Chicago All-Inclusive Resorts, Hotels & Rentals

Plan Your Next Vacation to Chicago to Relax, Recharge & Re-imagine

Property Image From $238
         

10.0 (233 Reviews)
Apartment
  • Air Conditioner
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  • TV
Property Image From $7
         

3.0 (193 Reviews)
House
  • Parking
  • Child Friendly
  • Internet
Property Image From $254
         

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10.0
Bed & Breakfast
  • 904 ft² Bed & Breakfast
  • Parking
  • Security/Safety
  • Guest Services
Property Image From $309
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $276
         

Property Image From $299
         

Property Image From $614
         

10.0 (119 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Property Image From $112
         

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New
Apartment
  • Air Conditioner
  • Pet Friendly
  • Child Friendly

Luxury Places to Stay in Chicago

Over 6949+ Luxury Places to Stay in or Near Chicago
Property Image From $4,986
         

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New
House
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Property Image From $4,468
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Property Image From $4,055
         

Property Image From $3,806
         

New
Resort
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Property Image From $3,657
         

New
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible

Top-Rated Vacation Rentals with a Pool in Chicago

Over 1187+ Top-Rated Vacation Rentals with a Pool in or Near Chicago
Property Image From $311
         

Property Image From $1,001
         

10.0 (298 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Property Image From $313
         

Property Image From $375
         

Property Image From $599
         

Property Image From $837
         

Property Image From $664
         

Property Image From $375
         

10.0 (61 Reviews)
Apartment
  • Air Conditioner
  • Pool
  • TV

Pet-Friendly Vacation Rentals in Chicago

Over 2932+ Pet-Friendly Vacation Rentals in or Near Chicago
Property Image From $228
         

10.0 (38 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $130
         

6.3 (47 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Internet
Property Image From $250
         

New
Bed & Breakfast
  • 699 ft² Bed & Breakfast
  • Air Conditioner
  • Pet Friendly
  • TV
Property Image From $134
         

7.8 (602 Reviews)
Bed & Breakfast
  • Parking
  • Pet Friendly
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Property Image From $642
         

10.0 (108 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $338
         

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New
Apartment
  • Parking
  • Pet Friendly
  • Child Friendly
Property Image From $255
         

9.6 (184 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $107
         

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

Large Vacation Homes & Villas in Chicago

Over 854+ Large Vacation Homes & Villas in or Near Chicago
Property Image From $19
         

5.8 (62 Reviews)
Hostel
  • Parking
  • Child Friendly
  • Internet
Property Image From $188
         

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9.0 (7488 Reviews)
Hostel
  • Air Conditioner
  • Parking
  • Pool
Property Image From $930
         

9.8 (53 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Property Image From $1,582
         

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10.0 (4 Reviews)
Apartment
  • Air Conditioner
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  • Pool
Property Image From $762
         

10.0 (84 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $484
         

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10.0 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace

Wheelchair Accessible Vacation Homes in Chicago

Over 2700+ Wheelchair Accessible Vacation Homes in or Near Chicago
Property Image From $969
         

10.0 (102 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Property Image From $1,516
         

10.0 (1 Review)
Apartment
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  • Parking
  • Pool
Property Image From $239
         

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9.8 (181 Reviews)
Bed & Breakfast
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Property Image From $1,882
         

10.0 (53 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $125
         

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8.5 (10 Reviews)
Apartment
  • Air Conditioner
  • Wheelchair Accessible
  • Child Friendly
Property Image From $172
         

10.0 (45 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Property Image From $77
         

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10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Wheelchair Accessible

Chicago Varoom and Airbnb Places to Stay Under $200

Over 2646+ Chicago Varoom and Airbnb Places to Stay Under $200
Property Image From $162
         

8.4 (19 Reviews)
Apartment
  • Air Conditioner
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  • TV
Property Image From $150
         

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9.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Child Friendly
Property Image From $199
         

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9.0 (1711 Reviews)
Hostel
  • Air Conditioner
  • Parking
  • Pool
Property Image From $179
         

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10.0 (479 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
Property Image From $159
         

Property Image From $83
         

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5.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Child Friendly
  • Internet
Property Image From $76
         

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9.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Wheelchair Accessible
  • Internet

Instantly Bookable Vacation Homes in Chicago

Over 3968+ Instantly Bookable Vacation Homes in or Near Chicago
Property Image From $285
         

Property Image From $190
         

10.0 (6 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $266
         

9.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Property Image From $1,085
         

9.6 (18 Reviews)
Condo
  • Balcony/Terrace
  • Security/Safety
  • Fireplace/Heating
Property Image From $1,085
         

9.0 (13 Reviews)
Condo
  • Balcony/Terrace
  • Security/Safety
  • Child Friendly

About Chicago Vacation Rentals

With more than 6958 Chicago vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Allinclusivebeachresorts 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 Chicago.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Allinclusivebeachresorts 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 Chicago. Places to stay near Chicago are 739.14 ft² on average, with prices averaging $384 a night.

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

Type Count
Holiday Apartments 4372
Vacation Homes 1071
Hotels with Suites 866
B&B 54
Resorts 34
Hostels 21
Villas 9
Cottages 4
Others 3
Cabin Rentals 2

Use these Quick Filters to Find a Vacation Rental in Chicago

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

Weather in Chicago

View the weather forecast for Chicago before booking your 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