2,931/Night
7 Nights - US $20,514
Apartment
- Chicago
- ·
- South Loop
- 0.39 mi to center
8.8Fabulous
(4 Reviews)
2 Bedrooms
2 Baths
13 Guests
1001.04 ft²
- Fireplace/Heating
- Parking
- Air Conditioner
- Internet
US $2,671/Night
7 Nights - US $18,695
Apartment
10.0Exceptional
(1 Review)
5 Bedrooms
6 Baths
16 Guests
3165 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $2,656/Night
7 Nights - US $18,592
New
Hotel
- Chicago
- ·
- Near South Side
- 0.34 mi to center
5 Baths
1575.84 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
US $2,250/Night
7 Nights - US $15,750
Apartment
- Chicago
- ·
- Printers Row
- 0.12 mi to center
5 Bedrooms
5 Baths
14 Guests
2368 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $2,218/Night
7 Nights - US $15,526
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
5 Bedrooms
4 Baths
12 Guests
2303.48 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $2,198/Night
7 Nights - US $15,383
Top-Rated Holiday Rentals with a Pool in Armour Square
Over 220+ The Best Private Villas and Holiday Rentals in Armour Square with a Pool
Apartment
10.0Exceptional
(1 Review)
3 Bedrooms
3 Baths
6 Guests
1086 ft²
- Fireplace/Heating
- Pool
- Kitchen
- Parking
US $717/Night
7 Nights - US $5,017
Apartment
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
499 ft²
- Fireplace/Heating
- Pool
- Pet Friendly
- Kitchen
US $225/Night
7 Nights - US $1,575
Apartment
9.8Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
5 Guests
882.64 ft²
- Fireplace/Heating
- Pool
- Air Conditioner
- Internet
US $767/Night
7 Nights - US $5,366
House
- Chicago
- ·
- Bronzeville
- 0.38 mi to center
9.4Exceptional
(3 Reviews)
3 Bedrooms
1 Bath
6 Guests
1500 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $338/Night
7 Nights - US $2,366
Apartment
9.2Exceptional
(1174 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $358/Night
7 Nights - US $2,504
Hotel
9.2Exceptional
(1003 Reviews)
1 Bath
- Hot Tub
Spa- Fireplace/Heating
- Pool
US $331/Night
7 Nights - US $2,317
Hotel
- Chicago
- ·
- Near South Side
- 0.41 mi to center
9.2Exceptional
(849 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
Breakfast
US $374/Night
7 Nights - US $2,619
Apartment
9.2Exceptional
(5 Reviews)
2 Bedrooms
2 Baths
5 Guests
882.64 ft²
- Fireplace/Heating
- Pool
- Air Conditioner
- Internet
US $312/Night
7 Nights - US $2,182
Hotel
- Chicago
- ·
- Near South Side
- 0.40 mi to center
9.0Exceptional
(1008 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
US $190/Night
7 Nights - US $1,329
Pet-Friendly Holiday Rentals in Armour Square
Over 572+ Pet-Friendly Holiday Rentals in or Near Armour Square
Condo
- Chicago
- ·
- South Loop
- 0.68 mi to center
10.0Exceptional
(13 Reviews)
2 Bedrooms
2 Baths
5 Guests
689 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $604/Night
7 Nights - US $4,230
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
10.0Exceptional
(3 Reviews)
6 Bedrooms
4 Baths
12 Guests
1851.39 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $1,136/Night
7 Nights - US $7,951
Apartment
9.6Exceptional
(442 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $186/Night
7 Nights - US $1,302
Condo
- Chicago
- ·
- South Loop
- 0.39 mi to center
10.0Exceptional
(12 Reviews)
2 Bedrooms
3 Baths
6 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $618/Night
7 Nights - US $4,323
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
10.0Exceptional
(3 Reviews)
2 Bedrooms
2 Baths
8 Guests
796.53 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $434/Night
7 Nights - US $3,041
Apartment
- Chicago
- ·
- Printers Row
- 0.13 mi to center
10.0Exceptional
(11 Reviews)
2 Bedrooms
2 Baths
7 Guests
1109 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $747/Night
7 Nights - US $5,229
Apartment
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
12 Guests
969 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $426/Night
7 Nights - US $2,980
Apartment
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
583 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $310/Night
7 Nights - US $2,170
Apartment
9.8Exceptional
(75 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $598/Night
7 Nights - US $4,185
Large Holiday Rentals and Private Villas in Armour Square
Over 206+ Large Holiday Rentals and Private Villas in or Near Armour Square
Apartment
- Chicago
- ·
- South Loop
- 0.39 mi to center
9.0Exceptional
(26 Reviews)
2 Bedrooms
2 Baths
13 Guests
1000 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $331/Night
7 Nights - US $2,317
Apartment
- Chicago
- ·
- Near South Side
- 0.71 mi to center
10.0Exceptional
(2 Reviews)
4 Bedrooms
3 Baths
10 Guests
1937.5 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
US $772/Night
7 Nights - US $5,404
