Chicago Arts District Holiday Rentals

Compare Villas, Resorts, & Rentals in Chicago Arts District, Chicago, Illinois, USA

New Zen 5 Bedroom Family Escape
House
Zen 5 Bedroom Family Escape
From US $464 per night
New
5 Bedrooms 17 Guests
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Lux Apts with Lake Views and Top Amenities
Apartment
Lux Apts with Lake Views and Top Amenities
From US $1,582 per night
|
10.0 (4 Reviews)
13 Bedrooms 32 Guests
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The Publishing House B&B
Bed & Breakfast
The Publishing House B&B
From US $230 per night
|
9.8 (186 Reviews)
1 Bedroom 2 Guests
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New Gym, Garage Parking, Balcony, Sleeps 4
Apartment
Gym, Garage Parking, Balcony, Sleeps 4
From US $313 per night
New
2 Bedrooms 4 Guests
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Mccormick Place Guest House
House
Mccormick Place Guest House
From US $77 per night
|
8.8 (42 Reviews)
1 Bedroom 2 Guests
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New Gym | Garage Parking | Balcony | Sleeps 6
Apartment
Gym | Garage Parking | Balcony | Sleeps 6
From US $303 per night
New
2 Bedrooms 6 Guests
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Villa Dubois Guest House
House
Villa Dubois Guest House
From US $88 per night
8.6 (76 Reviews)
1 Bedroom 2 Guests
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New Arcade, Free Parking, Sleeps 8!
Apartment
Arcade, Free Parking, Sleeps 8!
From US $324 per night
New
2 Bedrooms 8 Guests
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Freshly Minted 2BR - Elegance & Comfort in Central Chicago
Apartment
Freshly Minted 2BR - Elegance & Comfort in Central Chicago
From US $349 per night
|
10.0 (2 Reviews)
2 Bedrooms 6 Guests
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Hamaline Luxury Guest House
Villa
Hamaline Luxury Guest House
From US $289 per night
|
10.0 (2 Reviews)
3 Bedrooms 6 Guests
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Luxury 2BD-2BA View-Gym-Rooftop
Apartment
Luxury 2BD-2BA View-Gym-Rooftop
From US $590 per night
|
10.0 (1 Review)
2 Bedrooms 4 Guests
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Gilean Urban Retreat
Apartment
Gilean Urban Retreat
From US $566 per night
|
10.0 (1 Review)
3 Bedrooms 6 Guests
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52nd Floor MagMile Penthouse VIEWS Fireplace Pool
Apartment
52nd Floor MagMile Penthouse VIEWS Fireplace Pool
From US $280 per night
10.0 (402 Reviews)
1 Bedroom 4 Guests
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53 Floor MagMile Penthouse Views, Balcony, Pool
Apartment
53 Floor MagMile Penthouse Views, Balcony, Pool
From US $283 per night
10.0 (241 Reviews)
2 Bedrooms 6 Guests
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Modern River West 2BR with W&D by Zencity
Apartment
Modern River West 2BR with W&D by Zencity
From US $77 per night
|
10.0 (1 Review)
2 Bedrooms 3 Guests
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Art Villa
Apartment
Art Villa
From US $1,030 per night
|
10.0 (2 Reviews)
1 Bedroom 2 Guests
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Chic River North Condo 2BR 2BA with Private Balcony
Apartment
Chic River North Condo 2BR 2BA with Private Balcony
From US $295 per night
10.0 (4 Reviews)
2 Bedrooms 5 Guests
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New Luxury 3 Bdr Apt in Chicago C9
Apartment
New Luxury 3 Bdr Apt in Chicago C9
From US $1,516 per night
10.0 (1 Review)
3 Bedrooms 6 Guests
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Chicago luxury home suites
Apartment
Chicago luxury home suites
From US $1,145 per night
10.0 (1 Review)
1 Bedroom 2 Guests
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2 Bedroom Home near West Loop with Parking
Apartment
2 Bedroom Home near West Loop with Parking
From US $352 per night
10.0 (1 Review)
2 Bedrooms 4 Guests
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Cabin 105 by 747 Lofts
Apartment
Cabin 105 by 747 Lofts
From US $150 per night
10.0 (1 Review)
1 Bedroom 2 Guests
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River North Central Home With Balcony
Apartment
River North Central Home With Balcony
From US $208 per night
10.0 (4 Reviews)
2 Bedrooms 5 Guests
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South Loop Rooftop With In and Out Parking 2
Apartment
South Loop Rooftop With In and Out Parking 2
From US $307 per night
10.0 (1 Review)
2 Bedrooms 5 Guests
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Downtown Penthouse Lake Views #1|Gym, Parking+Pool
Condo
Downtown Penthouse Lake Views #1|Gym, Parking+Pool
From US $578 per night
10.0 (3 Reviews)
2 Bedrooms 7 Guests
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Spacious and Modern 3BD 2BA Home- Garage Parking!
Apartment
Spacious and Modern 3BD 2BA Home- Garage Parking!
From US $299 per night
10.0 (1 Review)
3 Bedrooms 8 Guests
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2BR Retreat in Downtown + City Skyline Views
Apartment
2BR Retreat in Downtown + City Skyline Views
From US $501 per night
10.0 (3 Reviews)
2 Bedrooms 5 Guests
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River North Rooftop With In and Out Parking 6
Apartment
River North Rooftop With In and Out Parking 6
From US $260 per night
10.0 (1 Review)
2 Bedrooms 7 Guests
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Elegant 2BR with Resort Amenities & City Views
Apartment
Elegant 2BR with Resort Amenities & City Views
From US $467 per night
10.0 (3 Reviews)
2 Bedrooms 7 Guests
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Free Parking! Private Rooftop! 3bd near downtown!
Apartment
Free Parking! Private Rooftop! 3bd near downtown!
From US $153 per night
10.0 (1 Review)
3 Bedrooms 6 Guests
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2BR near Riverwalk + downtown access
Apartment
2BR near Riverwalk + downtown access
From US $408 per night
10.0 (3 Reviews)
2 Bedrooms 7 Guests
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1F Cozy Home in Little Italy near Downtown West Loop United Center
Apartment
1F Cozy Home in Little Italy near Downtown West Loop United Center
From US $172 per night
|
9.9 (74 Reviews)
3 Bedrooms 6 Guests
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River North Private Balcony With In and Out Parking
Apartment
River North Private Balcony With In and Out Parking
From US $244 per night
10.0 (3 Reviews)
2 Bedrooms 5 Guests
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Avenir West Loop Penthouses with Iconic City Views
Apartment
Avenir West Loop Penthouses with Iconic City Views
From US $1,192 per night
|
9.8 (6 Reviews)
10 Bedrooms 24 Guests
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Sage Modern Apartments Near Union Park in West Loop
Apartment
Sage Modern Apartments Near Union Park in West Loop
From US $336 per night
|
9.7 (14 Reviews)
6 Bedrooms 15 Guests
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Modern 2BR in The Loop + Panoramic City Views
Apartment
Modern 2BR in The Loop + Panoramic City Views
From US $520 per night
10.0 (2 Reviews)
2 Bedrooms 4 Guests
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Cozy 1 BR 1 Parking Sleeps 4
Apartment
Cozy 1 BR 1 Parking Sleeps 4
From US $265 per night
9.7 (10 Reviews)
1 Bedroom 4 Guests
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Stylish 2BR Retreat in Fulton Market for Getaways
Apartment
Stylish 2BR Retreat in Fulton Market for Getaways
From US $520 per night
10.0 (2 Reviews)
2 Bedrooms 5 Guests
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About Casai's Private Villas and Holiday Rentals in Chicago Arts District

