Vacation Rentals in Chicago

Stay in a Vacation Rentals in Chicago – Plan Your Next Vacation to Chicago Today!

Find the Best Vacation Rentals for Your Chicago Trip

Smartours makes it easy to discover stays that match your style, budget, and location.

  • Vacation Rentals
  • Luxury Vacation Rentals
  • FAMILY FRIENDLY Vacation Rentals
  • PET-FRIENDLY Vacation Rentals
3 (193 Reviews)
House
Homan Square
  • Parking
  • Child Friendly
  • Internet
US
View Availability
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10 (25 Reviews)
House
Wrigleyville Inn
  • Air Conditioner
  • Parking
  • TV
US
View Availability
3 (193 Reviews)
House
Homan Square
  • Parking
  • Child Friendly
  • Internet
US
View Availability
|
10 (25 Reviews)
House
Wrigleyville Inn
  • Air Conditioner
  • Parking
  • TV
US
View Availability
|
10 (12 Reviews)
Apartment
Uptown Gem
  • Air Conditioner
  • Parking
  • Pool
US
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10 (25 Reviews)
House
Wrigleyville Inn
  • Air Conditioner
  • Parking
  • TV
US
View Availability
9.6 (62 Reviews)
Apartment
The Avondale Lower Level
  • Air Conditioner
  • Parking
  • Pet Friendly
US
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9.6 (62 Reviews)
Apartment
The Avondale Lower Level
  • Air Conditioner
  • Parking
  • Pet Friendly
US
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Top Rated Activities & Tours in Chicago

Chicago River Architecture: History and Sightseeing Cruise
Chicago River Architecture: History and Sightseeing Cruise
10
Excellent
16066 Reviews
5 star rating Recommendation
From
US $40 Per Person
Reserve
Chicago Architecture River Cruise
Chicago Architecture River Cruise
10
Excellent
16066 Reviews
5 star rating Recommendation
From
US $39 Per Person
Reserve
Chicago Food Tour: Deep Dish Pizza, Beer, Brownies, and More
Chicago Food Tour: Deep Dish Pizza, Beer, Brownies, and More
10
Excellent
2075 Reviews
5 star rating Recommendation
From
US $84 Per Person
Reserve
Chicago Architecture Center River Cruise aboard First Lady
Chicago Architecture Center River Cruise aboard First Lady
10
Excellent
5882 Reviews
5 star rating Recommendation
From
US $57 Per Person
Reserve

Why Book Your Trip to Chicago with Smartours?

Here’s why smart travelers plan travel with Smartours

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Smarter Stays

Vacation Rentals selected for comfort, location and value – giving you the ideal base for your adventures.
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Smarter Itineraries

AI-powered trip plans that bundle accommodations, transport, and activities into flexible packages you can tailor to your style and budget.
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Smarter Exploration

Self-guided itineraries filled with local insights, hidden gems, and authentic experiences beyond the typical tourist trail.

How to Book Your Stay in Chicago?

What’s the Smartours booking process?

Our platform connects you to a curated selection of Vacation Rentals in Chicago. Once you’ve found your ideal property, you’ll be redirected to our trusted booking partner to complete your reservation securely and with confidence.

Booking Steps

01

Search Stays

Use Smartours filters to find accommodations that match your style, location preferences, and budget.
02

View Details

Click on a listing to see photos, amenities, reviews, and pricing.
03

Book Securely

Follow the link to finalize your reservation directly with our verified booking partner.
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Indoor Features

  • Fully equipped kitchens or kitchenettes
  • Comfortable living areas with smart TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-room coffee and tea facilities
  • Premium bedding for restful nights
  • Modern bathrooms with walk-in showers or soaking tubs

Outdoor Amenities

  • Balconies, terraces, or rooftop lounges with scenic views
  • Swimming pools, either private or shared
  • Outdoor dining spaces with BBQ or grill access
  • Gardens or courtyards for relaxing downtime
  • On-site parking or easy transport access
  • Proximity to key attractions, markets, or nature trails

Other Places to Stay in Chicago

3 (193 Reviews)
House
Homan Square
  • Parking
  • Child Friendly
  • Internet
US
View Availability
|
10 (25 Reviews)
House
Wrigleyville Inn
  • Air Conditioner
  • Parking
  • TV
US
View Availability
Explore more accommodations

Seasonal Weather in Chicago

What’s the weather like in Chicago throughout the year?

Chicago’s climate varies by region, but most areas enjoy mild to warm weather year-round. Coastal cities benefit from ocean breezes, while inland areas and the desert see greater temperature swings between day and night.

Saturday May 23

Chicago, Illinois

Sat
weather-icon
13.5°C
Sun
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14.3°C
Mon
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17.6°C
Tue
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20.6°C
Wed
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18.3°C
Thu
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18.3°C
Fri
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16.1°C

Frequently Asked Questions

What are the top rated Vacation Rentals in Chicago?
Which is the best family rental in Chicago?

There are many large, family-friendly vacation homes available in Chicago; however, here are the most popular family rentals listed on our site:

Can we get self-catering vacation rentals in Chicago?

Yes, there are 9592 self-catering vacation homes in Chicago that have hot tubs, swimming pools, & other amenities.

What are the best luxury vacation rentals near Chicago?

There are more than 9592 luxury villas and vacation homes in or near Chicago. Filter by price to compare find the most expensive places to stay on Smartours.

Can we bring our dog to our vacation rental in Chicago?

Yes, there are 9592 pet friendly vacation homes and places to stays that are available in or near Chicago that you may consider.

More Vacation Rentals You May Like for Trips to Chicago

3 (193 Reviews)
House
Homan Square
  • Parking
  • Child Friendly
  • Internet
US
View Availability
|
10 (25 Reviews)
House
Wrigleyville Inn
  • Air Conditioner
  • Parking
  • TV
US
View Availability
Explore more accommodations