Apartment
3 Bedrooms
1 Bath
10 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $309/Night
7 Nights - US $2,163
Apartment
- Chicago
- ·
- Back of the Yards
- 0.61 mi to center
1 Bedroom
1 Bath
16 Guests
- Air Conditioner
- Child Friendly
Security/Safety
US $167/Night
7 Nights - US $1,171
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
10.0Exceptional
(1 Review)
6 Bedrooms
3 Baths
12 Guests
2723.27 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $1,181/Night
7 Nights - US $8,267
Apartment
10.0Exceptional
(22 Reviews)
4 Bedrooms
4 Baths
10 Guests
1350 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $1,014/Night
7 Nights - US $7,097
Apartment
- Chicago
- ·
- Armour Square
- 0.77 mi to center
10.0Exceptional
(22 Reviews)
4 Bedrooms
1 Bath
11 Guests
1100 ft²
- Kitchen
- Parking
- Internet
- Child Friendly
US $447/Night
7 Nights - US $3,131
House
10.0Exceptional
(19 Reviews)
5 Bedrooms
4 Baths
8 Guests
- Fireplace/Heating
Ocean View- Balcony/Terrace
View
US $725/Night
7 Nights - US $5,078
Condo
10.0Exceptional
(16 Reviews)
4 Bedrooms
2 Baths
20 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $516/Night
7 Nights - US $3,613
Wheelchair Accessible Holiday Homes in Armour Square
Over 699+ Wheelchair Accessible Holiday Homes in or Near Armour Square
New
Hotel
2 Baths
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $1,108/Night
7 Nights - US $7,757
House
- Chicago
- ·
- Near South Side
- 0.88 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
2 Baths
8 Guests
1797.57 ft²
- Fireplace/Heating
- View
- Pet Friendly
- Air Conditioner
US $441/Night
7 Nights - US $3,089
Hotel
9.6Exceptional
(1259 Reviews)
1 Bath
- Breakfast
- Kitchen
- Parking
- Air Conditioner
US $248/Night
7 Nights - US $1,739
New
Hotel
- Chicago
- ·
- Near South Side
- 0.45 mi to center
4 Baths
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $985/Night
7 Nights - US $6,895
House
- Chicago
- ·
- Near South Side
- 0.88 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
2 Baths
8 Guests
1797.57 ft²
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $351/Night
7 Nights - US $2,454
New
Hotel
- Chicago
- ·
- Near South Side
- 0.47 mi to center
3 Baths
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $985/Night
7 Nights - US $6,893
New
Hotel
- Chicago
- ·
- South Loop
- 0.54 mi to center
2 Baths
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $740/Night
7 Nights - US $5,178
New
Hotel
- Chicago
- ·
- Printers Row
- 0.14 mi to center
2 Baths
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $668/Night
7 Nights - US $4,676
Hotel
- Chicago
- ·
- South Loop
- 0.72 mi to center
2 Baths
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $654/Night
7 Nights - US $4,578
Armour Square Private Villas and Holiday Homes Under $200
Over 436+ Armour Square Private Villas and Holiday Homes Under $200
Apartment
- Chicago
- ·
- Heart of Chicago
- 0.16 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $175/Night
7 Nights - US $1,224
Apartment
- Chicago
- ·
- Grand Boulevard
- 0.60 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
5 Guests
9687.52 ft²
- Air Conditioner
- Internet
- Child Friendly
US $180/Night
7 Nights - US $1,260
House
- Chicago
- ·
- Bronzeville
- 0.35 mi to center
7.8Very Good
(60 Reviews)
1 Bedroom
1 Bath
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $120/Night
7 Nights - US $840
Apartment
- Chicago
- ·
- Grand Boulevard
- 0.54 mi to center
9.8Exceptional
(102 Reviews)
1 Bedroom
1 Bath
5 Guests
1000 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $138/Night
7 Nights - US $966
Apartment
- Chicago
- ·
- Grand Boulevard
- 0.60 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
4 Guests
904.17 ft²
- Balcony/Terrace
- Parking
- Air Conditioner
- Internet
US $114/Night
7 Nights - US $798
Apartment
- Chicago
- ·
- Grand Boulevard
- 0.52 mi to center
9.6Exceptional
(76 Reviews)
2 Bedrooms
1 Bath
8 Guests
1600 ft²
- Fireplace/Heating
- Ocean View
- View
- Kitchen
US $174/Night
7 Nights - US $1,215
Apartment
9.6Exceptional
(4 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Air Conditioner
- Child Friendly
Laundry
US $171/Night
7 Nights - US $1,195
House
- Chicago
- ·
- Heart of Chicago
- 0.11 mi to center
9.0Exceptional
(11 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $188/Night
7 Nights - US $1,317
Apartment
- Chicago
- ·
- Bridgeport
- 0.29 mi to center
8.6Fabulous
(16 Reviews)
1 Bedroom
1 Bath
4 Guests
1200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $176/Night
7 Nights - US $1,235
Instantly Bookable Holiday Homes in Armour Square
Over 877+ Instantly Bookable Holiday Homes in or Near Armour Square
New
Hotel
- Chicago
- ·
- Near South Side
- 0.81 mi to center
2 Baths