Discover more than 3389 vacation rentals available in Chicago Arts District. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Chicago Arts District.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Chicago Arts District, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Chicago Arts District. On average, places to stay near Chicago Arts District offer 733.21 ft², with nightly prices averaging US $355.

With Casai, finding and comparing holiday rentals in Chicago Arts District is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

Frequently Asked Questions About Chicago Arts District?

What are the top holiday rentals in Chicago Arts District?

How many Casai.com holiday rentals are available in Chicago Arts District?

As of 2025, Casai boasts over 3389 properties listed in the Chicago Arts District area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Chicago Arts District.

Nearby Neighborhood (12)

Neighborhood Property Count
Downtown Chicago Vacation Rentals in Chicago, Illinois 2325
The Loop Vacation Rentals in Chicago, Illinois 1334
Near North Side Vacation Rentals in Chicago, Illinois 752
South Loop Vacation Rentals in Chicago, Illinois 388
River North Vacation Rentals in Chicago, Illinois 386
Lakeview Vacation Rentals in Chicago, Illinois 316
West Loop Vacation Rentals in Chicago, Illinois 239
Lincoln Park Vacation Rentals in Chicago, Illinois 176
Hyde Park Vacation Rentals in Chicago, Illinois 110
O'Hare Vacation Rentals in Chicago, Illinois 72
Gold Coast Vacation Rentals in Chicago, Illinois 45
Magnificent Mile Vacation Rentals in Chicago, Illinois 4128

There are 3389 Chicago Arts District, IL Vacation Rentals

Recently Booked Hotels, Resorts, or Rentals in Chicago Arts District