Luxury holiday rentals in Chicago
Find and book unique properties on Luxury Holidays
Guest favourites
Featured luxury properties in Chicago
High-quality residences with premium amenities and tailored services for effortless stays.
Collection Size
406 properties
Handpicked stays across Chicago
Average Bedrooms
4+
Room to spread out and reconnect.
Reviews
27,310
Guest reviews for properties in Chicago
Average Rating
4.75 / 5
Based on 27,310 reviews.
Popular amenities for Chicago rentals
Kitchen (406)
Wifi (405)
Smoke Alarm (406)
Carbon Monoxide Alarm (406)
Hot Water (405)
Essentials (405)
Dishes And Silverware (400)
Tv (398)
Iron (397)
Microwave (395)
Hair Dryer (395)
Heating (394)
Places to stay in Chicago
406 stays
Spacious Apartments for Groups w/ Skyline Views
Property in Chicago
5.0
5 beds
4 baths
13 guests
USD 1,469
/ night
Lincoln Park – Amazing Game Room – Best Location
Property in Chicago
5.0
4 beds
3 baths
16 guests
USD 803
/ night
South Loop 5BR Luxury Suite for 12 Near McCormick
Property in Chicago
5.0
5 beds
4 baths
12 guests
USD 586
/ night
Parisian Retreat near University of Chicago Campus
Property in Chicago
4.0
3 beds
2 baths
6 guests
USD 549
/ night
Luxury Designer Penthouse NW | Pool | Gold Coast
Property in Chicago
4.9
3 beds
2 baths
10 guests
USD 598
/ night
Luxury 6BR/3BA Group Stay in McCormick | Sleeps 12
Property in Chicago
5.0
6 beds
3 baths
12 guests
USD 769
/ night
Spacious 6BR Suite Near McCormick & Soldier Field
Property in Chicago
5.0
6 beds
4 baths
12 guests
USD 592
/ night
Pristine Gold Coast 3BD|2BA | Free Parking| Beach.
Property in Chicago
5.0
3 beds
2 baths
6 guests
USD 611
/ night
Huge 6-Bedroom Retreat on the Park
Property in Chicago
5.0
6 beds
4 baths
16 guests
USD 571
/ night
Spectacular Gilded Age Gold Coast Mansion w/Deck
Property in Chicago
4.8
6 beds
4 baths
16 guests
USD 1,381
/ night
Stunning Views! New Penthouse w/ Pool & Fireplace
Property in Chicago
4.8
2 beds
3 baths
6 guests
USD 508
/ night
Perfect Location Across from Park & Train Station
Property in Chicago
4.5
5 beds
3 baths
13 guests
USD 442
/ night
FAQs
Planning your stay
Everything you need to know before booking your luxury rental in Chicago.
How many luxury listings are available in Chicago?
Luxury Holidays currently features 406 curated luxury holiday rentals in Chicago.
What amenities come with luxury rentals in Chicago?
Expect premium amenities including high-speed Wi-Fi, fully-equipped kitchens, and concierge assistance. Many properties add private pools and dedicated parking.
How do I book a luxury rental in Chicago?
Share your travel dates and requirements with our team. We will confirm availability, arrange secure payment, and coordinate your stay.
What is the average guest rating for luxury rentals in Chicago?
Guests consistently rate luxury rentals in Chicago an average of 4.8 out of 5 stars, based on 27,310 reviews.
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