Luxury Rentals in Chicago

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

Find the Best Luxury Rentals for Your Chicago Trip

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

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  • FAMILY FRIENDLY Luxury Rentals
  • PET-FRIENDLY Luxury Rentals
9.4 (14 Reviews)
House
: The Wolcott : Modern Elegance at Its Finest
  • Air Conditioner
  • Parking
  • Designated Smoking Area
US
View Availability
9.4 (14 Reviews)
House
: The Wolcott : Modern Elegance at Its Finest
  • Air Conditioner
  • Parking
  • Designated Smoking Area
US
View Availability
9.4 (14 Reviews)
House
: The Wolcott : Modern Elegance at Its Finest
  • Air Conditioner
  • Parking
  • Designated Smoking Area
US
View Availability
VIEW ALL RENTALS

Top Rated Activities & Tours in Chicago

Chicago River Architecture: History and Sightseeing Cruise
Chicago River Architecture: History and Sightseeing Cruise
10
Excellent
16032 Reviews
5 star rating Recommendation
From
US $39 Per Person
Reserve
Chicago Architecture River Cruise
Chicago Architecture River Cruise
10
Excellent
16060 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
2064 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
5863 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

Luxury 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 Luxury 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

9.4 (14 Reviews)
House
: The Wolcott : Modern Elegance at Its Finest
  • Air Conditioner
  • Parking
  • Designated Smoking Area
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.

Thursday May 21

Chicago, Illinois

Thu
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11.2°C
Fri
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11.8°C
Sat
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13.2°C
Sun
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18.0°C
Mon
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16.2°C
Tue
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18.7°C
Wed
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18.7°C

Frequently Asked Questions

What are the top rated Luxury Rentals in Chicago?
What are the best pet-friendly luxury rentals in Chicago?
Do any luxury resorts or villas in Chicago have a pool?

Yes, there are more than 7869 luxury resorts & villas rentals in Chicago that have indoor/outdoor and private swimming pools. Check out our filter option and find your best places to stay near Chicago.

What are some great luxury places to stay in Chicago that have internet access?
How many luxury rentals with hot tubs are available for rent in Chicago?

There are more than 7869 luxury rentals with hot tubs available for rent in Chicago.

More Luxury Rentals You May Like for Trips to Chicago

9.4 (14 Reviews)
House
: The Wolcott : Modern Elegance at Its Finest
  • Air Conditioner
  • Parking
  • Designated Smoking Area
US
View Availability
Explore more accommodations