Isle Of Palm Resorts - Vacation Rentals in Central Chicago

Magic Factory Loft 2East 4 Bd/3 Ba Families Groups From US $890
         

10.0 (119 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
New Luxury 3 Bdr Apt in Chicago C9 From US $1,516
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Chicago Avenue Inn From US $116
         

7.0 (101 Reviews)
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
52nd Floor MagMile Penthouse Views Fireplace Pool From US $324
         

10.0 (408 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
51st Floor MagMile Penthouse Views Balcony Pool From US $305
         

10.0 (227 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
55th Floor Penthouse with Award-Winning Views From US $941
         

10.0 (301 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
53 Floor MagMile Penthouse Views, Balcony, Pool From US $284
         

10.0 (244 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
2-Story Penthouse Views, Fireplace, Pool, Gym From US $615
         

10.0 (212 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool

Luxury Places to Stay in Central Chicago

Over 2820+ Luxury Places to Stay in or Near Central Chicago
Iconic Downtown Penthouses Getaway + City Views From US $3,603
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pool
South Loop 2 Bedroom Apt From US $2,671
         

New
Apartment
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Top-Rated Vacation Rentals with a Pool in Central Chicago

Over 912+ Top-Rated Vacation Rentals with a Pool in or Near Central Chicago
52nd Floor Penthouse with Skyline Views & Pool From US $307
         

10.0 (64 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
50th Floor Mag Mile VIEWS, Balcony, Pool, Gym From US $225
         

10.0 (32 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Dtown Penthouse 3bd VIEWS+Parking +Gym+Pool From US $446
         

10.0 (12 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxury Designer Penthouse 3804 | Pool | Gold Coast From US $591
         

10.0 (9 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
53-54 Floor Penthouse From US $574
         

10.0 (8 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Historic Charm + Modern Comfort for Tourists From US $564
         

10.0 (8 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Central Chicago

Over 1316+ Pet-Friendly Vacation Rentals in or Near Central Chicago
Kasa River North Chicago From US $256
         

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9.6 (182 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba From US $363
         

10.0 (26 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxury Loft Collection 703 - Terrace - River North From US $727
         

10.0 (22 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxury Loft Collection 02 - Terrace - River North From US $691
         

10.0 (20 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Tranquil Portage Park Stay From US $128
         

10.0 (14 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba From US $330
         

10.0 (10 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Spacious 4BR Central Apartment w/Skyline Views From US $260
         

10.0 (8 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV

Large Vacation Homes & Villas in Central Chicago

Over 299+ Large Vacation Homes & Villas in or Near Central Chicago
Lux Apts with Lake Views and Top Amenities From US $1,582
         

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10.0 (4 Reviews)
Apartment
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  • Pool
Magic Factory Loft 3East 4 Bd/4 Ba Families Groups From US $1,127
         

10.0 (106 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
City Center, River North Condo HUGE 3BR, Patio, Parking(2x) From US $788
         

Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow From US $368
         

10.0 (18 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Luxury Loft Collection 903 - Terrace - River North From US $715
         

10.0 (7 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Wheelchair Accessible Vacation Homes in Central Chicago

Over 1989+ Wheelchair Accessible Vacation Homes in or Near Central Chicago
Downtown Guild #3 | Mag Mile Gold Coast The Lake! From US $269
         

Stylish 3BR Gem in Prime Location From US $441
         

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10.0 (1 Review)
House
  • Air Conditioner
  • Pet Friendly
  • View
HI Chicago Hostel From US $73
         

9.0 (1112 Reviews)
Hostel
  • Air Conditioner
  • Wheelchair Accessible
  • Accessibility
Luxury Penthouse: Iconic Views + Exclusive Comfort From US $1,943
         

Luxury 2BR near Millennium Park + 5-Star Reviews From US $664
         

10.0 (5 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Luxury Loft Collection COMBO 01/02 | Terrace From US $1,262
         

10.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Penthouse Escape + Vibrant West Loop Access From US $913
         

10.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool

Central Chicago Varoom and Airbnb Places to Stay Under $200

Over 1083+ Central Chicago Varoom and Airbnb Places to Stay Under $200
Chic Studio in the Heart of the Gold Coast From US $166
         

10.0 (5 Reviews)
Apartment
  • Pet Friendly
  • TV
  • Security/Safety
UrbanEden Loft Apartment From US $103
         

9.4 (7 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
L7 Chicago by LOTTE From US $184
         

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9.6 (3594 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Downtown 2bd #6 +Gym near Park, Lake, Museums From US $191
         

10.0 (2 Reviews)
Condo
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Downtown 2bd #4 - Near Grant Park, Museums, Lake From US $184
         

10.0 (2 Reviews)
Condo
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Chic 1-bedroom condo in the heart of Chicago, next to Mag Mile From US $143
         

Chicago Cityview Chic - Gold Coast/River North From US $199
         

Instantly Bookable Vacation Homes in Central Chicago

Over 1843+ Instantly Bookable Vacation Homes in or Near Central Chicago
Brilliant Downtown Chicago 3-Bedroom Condominium From US $415
         

10.0 (50 Reviews)
Condo
  • Air Conditioner
  • TV
  • Balcony/Terrace
Twice as Nice: Chic 2BR Stay with Style & Space From US $266
         

9.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Gorgeous 3BR River North Condo - Free Parking From US $697
         

10.0 (30 Reviews)
Condo
  • Air Conditioner
  • TV
  • Security/Safety
2BR Retreat in Downtown + City Skyline Views From US $614
         

10.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Luxéry Stay "Chicago" Downtown/McCormick/Wintrust Area From US $543
         

About Central Chicago Vacation Rentals

With more than 2827 Central Chicago vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Isleofpalmsresorts 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 Central Chicago.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Isleofpalmsresorts Central Chicago, 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 Central Chicago. Places to stay near Central Chicago are 726.81 ft² on average, with prices averaging $394 a night.

Isleofpalmsresorts makes it easy and safe to find and compare vacation rentals in Central Chicago 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 Central Chicago

Type Count
Holiday Apartments 1794
Hotels with Suites 591
Vacation Homes 320
Resorts 25
Cabin Rentals 2
Villas 2
B&B 1

Use these Quick Filters to Find a Vacation Rental in Central Chicago

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

Weather in Central Chicago

View the weather forecast for Central Chicago before booking your Central Chicago 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