Wintersvacationsrentals - Vacation Rentals in Central Chicago

Property Image From US $735
         

10.0 (119 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Property Image From US $1,516
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Property Image From US $73
         

9.0 (1035 Reviews)
Hostel
  • Air Conditioner
  • Wheelchair Accessible
  • Accessibility
Property Image From US $280
         

Property Image From US $254
         

Property Image From US $812
         

10.0 (300 Reviews)
Apartment
  • Air Conditioner
  • Pool
  • TV
Property Image From US $283
         

Property Image From US $553
         

Luxury Places to Stay in Central Chicago

Over 2698+ Luxury Places to Stay in or Near Central Chicago
Property Image From US $4,163
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Property Image From US $3,806
         

New
Resort
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Property Image From US $3,584
         

New
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible

Top-Rated Vacation Rentals with a Pool in Central Chicago

Over 869+ Top-Rated Vacation Rentals with a Pool in or Near Central Chicago
Property Image From US $242
         

10.0 (61 Reviews)
Apartment
  • Air Conditioner
  • Pool
  • TV
Property Image From US $250
         

Property Image From US $624
         

10.0 (12 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From US $495
         

10.0 (7 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From US $429
         

10.0 (7 Reviews)
Apartment
  • Air Conditioner
  • Pool
  • TV

Pet-Friendly Vacation Rentals in Central Chicago

Over 1253+ Pet-Friendly Vacation Rentals in or Near Central Chicago
Property Image From US $403
         

10.0 (6 Reviews)
Hotel
  • Air Conditioner
  • Pet Friendly
  • Wheelchair Accessible
Property Image From US $325
         

10.0 (24 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From US $563
         

10.0 (20 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From US $583
         

10.0 (19 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From US $132
         

10.0 (12 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From US $381
         

10.0 (9 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Central Chicago

Over 277+ Large Vacation Homes & Villas in or Near Central Chicago
Property Image From US $829
         

10.0 (105 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Property Image From US $1,582
         

|
10.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Property Image From US $784
         

Property Image From US $448
         

10.0 (16 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Property Image From US $476
         

10.0 (7 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From US $593
         

10.0 (6 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Wheelchair Accessible Vacation Homes in Central Chicago

Over 1881+ Wheelchair Accessible Vacation Homes in or Near Central Chicago
Property Image From US $249
         

10.0 (21 Reviews)
Condo
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Property Image From US $453
         

10.0 (3 Reviews)
Hotel
  • Air Conditioner
  • Wheelchair Accessible
  • Accessibility
Property Image From US $1,976
         

Property Image From US $437
         

10.0 (5 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
Property Image From US $586
         

10.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Property Image From US $537
         

Central Chicago Varoom and Airbnb Places to Stay Under $200

Over 961+ Central Chicago Varoom and Airbnb Places to Stay Under $200
Property Image From US $175
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From US $103
         

9.4 (7 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From US $107
         

7.0 (96 Reviews)
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

Instantly Bookable Vacation Homes in Central Chicago

Over 1719+ Instantly Bookable Vacation Homes in or Near Central Chicago
Property Image From US $412
         

10.0 (50 Reviews)
Condo
  • Air Conditioner
  • TV
  • Balcony/Terrace
Property Image From US $266
         

9.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Property Image From US $596
         

10.0 (24 Reviews)
Condo
  • Air Conditioner
  • TV
  • Security/Safety
Property Image From US $454
         

10.0 (10 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Property Image From US $240
         

10.0 (5 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From US $680
         

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

About Central Chicago Vacation Rentals

With more than 2707 Central Chicago vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Wintersvacationsrentals 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 Wintersvacationsrentals 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 734.02 ft² on average, with prices averaging $405 a night.

Wintersvacationsrentals 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 1661
Hotels with Suites 601
Vacation Homes 309
Resorts 26
Villas 4
Cabin Rentals 2
Hostels 2

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

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