800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $639/Night
7 Nights - US $4,473
Bed & Breakfast
- Chicago
- ·
- Bronzeville
- 0.16 mi to center
2.0Average
(1 Review)
1 Bedroom
1 Bath
2 Guests
237 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $194/Night
7 Nights - US $1,357
New
Hotel
- Chicago
- ·
- Printers Row
- 0.22 mi to center
2 Baths
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $634/Night
7 Nights - US $4,440
New
Hotel
2 Baths
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $632/Night
7 Nights - US $4,426
New
Hotel
- Chicago
- ·
- Printers Row
- 0.10 mi to center
2 Baths
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $627/Night
7 Nights - US $4,388
New
Hotel
- Chicago
- ·
- Near South Side
- 0.48 mi to center
2 Baths
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $458/Night
7 Nights - US $3,203
New
Hotel
- Chicago
- ·
- Near South Side
- 0.42 mi to center
2 Baths
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $389/Night
7 Nights - US $2,720
New
Hotel
- Chicago
- ·
- Near South Side
- 0.48 mi to center
2 Baths
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $373/Night
7 Nights - US $2,608
New
Hotel
- Chicago
- ·
- Prairie District
- 0.13 mi to center
2 Baths
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $349/Night
7 Nights - US $2,444
Book a Last Minute Place to Stay in Armour Square
About Casai's Private Villas and Holiday Rentals in Armour Square
Discover more than 1521 vacation rentals available in Armour Square. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Armour Square.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Armour Square, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Armour Square. On average, places to stay near Armour Square offer 825.28 ft², with nightly prices averaging US $466.
With Casai, finding and comparing holiday rentals in Armour Square is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Armour Square
| Type | Count |
|---|---|
| Holiday Apartments | 1097 |
| Vacation Homes | 134 |
| Villas | 2 |
| Cottages | 1 |
Use these Quick Filters to Find a Holiday Rental in Armour Square
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Armour Square.
Weather in Armour Square, IL
View the weather forecast for Armour Square before booking your Armour Square 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
Frequently Asked Questions About Armour Square?
What are the top holiday rentals in Armour Square?
With numerous options available in Armour Square, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Armour Square:
- Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
- Vibrant 3BR Pilsen Stay Free Parking Near Downtown
- Modern West Loop Gem-City Views & Prime Location 6
- 4 #1S - 4 Bedroom/1.5 Bath Condo near McCormick Place, Wintrust Arena
- Luxury Hyde Park Haven- Perfect for families and digital nomads. Pet Friendly.
- Luxury Modern home minutes from Downtown Chicago
- Gorgeous historic mansion on UChicago campus. Renovation with original detail.
- Penthouse, Lux stay near Downtown, McComick & Lake
- 1 #33 - 4 Bedroom/2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown
- Dtown Penthouse 3bd VIEWS+Parking +Gym+Pool
How many holiday rentals have private pools in Armour Square?
Discover a selection of holiday rentals with private pools near Armour Square with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
- Spacious 1 bd sleeps 4 quiet and near Michigan Ave. free gift
- Jeffjack Heated Pool Penthouse in Chicago's West Loop
- S Loop 1BR w Pool Gym nr Museum Campus CHI-352
- S Loop 2BR w Pool Gym Spa nr Grant Park CHI-740
Which holiday homes in Armour Square are best for families?
If you're searching for a family-friendly holiday home in Armour Square, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Armour Square:
- Cozy smoking Suite Downtown McCormick Lakefront
- Spacious 2BR South Loop Suite with Skyline View, Optional Parking and Gym Access Close to McCormick Place, Grant Park, Museum Campus & CTA Lines
- Stylish Apartment near Chicago Downtown
How many Casai.com holiday rentals are available in Armour Square?
As of 2026, Casai boasts over 1521 properties listed in the Armour Square area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Armour Square.
Nearby Neighborhood (5)
| Neighborhood | Property Count |
|---|---|
| Douglas Vacation Rentals in Chicago, Illinois | 39 |
| Bridgeport Vacation Rentals in Chicago, Illinois | 1590 |
| Chinatown Vacation Rentals in Chicago, Illinois | 3132 |
| Ickes Praire Homes Vacation Rentals in Chicago, Illinois | 2101 |
| Dearborn Homes Vacation Rentals in Chicago, Illinois | 1673 |
People Also Ask
Finding the best prices in Armour Square
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